The Best of Italy: Ultimate Two Week Italy Itinerary (14 Days)

Grand Canal in Venice from Acadamia Bridge during sunset

Ahh, the land of pizza, pasta, and gelato – what’s not to love about Italy? This boot-shaped country boasts so much to see, that it’s difficult to plan an itinerary for a limited amount of time. So, in an effort to take the guesswork out of it for others, I’ve put together this epic two week Italy itinerary for fourteen glorious days in Italy, now that I’ve visited multiple times. It hits all the main sights – Rome, Florence, and Veniceplus some extras so you can come back home seeing more than the bare minimum.

Statue and fountain in Piazza Navona, Rome, Italy
Colorful houses in Positano, Amalfi Coast
View over gardens of Villa Rufolo in Ravello, Amalfi Coast

Now, I have to warn you. This two week Italy itinerary is super detailed. Like, how-the-hell-do-you-have-time-to-write-all-this detailed. And I did that on purpose. You can go to any old website to get a vague “two nights in here” and “one night here,” bare-bones itinerary for Italy. But those itineraries don’t tell you what to do in each place, or how to get from each city to city. You’d have to go look that up after. But not with this itinerary.

Basically, what I’m trying to say is: get ready for a long article! (About a 30 minute read.) You might definitely want to save this for later right now by bookmarking it or saving it on Pinterest, just in case you don’t finish all in one go. Then, grab a cuppa, sit back, and let’s get to it!

Pssst! Debating a shorter trip to Italy? Definitely skim through my detailed itineraries for ten days in Italy or one week in Italy.

The Perfect Two Week Itinerary

Let’s start off with an overview of this epic, fourteen day Italy itinerary, so you can have an idea what to expect.

DaysCityOvernight In
Days 1 – 3RomeRome
Days 4 – 6Pompeii & Amalfi CoastAmalfi Coast
Day 7CapriFlorence
Days 8 – 9FlorenceFlorence
Days 10 – 11Pisa & Cinque TerreCinque Terre
Days 12 – 13VeniceVenice
Day 14MilanMilan

If you’re the average traveler with limited vacation days, I suggest breaking it down like below. This way, you only need to use ten vacation days, but you get fourteen actual days in Italy.

14 day itinerary and 2 week itinerary for Italy

What is the Best Time of Year to Visit Italy?

The absolute best time to visit Italy is definitely the shoulder seasons of April – May and September – October. This allows you to see everything in comfortable weather, but to avoid the extreme crowds (And heat! And prices!) of the summer. If you plan to swim, aim for September – October, so that the water has had all summer to get warm.

Milan Duomo Cathedral with green palm leaves in front
Gelato in front of the Cathedral in Florence, Italy
Boat on Venice Grand Canal viewed from Acadamia Bridge

That being said, I’ve traveled to Italy in the middle of August and still had a wonderful time. So if July and August are the only time you have available, you’ll still have a great trip. Just come mentally prepared for the crowds.

Winter in Italy is generally warmer than winter in central Europe. However, I would avoid winter if possible for this itinerary. There are places that flood often during rain (Venice) and places that practically shut down out of peak season (Cinque Terre and the Amalfi Coast). If you can’t stand large crowds, I would also avoid Easter in Rome. Other than that, any time in Italy is a great time to visit Italy!

If you have more specific questions about your trip timing and what I think, definitely leave a comment at the bottom of this page. I’ll get back to you with my advice. Think of me like a free travel agent…!

Best Way to Get Around Italy?

One of my favorite things about Italy is how ridiculously easy it is to travel Italy without a car. This country gets a lot of slack for being inefficient and disorganized, but you have to admit, they do public transport just fine! This itinerary is completely car-free, relying solely on trains, buses, and ferries.

In my opinion, trains are the best way to travel Italy. This is especially true for your first time in the country. I do have dreams to one day complete a grand Italian road trip. But that is only because, after multiple trips, I now have places on my list that are remote and therefore easier to reach by car. All the more-typical destinations are much easier to visit without the hassle of Italian driving, filling up gas, finding and paying for parking, etc.

One very important tip for train travel in Italy is to always validate your ticket! Otherwise, you will be fined, and the fines ain’t cheap. (Like, truly. The fines are low-key high-key ridiculous.) How do you validate your train ticket in Italy? Simply stick the paper ticket into the machines before you enter the train. It’ll make a noise and time-stamp your ticket. These little validation machines are typically at the entrance to each platform. If you have trouble locating them, just ask a train station employee. If you buy your ticket online or via the mobile app – no need to stress!

In this itinerary, I include all the details and prices for each time you’ll use public transport to move around. I’ve got you covered!

Free Printable 2-Week Italy Itinerary E-Book

But once actually in Italy, you definitely don’t want to be walking around on your phone all trip trying to get to each next spot. So, I’ve made a printable, condensed version of this post with every important detail from this fourteen day Italy itinerary you’re about to read. Just download the PDF, print it double-sided (so four pages total), and you’re good to go for your trip. It even has a map! Click below to get it emailed to you.

Italy 2-Week Itinerary Free PDF

(Finally) The Actual Two Week Itinerary for Italy

Beforehand, I just want to let you know you can do this itinerary in the order I have it or the reverse. Just look up flights and see which direction is cheaper. Also, at the very end of this page, I have a section on how to adjust this itinerary if you need to. Ready?!


Rome. The Eternal City. This place needs no introduction, since I’m sure you learned plenty about it in school. As the former capital of the Roman Empire and the current capital of Italy, Rome is a mix of old and new like you’ve never seen. Huge, crumbling ruins from 2000 years ago contrast against beeping Vespas zipping through the cobblestoned streets. Try to ignore the street vendors with no regard for personal space selling selfie sticks and whizzing gadgets, and I’m sure you’ll fall in love with Rome as I have.

Roman Colosseum

How to Get to Rome

This is the start of your trip, so you’ll need to fly in. Rome has two airports, so be careful you fly into the correct one. The main international airport in Rome is Fiumicino (FCO). This airport is the further out one. To get to the city center from FCO, you have two options.

  • Option 1: Take the train. Follow signs in the airport to the train platform. From FCO, take the train to Roma Termini train station. This costs €14 and will take 30 minutes. From Roma Termini, you can either walk to your accommodation, or use the Metro to take the subway if your accommodation is further away. Be very careful of pick-pocketers in this train station! Do not accept or ask help from anyone except official employees, and wear your backpack facing your front.
  • Option 2: Take a taxi. Taxis from FCO into central Rome are a fixed fare of €48. Make sure you get into an official taxi at the taxi pickup line. They should accept card, and you can double check this as well as fare before getting in. This will take 30 minutes, just like the train.

Rome’s other airport is Ciampino (CIA). This smaller airport is actually slightly closer to central Rome. However, it is only used for budget airline flights within Europe, like RyanAir and EasyJet. If you’re flying here (or anywhere!) with RyanAir, definitely skim through my guide on how to not get ripped off! Once again, you have two options on how to get to central Rome from CIA airport.

  • Option 1: Take a bus to (right near) Roma Termini train station. There are multiple options you can explore here. Some include SITBusShuttle for €6 one-way, or Terravision for €4 if purchased online or €6 in person. This ride takes 40 minutes.
  • Option 2: Take a taxi. Taxis from CIA into central Rome are a fixed fare of €30. Again, make sure you get into an official taxi at the taxi pickup line and confirm the fare before getting in. This ride takes 30 minutes.

What to Do in Rome (Three Days)

Three days in Rome is the minimum amount of time to “see everything.” Below is exactly how to see Rome in three days. Take it easy on day one, since it’s the day your flight gets in. But feel free to interchange days two and three as works best for you. If you get in way too late on day one, you can tack it onto day three.

Day One

Walking straight through this route as I have it below is 30 min (2km or 1.25 miles), just to give you an idea of total distance on day one. Start at whichever end is closer to you.

  • Scalina Spagna: Otherwise known as the Spanish Steps, this beautiful staircase gets busy at night as a popular hang-out spot.
  • Trevi Fountain: This is Rome’s largest and most-famous fountain. Prepare for major crowds, and start practicing major patience needed to get your perfect pic!
  • Pantheon: Built in 120AD as a Roman (pagan) temple for all gods, it was transformed into a church in 609 AD. Still, everyone calls it the Pantheon, which means “honor all Gods” in Greek. Free to enter!
  • Piazza Navona: I’m pretty sure this square is just popular because it’s beautiful! Lots of cafes line the edges of the piazza, which also has two impressive fountains, and a church in between them.
  • Largo di Torre Argentina: This is where Roman senators assassinated Emperor Julius Caesar by stabbing him 23 times (dramatic much?) to death in 44 BC.

Day Two

  • Colosseum: Gladiators. Need I even say more?! Though it is now in ruins, back in its heyday, this thing sat 50,000 guests and even had retractable shades. Tickets are €16 for this plus the next two sites, plus €2 if purchased online from the official site. But, unless you plan to be the first ones at the door, I highly recommend skip-the-line tickets. They are €22 here, or €37 for a guided tour. These price quotes are the highest prices, but those 25 years and younger get discounts!
  • Roman Forum: These are the ruins of numerous important government buildings during the ancient Roman Empire. It’s so cool walking around, seeing how huge the ruins are, and wondering how it must have been back then – almost 2000 years ago!
  • Palatine Hill: This is where all the cool kids lived during the Roman Empire – the aristocrats and emperors and all that jazz.
  • Arch of Constantine: This arc, built in 302 AD and the largest surviving one of its kind, is right outside the Colosseum.
  • Via dei Fori Imeriali: This street is my favorite part of Rome, especially at dusk! You can look down on the Roman Forum from above on one side and view other incredible ruins on the other. It connects the Colosseum to the next attraction below.
  • Vittoriano: This huge, marble building almost doesn’t fit in with its ancient surroundings.  But I love it, nevertheless. It is a memorial to Victor Emmanuel II, the first king of the united Italy as we know it today.

Day Three

  • Vatican City: Technically, this area isn’t Italy! It’s its own country – the smallest country in the world – and it’s ruled by the Catholic Pope. There are basically three things to see while here: St. Peter’s Square, St. Peter’s Basilica, and the Vatican Museums. St. Peter’s Basilica is free to enter, but dress code is very strict. Make sure your shoulders and knees are covered. This goes for all genders and ages. There is a slow moving-crowd-slash-line to get in, but I found it moved quickly enough when I went. Once in the basilica, you can climb up to the dome for iconic views. To the right from the entrance, there should be a “Cupola” sign. Follow the sign until at the ticket office, where you can purchase a ticket to either climb the whole way or one to take an elevator halfway up. As far as I know, you can only buy tickets on site, and they should be around €8 and €10. The Vatican Museums house the world-famous Sistine Chapel. You’ll pay €17 for entry at the door, but definitely pay €21 for a skip-the-line ticket purchased online. Entry to the Museums is free on the last Sunday of every month and on World Tourism Day (Sept 27). Seeing Vatican City should take up a whole morning.
  • Castel Sant’Angelo: Emperor Hadrian originally commissioned this as a mausoleum for himself and his family, but it’s since been used as a fortress, castle, and currently a museum. I didn’t enter the museum, so I can’t recommend entering, but I think this castle over the river just looks so cool!
  • Wander: Explore on your own! Get lost! You’ve checked off all the “can’t miss” things everyone else does, but who wants their trip to be just the same as everyone else’s? If you just run around ticking off attractions, I’m not sure you’ll like Rome. But wandering it’s less-crowded streets, strolling along the river, popping into a random church – these are the things that will leave you loving Rome.

What to Eat in Rome

Food in Italy is good just about everywhere. But each region is known for something different, so why not try all your favorite Italian dishes (and some new ones!) right in the specific regions or cities that they were invented? So throughout this guide, I will be listing and explaining some must-try foods from each place you will be overnight-ing. To start, here are some traditional Roman foods to keep an eye for while in Rome!

  • Spaghetti alla Carbonara: This famous Roman dish actually arrived on the Italian scene relatively recently, in the mid-1900s. It is made by mixing whisked eggs and grated cheese into cooked spaghetti, then adding in cured pork, and topping with black pepper and, of course, some more cheese.
  • Cacio e pepe: The name of this Roman dish translates literally into “cheese and pepper,” and that’s a pretty good description of what it is!
  • Pizza al taglio: While pizza itself was not invented in Rome (don’t worry – you’ll stop by the city where it was born later on in this Italy itinerary!), pizza by the slice, or pizza al taglio, was. But it looks far different to the triangularly-sliced pizza you may be used to back home. Here, the slices are rectangular, and they often come piled high with meats and/or vegetables. It’s considered street food, so it makes the perfect quick lunch if you don’t have enough time for a sit-down meal as you explore the attractions in Rome.
  • Supplì: These are another perfect Roman snack to grab while on the go! They are fried, breaded balls of seasoned rice with cheese and sometimes meat inside (essentially, croquettes).
  • Bruschetta: This beloved Italian appetizer does not hail from Rome itself, but its origins date back to the Roman Empire, or perhaps even the Etruscans who preceded it. Regardless, as the capital of the Roman Empire, Rome makes a pretty good place to try some authentic bruschetta alla Romana, which is grilled bread rubbed with garlic and topped with olive oil. Of course, no one will blame you if you get the version with tomatoes as well!


Pompeii was an ancient Roman city, famous now for coming to its demise after a tragic volcano eruption. The city, along with nearby Herculaneum, was preserved under all the ash. It has since been excavated, which allows visitors to see a frozen-in-time snapshot of Roman civilization almost 2000 years back!

Large statue of male head and ruins in Pompeii

How to Get to Pompeii from Rome

First, take an early train from Roma Termini train station to Napoli Centrale train station. This takes either one, two, or three hours, depending on what type of train you take! Naturally, the costs are different, too. If you are buying a ticket for the next morning, you can expect to pay €13 for a 3-hour Regional train, €27 for a 2-hour Intercity train, or €48 for a 1-hour Frecciarossa train. If you are buying one month out, the prices for the faster trains drop to €20 for a 2-hour Intercity train, or €25 for a 1-hour Frecciarossa train. And if you buy three months out, the 2-hour Intercity train drops to €15.

Moral of the story? Always buy your long-distance train tickets online as soon as you know your schedule to save money in Italy! If you are taking regional trains, just buy them at the station on the day of, to allow flexibility in case plans change.

OK! So once you arrive at Napoli Centrale, follow signs to the connected underground station called Napoli Piazza Garibaldi. From here, take the Circumvesuviana train for 40 minutes to Pompeii Scavi Station for €3.20. (This part was honestly very confusing for me! I accidently went to the Metro 2 area instead of the Circumvesuviana area. So my tip to you is to ignore the Metro 2 signs, and ask for help from staff if you need to.)

At Pompeii Scalvi train station, there is a luggage storage service. Drop your bags off here for €8 per bag. From here, it’s a 5-minute walk to the Pompeii site.

What to Do in Pompeii (Half Day)

The only thing to do in Pompeii is…tour Pompeii! Entrance to this historical site costs €16, and you should plan to spend 2 – 3 hours here. You can buy tickets at the gate in person or online (for an additional fee) at the official website. You can also check opening hours for the month you are visiting on the site.

If there is any place in all of Italy where you need a tour, it is Pompeii! Otherwise, you’re really just staring at a lot of old rocks with no idea why. There are a few options on how to actually know what’s going on in Pompeii.

  • You can join a tour group by paying around €12 in cash on the day of. Guides hang out near the entrance, and the ones certified by the region of Campania have official ID badges. A private guided tour will, of course, cost more.
  • You can buy an official audio guide set at the Porta Marina entrance for around €8 and tour at your own pace.
  • You can get an audio tour for free by downloading Rick Steve’s audio guide for Pompeii. I did the live tour while in Pompeii, but I’ve used his guides for other Italian sites, and I was satisfied! It’s a great way to save money while still getting info.

While Pompeii is the more-popular site due to its much larger size, Herculaneum is actually the site that is better preserved. Personally, I only toured Pompeii, due to time constraints. But if you are a history buff and don’t mind a busy day, consider trying to squeeze both in!


Sorrento is a perfectly charming place, and it boasts seriously beautiful views over the Bay of Naples and Mt Vesuvius (that really destructive volcano way back when). However, its purpose in this itinerary is as a convenient jumping-off point for the Pompeii-Amalfi Coast-Capri area. I recommend using this as a base for the three nights to limit dragging your luggage around. However, if you prefer to be in the heart of the action, you can head straight to Positano (or Amalfi) after getting to Sorrento from Pompeii.

Hanging vines in Sorrento along the Bay of Naples

How to Get to Sorrento from Pompeii

Head back to Pompeii Scalvi train station and pick up the bags you dropped off. Then, hop back on the same Circumvesuviana train route and ride for 30 minutes and €2.40 to Sorrento. It’s the very last stop on the route, so don’t worry about missing it!

What to Do in Sorrento (Half Day)

If you decide to stay in Sorrento overnight or even use it as a base, I recommend simply walking around town at your leisure. It’s a super cute place to window shop (or actually shop), eat, and enjoy views of the Bay of Naples and Mt Vesuvius.

Amalfi Coast

I know all of Italy is stunning, but get ready for some insane beauty over the next few days exploring the Amalfi Coast! Unsurprisingly, this area is filled with lots of couples and is popular as a honeymoon destination. Though the area is named after the town of Amalfi, it is the town of Positano that truly steals the show. This area is a really special place, and it’s impressive to think about how the Italians built the curvy roads and quintesential houses into the steep cliffs.

Colorful houses in the cliffs of Positano, Italy

How to Get to the Amalfi Coast from Sorrento

There are a few options on how to do this. Two of them include an insanely curvy and crowded two-lane road, so keep that in mind as you decide, especially if you’re prone to motion sickness.

  • Option 1: Take the bus. This is the most budget-friendly option. Board the SITA bus 5071 from Sorrento (map below for exactly where). It takes either 50 minutes to Positano or 1.5 – 2 hours to Amalfi. Unfortunately, this bus is crazy crowded, even in shoulder months. You’re not guaranteed a seat, so you might have to stand. I actually had to sit on the floor of the bus and couldn’t even enjoy the views approaching Positano *tear*. If you do snag a seat, sit on the right side for better views. Bus tickets cost €10 for 24 hours unlimited rides and are sold at “tabaccherie” (cigarette shops) or newspaper stands in every town on the route. They can’t be purchased on board the bus! I recommend buying yours in Sorrento at the ticket booth at the Circumvesuviana station, since you’ll already pass through here after Pompeii. You can buy them ahead, but the 24-hours starts once you board the bus and validate your ticket. Check out the bus schedule here.
  • Option 2: Take the ferry. This is definitely the most beautiful way to pull up to each town. From Sorrento, this is 30 minutes and €15 one-way to Positano and 1 hour and €16.50 one-way to Amalfi. Though it won’t happen often, ferries get cancelled if sea conditions are too rough, so allow some flexibility in your plans. Below is a map of the ferry station in Sorrento. You can’t tell from the map, but it requires walking down a staircase. Check out the ferry schedules here.
  • Option 3: Hire a private car. This is not a cheap option, but might be worth it with a large enough group. You’ll have to search for price quotes online depending on the car size, company, and pick up and drop off locations. But as an idea, a private transfer from Rome to Positano or Amalfi might cost around €500. If you do hire a private car, I recommend including a stop in Pompeii between Rome and the Amalfi Coast. That way, you’re saving a good amount of hassle between all the train transfers, luggage holding, and buses!

What to Do in the Amalfi Coast (Two Days)

These days are totally interchangeable however you please. There aren’t a lot of “attractions,” per se, in the Amalfi Coast. The main thing to do is to just take in the beauty, whether by shopping in the tourist-geared shops, eating with a view, or taking a swim. You really can’t go wrong! But, if you like to have a plan, I recommend you split two days in the Amalfi Coast like below.

Day One

  • Positano: This unreal village is the star of the whole area. You definitely want to get here earlier rather than later, if you can, to avoid midday crowds. For the best view, splurge on a meal at Le Sirenuse Hotel’s La Sponda Restaurant.
  • The beach: After exploring during the morning, cool off from the midday heat by taking a swim. The easiest option would be the main beach right in front of the town, Marina Grande beach. If you have your own ride or are willing to bus back and forth 35 minutes each way, check out Furore beach. These two beaches are the most insta-famous ones in the area, but there are many more!

Day Two

  • Amalfi: This is the town after which the area is named. It boasts a beautiful church, the Amalfi Cathedral, which you can enter for €3. It’s actually pretty cool inside, but the exterior is the main show-stealer, in my opinion!
  • The Path of the Gods: I didn’t get to do this, but I really wanted to and had planned to! This hike between Amalfi and Positano takes you along the very top of the cliffs and is supposed to be ahhhmazing. Just Google “Sentiero degli Dei” and follow the route. It starts in Bomerano, which you can reach by SITA bus from Amalfi. It ends in Nocelle, the upper part of Positano. I definitely recommend doing it this direction, since it’s all downhill, and you’ll get better views. Definitely check out the official page for more deets if you’re interested.
  • Ravello: This tiny little village high up in the mountains has the area’s most famous villa – Villa Rufolo. Entry costs €7, and you can take the SITA bus 5110 from Amalfi. The ride takes 25 minutes.

What to Eat in the Amalfi Coast (and Nearby)

These are some traditional Italian foods from the Amalfi Coast and Naples.

  • Mozzarella di Bufala: This famous Italian cheese is made from the milk of the Italian water buffalo, instead of milk from cows, like mozzarella without the “di bufala” is. It hails from the region of Campania (the region where Naples, the Amalfi Coast, and Capri are), but especially Salerno, a city just to the east of the Amalfi Coast. A great way to try this item would be in a caprese!
  • Lemoncello: You will find this sweet, lemon liquor practically everywhere you look upon arriving in the Amalfi Coast.
  • Pasta al Limone: With all the lemons in this area, it’s no surprise they found their way into the pasta dishes as well. This creamy dish with cheese and lemon is so unique and a must try when in the area.
  • Anything Seafood: Since this area hugs the coast, get your fill of fresh seafood pasta dishes while in this region!
  • Pizza: The birthplace of pizza is Naples, and while you won’t have time to stop for a bite when transferring from Rome to Pompeii, you might have time when transferring from Capri to Florence (covered in the next section of this itinerary). If not, the Amalfi Coast was part of the former Kingdom of Naples, so it’s the next best place to try the Italian staple. Authentic Neapolitan pizza is made in a wood oven (this part is crucial!) with only the simple ingredients of dough, tomatoes, mozzarella, olive oil, and a couple fresh basil leaves.


The celebrity-favorite island of Capri makes for the perfect final day in south Italy before your itinerary takes you up north. It’s known for yacht-studded waters, glowingly-blue grottos, and upscale shopping. Maybe just reading this hurt your bank account a little bit… but not to worry! I’ve got you covered with how to visit Capri on a reasonable budget.

View from above of Faraglioni cliffs in Capri, Italy

How to Get to Capri from the Amalfi Coast

The only way to get to Capri is by boat (it’s an island – duh!). Ferries will be from Sorrento, from Positano, and from Amalfi. Expect €24.50 for a 50-minute ride from Amalfi, and less from the other two.

You’ll need to drop your bags off in storage while you explore. You should be able to either near the main docks in Marina Grande on Via C. Colombo, or under the funicular station, past the signs for “toilette,” along the tunnel part of Via Acquaviva. This was my plan when I did this trip, but I couldn’t locate the storage place! Luckily, an Italian waiter came to my rescue and offered to hold our bags in the restaurant all day if we ate at his place. Honestly, I’m sure you would have no trouble arranging the same.

What to Do in Capri (Half Day)

There is so much to do in Capri that you’d have trouble fitting it all into a single day, let alone a half day. So you’ll have to pick and choose what interests you most from the below. The island’s official site actually has a pretty good itinerary you can follow, too.

  • Marina Grande: No need to even add this to your list. You’ll inevitably walk by this colorful harbor-front area after disembarking the ferry.
  • Boat tour around the island: This is the best way to truly appreciate Capri’s magnificent cliffs. You’ll also go past Faragolioni, that ultra-iconic arch in the water. Boat tours can also include an add-on of the Blue Grotto. Without the Blue Grotto, expect €18 for an hour-long tour.
  • Blue Grotto: This cave is probably the most famous attraction in Capri! Unfortunately though, it’s a bit of a time-suck because of that. We were told we would have to wait on a small, bobbing rowboat for an hour before our turn to enter, so we skipped the grotto, even though our boat tour included it. The only way to avoid the long wait is to be the first ones out, but the best time for viewing is noon – 2pm, so it’s quite the dilemma. Tours departing from Marina Grande cost €14.
  • Piazzetta: This is the island’s most famous square. Be sure to stroll down the Via Camerelle while in the area.
  • Anacapri: The island of Capri actually has two towns; Capri and Anacapri. Anacapri is less crowded than Capri, and it has more artisanal shops, rather than just high-end boutiques. While here, definitely pass Piazza Vittoria, the main square. You can also ride the chairlift 12 minutes to Mount Solaro for a view (€11), or walk there in 30 minutes.
  • Villa San Michele: Entry costs €7 for some spectacular views.
  • Gardens of Augustus: From here, you get that classic Capri viewpoint of the Faraglioni. Entry only costs €1!
  • Marina Picola: If you’d rather spend your half-day relaxing at the beach instead of running around the island, this beach is a classic.


As the birthplace of the European Renaissance, Florence is known for all things art. It houses world-famous masterpieces, such as the David statue by Michelangelo and The Birth of Venus painting by Botticelli. Personally, I was expecting a bit more from Florence than I got, since everyone and their mothers raaave about it in comparison to Rome. (For the record, I’m staunchly team Rome!) But maybe I’m just not into art enough? That being said, though, it’s definitely still a can’t-miss Italian destination with plenty to do.

View of Florence from Piazza Michaelangelo

How to Get to Florence from Capri

(Psst: You’ll actually be doing this transfer from Capri to Florence on the same day that you visited Capri. Then, the next day, you’ll wake up in Florence to start your two full days there. Just scroll back up to the itinerary summary at the top of this page if you’re confused!)

First, get back to Napopli Centrale from Capri. I recommend taking the ferry directly to Naples from Capri. This will be 1 hour 25 minutes for €12.30 or 50 minutes for €19.20. Then, take a taxi from the ferry station in Naples to Napoli Centrale. When I did this, the taxi cost me €20. I also stopped and picked up a pizza to go while in central Naples. After all, Naples is the exact birthplace of pizza! How could I not?!

Alternatively, you can take a ferry from Capri to Sorrento. This takes 20 or 30 minutes minutes and costs €17 or €14.40, respectively. Then, go up those stairs to the Sorrento Circumvesuviana station, and ride the Circumvesuviana train to Napoli Piazza Garibaldi for 70 minutes and €3.60. From there, walk the underground connection to Napoli Centrale. This is a little more hassle – hence why I recommend the ferry straight to Naples – but it’s cheaper.

Either way, once in Napoli Centrale train station, take a direct, 3-hour train to Firenze S. M. Novella train station. Since this is a long distance, don’t even think about taking one of the Regional or Intercity trains! These will set you back 2 – 4.5 hours. Trust me – just book the Frecciarossa train for this route as soon as you have your dates to get the cheapest price you can. As an idea, it will cost €76 if you buy the day before, €63 if you buy two weeks in advance, or €30 if you buy a month in advance.

What to Do in Florence (Two Days)

Many people recommend considering the Firenze Card, which covers a lot of attractions in the city. For two days in Florence (or even three days in Florence), the card is not worth it. Instead, I recommend purchasing the Grande Museo del Duomo ticket. This grants entry into the Duomo, a climb to the dome of the Duomo (the Cupola), a climb to the bell tower (the Campanile), entry into the baptistery, entry into the Duomo museum, and entry into the crypt beneath the church. It costs €18, plus a €2 pre-sale fee if bought on the official website.

Now that that bit’s out of the way, here’s everything to do in Florence in two days! I haven’t split it out into separate days here, because I think it’s better if you decide. Do you like to visit one museum a day, or have one big museum day? Do you want to avoid climbing stairs twice in the same day, or do you not care? Do you prefer a viewpoint for sunset, sunrise, or can’t be bothered? These are the things that will determine what you do each day, so I can’t recommend that for you. But don’t worry – most sights in Florence are rather compactly located, so planning a route shouldn’t be an issue!

*Items with an asterisk are totally skip-able if you’re not interested, but I’ve included them since they’re included in the ticket I recommended above. If you want a more-detailed breakdown of the below, plus pictures, check out my full guide on everything to do in Florence.

  • Basilica di Santa Maria del Fiore (aka, the Duomo): It’s the third largest church in the world, was instrumental in the Renaissance, and is the symbol of Florence. Entry is free, but prepare for a massive line at least an hour long.
  • Cupola: Bruneschelli’s Dome, named after the architect who designed it, is actually the most impressive part of the entire church. Architecturally, it was the first of its kind. He literally had to invent new tools and architectural systems to do it! Definitely climb up the steps for the view from the top. You’ll have to select a specific time slot, though, when you buy your ticket! Otherwise, you will be turned away and asked to return.
  • Campanile di Giotto: Yes you already climbed up the cupola, but there’s another viewpoint! This time, the view is the cupola itself.
  • Battistero di San Giovanni: This is the building right across the main cathedral. The Byzantine-like mosaic inside was actually pretty cool in contrast to all the typical-Renaissance paintings. Everyone will be snapping pics of the gold doors outside, but those are copies. The real ones are in the Duomo Museum!
  • Duomo Museum*: Since you already paid, it might be worth a quick visit. It will help you understand why all this Duomo stuff in Florence is such a big deal!
  • Crypt of Santa Reparata*: This is included in the Duomo combo ticket, which was the only reason I saw it. But once I got there, it was actually much more than I expected! It’s basically church ruins from 405AD inside the main church. The unfortunate thing about the crypt is that you have to wait in the same line as for the free Duomo entry. So definitely time these two activities together!
  • Piazza della Repubblica: One of the main squares in Florence.
  • Piazza della Signoria: This square has a lot going on! The best part is definitely the Loggia dei Lanzi. It’s basically a free, open-air museum of dramatic sculptures that really should be in one of the museums. (Like really though, I’m super surprised these are just out there!) Also in this square is a copy of the David statue, for those of you who don’t pay to see the real thang.
  • Palazzo Vecchio: I didn’t enter except for the free courtyard. But apparently it’s supposed to have a great view of the Duomo.
  • Ponte Vecchio: This iconic bridge has become synonymous with Florence itself! It was originally a passageway so the Medicis (a super rich family that basically made Florence….well, Florence) didn’t have to walk with the commoners on their commutes from their palace. Since then, shops have been added and create the look it has today. Prepare for major crowds!
  • Piazzale Michelangelo: The best viewpoint in all of Florence – hands down! I recommend trying to time your visit with sunset, but it’s gorgeous anytime. (I went three times in my visit….so I would know.) It requires an uphill walk and is the furthest out you’ll get from the city center. So make the trek worth it! Bring some snacks and hangout for a while like everyone else does.
  • Acadamia: Unfortunately, the only reason to enter this gallery is for one piece of art. The David. Don’t at me, art fanatics. You decide if that’s worth it for you, but y’all know me! I have such FOMO that I had to pay €12 and see for myself. Pro-tip: avoid the lines AND the €4 online skip-the-line fee to book by visiting on one of the days they allow night visits! I got in lickety-split! No one really knows about it, which is why it’s so empty, so let’s try not to tell too many people? *wink* Confirm the night time hours, or book online, here.
  • Uffizi Gallery: Uffizi actually means “offices” in Italian, which makes sense, because this building used to be the Medici’s offices. Now, it’s a museum, and a world-famous one at that! Its most-famous art piece is the Birth of Venus painting. Entry costs €12, plus €4 for the skip-the-line online booking fee on the official site. Everything I read beforehand swore up and down that wait times are upwards of three hours. But when I went (mid September, early afternoon) there was no line in sight.
  • San Lorenzo Market: This is Florence’s most-famous market. Stop by here to shop leather and eat in the indoor food stalls.
  • Santa Croce: I didn’t enter this church, since admission was not free, but I do think it’s in a picturesque area and warrants passing by!
  • Palazzo Pitti: Normally, palace equals royalty…not in Florence! This palace belonged to the Medicis (shocker). I personally have seen way too many European palaces at this point. So I forwent paying the €10 entry fee and only observed from outside. But I did regret maybe not having arrived earlier in the day than I did, to buy a Boboli Gardens ticket (€6)!

What to Eat in Florence

These are some Florentine and general Tuscan traditional dishes to try while in Florence.

  • Bistecca alla Fiorentina: You will have no trouble finding Florentine-style beefsteak to try in a restaurant in Florence. Keep in mind that since it’s a pretty thick cut, getting the inside well done would be difficult without ruining the outside of the steak!
  • Gelato: Yep – everyone’s favorite frozen Italian dessert made from milk, cream, and sugar is from the city of Florence! Now, that absolutely does not mean you should wait until arriving in Florence to try authentic gelato (after all, if you’re not having gelato at least once a day, are you really even on vacation in Italy?). But, maybe it does mean taking a gelato making class at the Carpigiani Gelato Museum?
  • Biscotti: These dry, crunchy, oblong-shaped almond cookies are traditionally called cantucci. They originally come from the Tuscan city of Prato, which sits just north of Florence.
  • Crostini Neri: Also known by the names of crostini di fegatini and crostini Toscani, this typical Tuscan appetizer is toasted bread with a chicken liver paste spread atop.


Is there anything more quintessential Italy than the image of the leaning tower of Pisa? It’s funny how such a famous Italian landmark is from the most random of Italian cities! Luckily, Pisa is a necessary transfer station on the route between Florence and the Cinque Terre, so you lose almost no time making a couple-hour stop to get out of the station, snap your cliché photographs, and get right back on your way.

Leaning Tower of Pisa next to the Pisa Cathedral

How to Get to Pisa from Florence

Take a regional train from Firenze S. M. Novella train station to Pisa Centrale train station. This is a 50 minute ride and costs €8.70. Once at the train station, head to the luggage storage in the station, and drop off your things for €5 per bag. Check out the storage website.

What to Do in Pisa (Half Day)

Personally, because this two week Italy itinerary is so jam packed, I recommend you head straight to the leaning tower, snap your pics, and head back to the train. The walk is about 30 minutes each way, plus I expect you’ll spend about 20 – 30 minutes trying to get that perfect leaning picture. So budget 1.5 – 2 hours for your stop in Pisa. The reason I recommend this is so that you can have as much time as possible in Cinque Terre.

But, if you want more than just a photo, there actually are a decent amount of things to do in Pisa.

  • Climb the leaning tower: It’ll cost you €18 and you’ll need to choose a time-slot! The line looked long as I passed by.
  • Go inside the Duomo (for free!): You still have to get a ticket, though, and time slots do book out. Do this at the building with all the signs, right by the leaning tower.
  • Visit the Baptistery: I didn’t enter, but pictures do look very pretty! This alone will set you back €5, or you can pay €7 or €8 for a two or three-monument combo, respectively. See the official website to understand!
  • Chiesa di Santa Maria della Spina: I actually know nothing interesting about this church, but I think it looks super cool. Try to walk by it by using Ponte Solferino bridge on your way back to the train.

Also, Pisa is a really pretty Tuscan city! So there’s absolutely no harm in sticking around longer and actually seeing the city of Pisa. You can just budget extra time to walk around before heading back on the train, or even stop for a meal.

Cinque Terre

Cinque Terre translates literally into the “five lands” in Italian, representing the five villages that make it up. The villages are Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. I highly recommend not choosing Corniglia as a base, only because there is a 350+ step staircase from its train station to the actual village. (Psst: Check out my guide on alternative, cheaper Cinque Terre bases.)

Riomaggiore at sunset in Cinque Terre

How to Get to Cinque Terre from Pisa

Take a regional train from Pisa Centrale train station to your preferred Cinque Terre village of choice. All journeys will require a train transfer at La Spezia Cenrale station. You might consider using La Spezia as your base, since it might be cheaper, saves some train hassle, and is included in the Cinque Terre Rail Pass (more on the pass later on – don’t worry!). Train times and prices are below.

  • Pisa to La Spezia: 75 minutes and €7.90
  • Pisa to Riomaggiore (the southern-most village): 1.5 – 2 hours, because it requires a transfer at La Spezia, and €8.60
  • Pisa to Monterosso (the northern-most village): 1.5 – 2 hours, because it requires a transfer at La Spezia, and €8.60

What to Do in Cinque Terre (One & a Half days)

The main things to do in Cinque Terre are visit all five villages and hike between them. Unfortunately, more than half of the famous trail is closed for reconstruction after an avalanche. Currently, the only open part of this specific trail is from Monterosso to Vernazza and from Vernazza to Corniglia, but you can check here for updates.

To hike it, you’ll need to pay (unless it’s winter when there’s apparently no one checking). For this itinerary, get the two-day €23 trails and train card. This grants you unlimited access to the paid trails and unlimited train travel between Levanto and La Spezia. It also allows you free public toilet usage in the villages and free WiFi at the village train stations. You can buy in person at any train station or information desk.

Besides the hikes, there is no real to-do list of attractions for each village, so just stroll around at your leisure, swim when you feel like it, and enjoy the beauty! If you’re looking to get off the beaten path (literally), I wrote about the free Cinque Terre hikes you can do instead of the paid ones. The views are better, too, in my opinion!

Day One (Half Day)

Riomaggiore and Manarola: After settling in from Pisa, I recommend splitting the remainder of this day relaxing and hanging out in Riomaggiore and Manarola. Try to be in Manarola for sunset, to get that cliché Instagram view. That café you see everyone take their pics at? It’s called Nessun Dorma.

Day Two

Hike Monterosso to Vernazza to Corniglia: Finish up the last three villages, and get some hiking in! You can do the hike either direction you please. I highly recommend hiking with your swimsuit underneath, because there is nothing you’ll want to do more after a hike, than jump into that water!

What to Eat in the Cinque Terre

These are some yummy traditional foods to try while exploring the Cinque Terre.

  • Pesto alla Genovese: This beloved pasta sauce made from crushed garlic, pine nuts, salt, basil leaves, olive oil, and cheese hails from the region of Liguria (the region where the Cinque Terre are located). More specifically, it comes from Genoa, as the name implies. But anywhere in Liguria is an authentic place to try a pesto dish!
  • Focaccia: A warm slice of this fluffy, oily goodness makes for the perfect snack while zipping from village to village, or even a quick breakfast alongside some coffee before heading out for the day. It is made from flour, water, olive oil, salt, and rosemary, so it’s a great option for vegans as well.
  • Farinata: Another delicious vegan food to try, farinata is a flat pancake-or-crepe-like food made from chickpea flour. You can pick up a slice as a snack on the go.
  • White wine: Especially if you hike the trails between the Cinque Terre, you’ll notice a lot of white grape vineyards scaling the cliffs of this area. So it’s no surprise Liguria is known for its white wines!


I was worried before getting to Venice that I would hate it. So many people complain about its crowds, its mosquitos, its flooding… The list of negatives seems endless! But after just my first hours in Venice, I really felt like people give it a bad rep. Yes it is way too crowded in the center. But honestly, the crowds are completely justified.

I would describe Venice as: so beautiful, it’s unreal. And can you really blame crowds for flocking to something like that? Try to knock out all the main sights at less-crowded hours. Then spend the middle of the day exploring the rest of the city, where it’s much, much less crowded, but just as beautiful. Do that, and you might just end up liking it!

Grand Canal in Venice from Acadamia Bridge during sunset

How to Get to Venice from Cinque Terre

OK…get ready for a lot of patience today! Getting to Venice involves two transfers and 4 hours of train travel. And if you stayed in Cinque Terre proper, add one more transfer in La Spezia. But it will be worth it!! Plus, I’ve done all the planning headache for you. *wink, wink, nudge, nudge*

From La Spezia Centrale, transfer at Pisa Centrale to Firenze S. M. Novella. Then from Firenze S. M. Novella, it’s a direct, 2.5 hour shot to Venezia S. Lucia. Because the journey is so long, you’ll need to take two Frecciarosa trains (those less-expensive-the-further-out-you-buy-ones). If you purchase last minute, this entire trip will cost €81. But if you buy two-ish months out, it’ll be closer to €55. Of course, you could take slower trains to save money, but you’d need more transfers, and who wants to be in a train more than 4 hours anyways?!

Once in Venice, you’ll want a vaporetto pass. Trust me – you don’t want to be lugging bags up and down those bridges! If you are 29 years-old or under, I highly recommend buying the Rolling Venice Pass. I wish I knew about it earlier! It costs €6, but in order to buy it, you must also purchase (at minimum) an unlimited three-day vaporetto pass for €22. With the pass, you also get discounts on many attractions, like a €12 discount entrance to the Doge’s Palace! The one-day transport pass alone costs €20, and the two-day pass costs €30, so getting the Rolling Pass quickly pays for itself. You can buy these passes online or in person once in Venice.

What to Do in Venice (Two Days)

Assuming you take the first reasonably-timed morning train from Cinque Terre, you’ll get to Venice sometime around noon or 1pm. Add some time for navigating the canals to locate your accommodation, and you basically have 1.5 days in Venice. (If that sounds like too little, you can remove the Burano and Murano day trip from the suggested itinerary below. But honestly, you’ll be fine!) If you want a more detailed walkthrough plus photographs of each of the below, check out my article on best things to do in Venice.

Day One

  • Piazza San Marco: This main square is where most of the (tourist) action is. Firstly, there’s the Basilica San Marco. It’s free to enter, but there can be a very long line most hours of the day, so be careful what time you go. I went in the middle of the day when I saw it was shorter, and was in and out in 10 minutes! If you’d rather not risk it, you can book your time slot online during high season for a €2 booking fee. Large bags are not allowed inside, but there’s a free luggage storage the basilica will tell you to use. Across from the basilica is the Campanile (the bell tower). You can take the elevator up it for €8. If you want to skip the line, it’s the same website as the basilica. There’s also the Doge’s Palace. Entry is €25, but only €13 with the 29-year-old Venice Rolling Card I mentioned above. See the official site for more deets.
  • Bridge of Sighs: Walk around the Doge’s Palace, making a left turn around the corner along the water. From the first bridge, you’ll see the famous Bridge of Sighs. It’s named so because it connects to the prisons, and prisoners sighed while taking one last look over beautiful Venice as they walked through the bridge to their dooms.
  • Rialto Bridge: If you haven’t figured out by now, Venice has a lot of cool bridges!
  • Accademia Bridge: This was my favorite bridge, because it has such an amazing view.

Day Two

  • Take a half-day trip to Burano and Murano: Honestly, I did find this a little overrated, but maybe I’m just bitter because I got bad weather? I have an in-depth guide on how to visit the islands from Venice, as well as what each island is all about.
  • Fondaco dei Tedeschi: This shopping center has free rooftop views of Venice, but you’ll need to book in advance (I recommend at least a day or two prior to get your ideal time slot). It’s located right at the edge of the Rialto Bridge on Calle del Fontego.
  • The Grand Canal: The obvious way to float around Venice is on a Gondola. This will set you back €80 per gondola (six people max) in the daytime, or €100 sunset and later. Prices are fixed, so check current gondola prices, and don’t let anyone overcharge you. Alternatively, you can ride the vaporetto between San Marco and the train station, which is free since the vaporetto pass for the Burano and Murano day trip is still valid! I reeeeally recommend timing this during sunset. It’s SO pretty (and a lot less hectic).

What to Eat in Venice

These are some Italian favorites to try that come right from either Venice itself or the Veneto region.

  • Tiramisu: This beloved Italian dessert made from coffee-dipped ladyfingers, whip, sugar, mascarpone cheese, and cocoa is not from Venice itself, but rather from the nearby city of Treviso to its north. Nevertheless, anywhere in the region of Veneto is an “authentic” place to try this yummy sweet.
  • Risotto al nero di seppia: Some may find the black color intriguing, while others may find it offputting. Either way, squid ink risotto is a must try while in Venice!
  • Aperol Spritz: Also called a Spritz Veneziano, you’re sure to spot this bright orange drink all throughout your two week Italy vacation. But this cocktail made from prosecco wine, Aperol, and soda water was actually invented in the Veneto region.
  • Belini: Another famous Italian cocktail invented in Veneto – but this time from the exact city of Venice itself. In fact, you can have it right in the very bar where it was invented, Harry’s Bar, in San Marco Square. (But be warned – this is a very expensive way to have it if you sit down at one of the tables there!) This cocktail is made with Prosecco wine and peach purée or nectar.
  • NOT PIZZA: If you are looking for an “authentic” Italian pizza, Venice is not the place to have it. As I mentioned above when explaining where you should try authentic pizza (Naples), pizza as it was first invented must be made in a wood burning oven. And Venice has none! Venice is built out of wood, and apparently wood burning ovens were banned after a pretty bad fire in the past. So if you fancy a pizza while in Venice, that’s fine, but know that it’s very far from “authentic” pizza!


Milan is known as fashion capital of Italy…and honestly not much else! It’s a city many aren’t enthused by, and I wouldn’t recommend it if you only have one week in Italy. But for a two week Italy itinerary, I really do think it’s appropriate. It’s home to the world-famous Last Supper painting, an iconic Duomo…and not a whole lot else! Which, in my opinion, makes the perfect, not-too-hectic final stop on your epic, two week tour di Italia.

Milan Duomo Cathedral

How to Get to Milan from Venice

Take a train from Venezia Santa Lucia to Milano Centrale. I recommend taking the direct, 2.5 hour Frecciarosssa train if you book far out enough, when it’s €28.90 for the morning train. If you buy closer to departure date, it’ll be €49. Otherwise, the regional train is €20.70, and the transfer in Verona only adds an hour more to your journey.

What to Do in Milan (One Day)

  • See the Last Supper: Book this is as soon as you can! Tickets to see Leonardo Da Vini’s masterpiece are available on the official site three-ish months in advance. They cost €15, plus a €2 online fee, and allow you a 15-minute viewing of the famous painting in the Santa Maria delle Grazie church. On the first Sunday of every month, tickets are free, so all you would pay is the online booking fee. Unfortunately, official tickets tend to get scooped up on the first day they’re available by tour operators. So if you don’t get a ticket yourself, the only other way is to book a guided tour. These run for around €40 and above.
  • Go to the Roof of the Duomo: Entrance to the roof costs €10, to the church interior costs €3, and the online booking fee on the official site is €1.50.
  • Galleria Vittorio Emanuele II: It’s to the left of the Duomo, and it’s just way too glamorous not to walk through! It’s also Italy’s oldest active shopping gallery. If you fancy a rooftop view of the Duomo, apparently you can take a €12 elevator up to the top.
  • Navigli Lombardi: This area of a couple canals is super cute to walk around or eat in the evening!
  • Starbucks Reserve Roastery: I’m not even a coffee fanatic, but I just had to pop my head into the first Starbucks in Italy. Definitely the bougiest Starbucks I’ve ever seen.

What to Eat in Milan

  • Risotto alla Milanese: No trip to Milan is complete without trying this famous dish! Its yellow color comes from the saffron used, which just so happens to be the world’s most expensive spice – more expensive than gold.
  • Cotoletta alla Milanese: This veal cutlet is similar to the Wiener Schnitzel you might be familiar with from Austria, but it is cooked and served with the bone in.
  • Panettone: This world-famous Italian sweet bread dotted with candied fruits and raisins hails from the city of Milan. It is especially popular during Christmas and New Years.

How to Get Out of Milan

Alas, your epic two week Italy trip has come to an end! You’ll need to get out of Milan. Milan’s international airport is Milan Malpensa (MXP). There are a couple ways you can get from Milan’s city center to MXP.

  • Option 1: By train. From Milano Centrale train station, take the Malpensa Express train to the airport for €13. The ride takes an hour. Or, from Milano Cadorna train station, take the Malpensa Express train to the airport, still for €13. The ride takes 45 minutes. Purchase tickets in person at train station kiosks or online.
  • Option 2: By taxi. The fare for this 50 minute ride is fixed at €95. Make sure you get into an official taxi. They should accept card, and you can double check this as well as fare before getting in.

Adjustments to this 14 Day Italy Itinerary

  • Starting in Milan instead of Rome: You can totally do this two week itinerary in reverse order. However, when you get to Florence and head to the Amalfi Coast, keep the Amalfi Coast portion in the same order. That is, still start at Pompeii and end in Capri. Then, head from Capri to Rome to end the trip.
  • Flying in or out of Venice instead of Milan: Venice and Milan can easily be reversed in the itinerary, in case you find a good Venice flight. You’ll just train between Milan and the Cinque Terre instead of Venice and the Cinque Terre.
  • Visiting Siena instead of Milan: If you already know you have no interest in Milan, consider replacing that day with adding an extra night in Florence. From there, you can make an easy day trip into Siena (or any other town in Tuscany!).
  • Visiting Lake Como from Milan: If you can add just one extra night in Milan to this fourteen day Italy itinerary, you can squeeze in a lovely day trip to Lake Como from Milan. I detail exactly how to do it without a tour group and on a budget here.
  • Skipping Capri if it seems too hectic: If the half-day in Capri and evening train to Florence sounds too hectic, I don’t blame you. It might be more enjoyable to save Capri for a return trip to Italy. Use the extra day as another day in either the Amalfi Coast, or add an extra night in Florence or Milan for one of the day trips I mention above.

Any Questions on These 2 Weeks in Italy?

I know that was A LOT! If you’re planning your own two week itinerary for Italy soon and want some personalized advice, drop a comment below with your questions. Whether it’s a two week Italy honeymoon or you’re backpacking Italy two weeks, I love playing travel agent for people!

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Planning a trip to Italy soon? This two week itinerary for Italy has you covered! This travel guide has all the main things to do in Italy, like Rome, Venice, and Florence. It's also got coastal gems like Cinque Terre and the Amalfi Coast.
Planning a trip to Italy soon? This two week itinerary for Italy has you covered! This travel guide has all the main things to do in Italy, like Rome, Venice, and Florence. It's also got coastal gems like Cinque Terre and the Amalfi Coast.
Planning a trip to Italy soon? This two week itinerary for Italy has you covered! This travel guide has all the main things to do in Italy, like Rome, Venice, and Florence. It's also got coastal gems like Cinque Terre and the Amalfi Coast.


  • Jessica Cloutier
    January 30, 2024 at 8:19 PM

    Hi there,

    Thank you so much for all the valuable information! We’re doing a bit of a shorter trip as we are staying a few days in Paris as well as Switzerland. We plan to have 11 -12 days in Italy. I am wondering how you would reconfigure the itinerary. I have been to Italy on a school trip and was planning on skipping Rome this time around (been to Florence as well but would like to go back). I also wanted to check out lake como. Any suggestions are greatly appreciated.

    • That Travelista
      February 5, 2024 at 8:26 AM

      Hi Jessica,

      I’m glad the information is helpful!

      Since the itinerary is 14 days and the Rome portion is 3 days, I would just remove those 3 days and have an 11 day itinerary. That would have you starting in Naples (which has an airport) and ending in Milan, or the reverse – whichever works out better for you.

      If you want to see Lake Como on a day trip, it’s possible and would keep the itinerary within 12 days. I detail how in my Lake Como day trip itinerary from Milan. If you want to overnight in Lake Como, I would cut some days out from whatever interests you least and tack on those days to Lake Como. Maybe the half day in Capri because it’s a little complicated, or maybe Milan because it’s not as beloved, or maybe a night from Florence since it’s a repeat for you, etc.

      I hope that helps!!

      – Em

  • Ken
    January 12, 2023 at 7:42 AM

    This post is amazing! Would love your input on 14 days flights to and from FCO – Rome (Wednesday arrive, Tuesday depart). We hope to hit Rome, Pescara, Roccamorice, Naples, Pompeii, Sorento, Pompeii, Amalfi, the hike you mention, and maybe Capri. We dont mind paying for some accommodations, but we also have a friend in Naples where we can stay for free. Any tips on itinerary and how to get around?

    • That Travelista
      January 12, 2023 at 9:38 PM

      Hi Ken! I’m so glad to know the post was helpful! 🙂

      That’s so awesome you have free housing in Naples!

      The bulk of everything you listed is day-trip-able from Naples – just Rome, Pescara, and Roccamorice aren’t. I haven’t been to Pescara or Roccamorice, but based off a quick Google Maps search of public transport, it seems there are trains and buses between Rome and Pescara. It seems that there is a long (5hr) Flixbus between Naples and Pescara, but that a train trip between the two has to transfer at Rome. I didn’t see any way to get to Roccamorice with public transport from Pescara, Rome, or Naples.

      Off the top of my head, I would say to combine Rome, Pescara, and Roccamorice as one leg of the trip. Let’s call it Leg A.

      Leg A:
      Day 1: land in Rome, explore if you have time/energy, sleep in Rome
      Day 2: Rome, sleep in Rome
      Day 3: Rome, sleep in Rome
      Day 4: travel (probably train) to Pescara, explore, sleep in Pescara
      Day 5: day trip to Roccamorice (I imagine there must be some way to get there by local bus? I’d look more into that!), sleep in Pescara
      Day 6: travel to Rome (or to Naples by Flixbus, depending on the day)

      Sorrento, Pompeii, a hike up Mt Vesuvius (if that interests you), and Capri are all super-duper easy day trips from Naples. So, if you’re wanting to save budget, I’d plan all those as day trips (and maybe overnight in Capri if you want, to experience it without the day-trippers) from your friend’s place. And Naples itself also has things to see!

      I think it’s worth spending a night or two in either Positano or Amalfi to spend one day in each and do the Walk of the Gods hike. But you technicallyyy can day trip to them from Naples as well. If you do, I’d recommend by ferry, because doing the train from Naples to Sorrento, then the bus from Sorrento to Positano/Amalfi, and then returning…all in the same day…multiples days…just sounds terrible to me! But the ferry would be €30 – €40 ish round trip each time, so multiply that by multiple people and two or three days, and I feel like you can just put some of that money towards accommodation instead, spending more time exploring and less time commuting!

      Either way, I’d say to combine Naples, Pompeii, Sorrento, Positano, Amalfi, the hike, and Capri into another leg of the trip. Let’s call this next bit of the trip Leg B.

      Leg B:
      Day 1: travel to Naples from Rome by train (or from Pescara by Flixbus), explore depending on time, sleep at friend’s place
      Day 2: day trip to Pompeii + Sorrento, sleep at friend’s place
      Day 3: travel to Positano in morning (probably ferry), explore, sleep in Positano (or Amalfi if you decide)
      Day 4: take bus/cab to Amalfi, explore, take bus/cab to start of hike, hike to Positano, sleep in Positano (or rearrange this if you decided Amalfi for Day 3)
      Day 5: take ferry to Capri, explore, take ferry to Naples, sleep at friend’s place (or overnight in Capri, taking ferry to Naples the next day)

      So all that puts you at about 10 – 13 days, depending on if you add extra nights to Capri or the Amalfi Coast or Naples, and whether you combine day 6 of Leg A with Day 1 of Leg B.

      If you have an extra 2 – 4 days, you can add a Leg C of Naples/Rome-Florence-(+ Pisa if you want)-Rome, or Naples/Rome-Florence-Venice-Rome, or Naples/Rome-Venice-Rome, etc. by fast train. Know that Venice is going to be a long train ride from Naples, though!

      And you can rearrange any of the Legs A – C into whatever order fits best with your flights or your friends’ schedule, etc. since Rome is kind of the focal point of them all.

      Hope some of that is helpful!! I think it all depends on how much you care to “fit everything in!” If that’s not a concern and you can return to Italy later on to tour the north, I’d say spending all 14 days in the areas you listed and taking it more slowly sounds the most enjoyable! (Renting a car is also an option, but as I’ve never done that in Italy and my itinerary was all public transport, I’ve stuck to public transport in this response.)

      I’m sure you’ll love your trip whatever you decide. 🙂

  • Ruth
    April 20, 2022 at 9:29 AM

    Hi there!

    Is it best to book the air first and then find the accommodations? I’m wanting to go to Italy this May…in a few weeks.

    • That Travelista
      April 20, 2022 at 9:56 AM

      Hi Ruth! Italy in May sounds like the perfect time!

      I’m a huge planner, so I like to plan a rough itinerary (which includes looking at any train schedules/prices, skimming housing options, flight options, etc.) before booking anything.

      Sometimes I book free-cancelation accommodation first before booking my flight/transport. But if I am staying in an Airbnb or something not fully-refundable, or if the flight price is very good, then I tend to book the flight before the accommodation. So there really is no correct order! 🙂

      But since your trip is coming up soon, maybe it’d be a good idea to at least look at accommodation first to make sure there are enough options for your destination within your budget before you put down money on a flight.

      Hope that helps!

      • disfruta2vidagmailcom
        April 29, 2022 at 12:24 PM

        So, I’ve decided to change my trip to 21 day in and out of Milan…how would you restructure the itinerary?

        • That Travelista
          April 29, 2022 at 1:15 PM

          How exciting!

          With seven extra days I would use one day to travel back to Milan from Rome at the end of the trip (Roma Termini to Milano Centrale, fast train takes 3 hrs) and for the remaining six days, choose what interests you the most from the below options:

          – one extra night in Milan to do a day trip to Lake Como (or spend a couple nights on Lake Como)
          – one extra night in Milan or Venice to do a day trip to Verona (or spend one night in Verona in between traveling between Milan and Venice, or spend two nights in Verona to see Verona one day and day trip to Sirmione on Lake Garda the second day – I meant to go to Sirmione from Verona myself but didn’t because of rain)
          – one or two extra nights in Cinque Terre to rush less or do a day trip to Portofino (this guide is from Genoa but is just as doable from Cinque Terre) and/or Portovenere
          – one extra night in Florence to do a day trip to Siena
          – one extra night in Florence to do some sort of organized day trip that includes Val d’Orcia and/or Tuscan countryside wine tour (I haven’t done either of these)
          – one extra night in Florence to do a day trip to San Gimignano (I haven’t been but have heard nice things)
          – one extra night in Amalfi Coast to rush less (and/or add a night to Capri to spend a full day there and not just a few hours)
          – a couple nights in the Emilia Romagna region (in between Venice and Florence – main city is Bologna) I only recommend this if you love the food from here (bolognese sauce, parmesan cheese, prosciutto di parma, and balsamic vinegar are a few famous ones) and plan to do food tours, as it’s known as a foodie haven

          The above options allow you to stay in the same area and get to know it better/less rushed. But you could also add an entirely different region to your trip if that is what you prefer. You could rent a car and explore the Dolomites in the north, you could travel alllll the way south and see some of Sicily or Puglia (but that would be a very long travel day back to Milan or require a domestic flight), you could spend time on the island of Sardinia, etc. I haven’t done any of these things (yet!) so I can’t give much advice on them. If it were me, I would stick to the first options I listed and save further-away things for return trips to Italy. 🙂

          Hope some of that helps!! 🙂

  • Stephanie
    April 15, 2022 at 7:52 PM

    I have a 2 week vacation coming up in May and I’m thinking about going to Italy but have to idea how to plan it; where to go or where to stay!

    • That Travelista
      April 18, 2022 at 10:26 AM

      Hi Stephanie! How exciting! I think May is a perfect time to see Italy (that and September) because the weather is warm but it’s not high season. You’re going to have an amazing time. 🙂

      If it were me and my first time in Italy, I would follow this two week itinerary exactly as I have it laid out. I like to maximize places I’m seeing while still having enough time to “see everything” in each place, and the itinerary as I have it laid out does that. It hits the three main, can’t-miss Italy destinations (Rome, Venice, and Florence) plus fits in the next tier of popular destinations (Cinque Terre, Pisa, Milan, Amalfi Coast/Capri, and Pompeii).

      The only additional planning you would need to do is your accommodation. I like to use because I like its interface and app, that many properties listed allow free cancelation, and that it lists hostels (I’m not doing hostels at the moment though, due to the virus). But other sites you can use include, Airbnb, or HostelWorld. It depends on your budget and style. 🙂 Also, I always check the walking distance from the train station to the accommodation on Google Maps before I book.

      If the itinerary as I have it laid out seems too jam-packed for you and you like to travel slower, you can let me know what you’re looking for (beaches/relaxing, focusing on one region and returning to the country later for other regions, art/history/museums), and I can give my thoughts on what to add and take out! 🙂

  • Karan Sachan
    March 18, 2022 at 10:25 PM

    My wife & I are heading to our 2 weeks Italy adventure next week. After Rome, we were thinking of renting a car until the end. Do you know what is the parking situation? Would hotels/airbnbs provide accessible parking options overnight? Is parking fare like insane expensive?

    • That Travelista
      March 19, 2022 at 8:32 AM

      Hi Karan! How exciting!!

      I’ve never driven a car in Italy, so I can’t say much from personal experience. But the answer depends on what places you are visiting. 🙂 If you are seeing just the places on this itinerary, for me, a car isn’t worth the hassle because it’s so easy to travel between the main tourist destinations by train. The only parts of this itinerary that I think could be easier to get to with a car would be Positano and Amalfi, so just 2 out of 14 days. But maybe you will be exploring smaller towns of the Tuscan countryside, or heading to Sicily, or something like that, which then would have a different (easier) parking situation than the major tourist cities/spots! So the answer depends a lot on your specific itinerary.

      Airbnbs sometimes do have parking and they list it on their Airbnb page if they do. Same with hotels. But if it’s not listed on their page, I wouldn’t expect parking. In my experience driving in other European cities, parking is expensive, but like I said, I can’t speak from experience on Italy.

      If you do go with a car because you prefer to not be on a train schedule, I would suggest to plan where you will be parking in advance (Google search or see what others on TripAdvisor have shared). You might be able to find the costs in advance and then decide for yourself if it is too expensive vs the trains or worth it. 🙂

      I hope some of that helps!

  • Kam Prasad
    March 16, 2022 at 9:14 AM

    My wife and I are planning a trip to Italy in late May. Your itinerary has been of great help in coming up with our plan – thanks very much for taking the time to write such a detailed travel plan. The following is our draft itinerary:

    17-Mar Arrive Milan 2:30 PM
    18-Mar Milan sightseeing
    19-Mar Lake Como
    20-Mar Morning train to Venice
    21-Mar Venice, Train to Florence in the evening
    22-Mar Florence
    23-Mar Florence, Pick up rental car drive to Tuscany in the afternoon
    24-Mar Tuscany (includes Pisa and Cinque Terre among other places)
    25-Mar Tuscany
    26-Mar Tuscany
    27-Mar Drive back to Florence, drop rental car, take train to Rome
    28-Mar Rome
    29-Mar Rome
    30-Mar Vatican
    31-Mar Train back to Milan, flight out at 2 PM

    We will be meeting my sister and brother-in-law in Florence and will be with them for the Florence and Tuscany leg of the trip. The dates and days for this leg of the trip are kind of fixed so we are going with their plan and will be sharing the AirBnB they booked in Tuscany. We intend to cover Pisa and Cinque Terre while we are there. We intend to rent a car to drive to Tuscany, only place on this trip where we plan to do that.

    Initially I had Amalfi Coast in there but reading your comments, I took that out for a later trip that could combine that and potentially Sicily (always wanted to visit Palermo/Bagheria – The Godfather effect!).

    Would appreciate your insights on the overall itinerary. A couple of doubts that we have are are we budgeting too little time in Venice and is 3 days too much for Rome/Vatican? Thanks a lot in advance.

    • That Travelista
      March 18, 2022 at 9:49 AM

      Hi Kam! I’m so glad to know my post and comments have been helpful to you. 🙂

      What you have looks like an awesome itinerary! You are going to have a great time leaving it just as is. Personally, I liked Rome most between Rome/Venice/Florence, so I may be a little biased in saying that 3 days would never be “too much” for Rome. 🙂 That being said, my own itinerary only allots 2.5 days to Rome, so if you wanted to arrive in Rome one day later so that you take the train from Florence the following morning, arrive in Rome by or even past noon, and have 2.5 days instead of 3, I think you can still see everything in Rome that you would have seen. That would allow you to either have more time in Florence or maybe arrive in Florence from Venice the next morning and have one more night in Venice. (Not sure if that part is already fixed though?)

      I think, make your decision on what interests you and your wife most between ancient history (Rome), renaissance art (Florence), and a visually stunning city (Venice). I think you’ll be able to “see everything” in Venice with your current itinerary because it’s a pretty small place, especially the touristic center. So the decision is more if you think you want to “hang out” longer in a visually pleasing city rather than about if you will miss seeing something touristic. As for the Vatican, some people allot a whole day to it. Others half a day. (This also depends on if you are buying skip-the-line tickets in advance.) I personally am not interested enough to spend more than half a day (I love Rome’s ancient Rome stuff more than the Vatican stuff), but maybe you and your wife love art and museums more than I do. 🙂

      So to answer your question, I think the itinerary as you have it looks good and you’ll “see everything.” But if you are nervous, I think you can remove 0.5 days from Rome and add it elsewhere without seeing any less of touristic Rome. And I think Amalfi + Sicily for a future trip sounds like a dream!

      • Kam Prasad
        March 20, 2022 at 10:51 PM

        Many thanks for taking the time for writing a detailed reply and apologies for my late response. We have made one change to our original plan: the more Youtube videos I saw of the Amalfi coast the more it felt like we should get at least a glimpse of it on this trip. So I have gone in the opposite direction and added one more night to Rome (stealing a day from Tuscany)!. In addition to giving more time for the historical sites, we plan to do a quick day trip of the Amalfi run by Walk Tours of Italy which should gives us a glimpse of its wonder and hopefully tempt us for a return trip! Once again many thanks for your help and all the best.

        • That Travelista
          March 21, 2022 at 1:01 PM

          An organized day trip is a great way to quickly see the Amalfi Coast from Rome! It’s very stunning/unreal place, and I know you’ll love it! I would love to know how the whole trip went after you return. 🙂 Have the best time!!

          • Anonymous
            March 22, 2022 at 11:40 PM

            Thanks for your help again and will be sure to write after we return from the trip.

  • Anonymous
    October 23, 2021 at 4:09 PM

    We are planning on arriving in Naples March 26th or so and want to spend two weeks in Italy. Our final destination will be Marseilles France. We will arrive in Naples from Sicily.
    What do you recommend for an itinerary for those 2 weeks.

    • That Travelista
      October 25, 2021 at 5:08 AM

      Hello! I’d recommend this exact itinerary, just in a different order. Since you are arriving in Naples instead of Rome, that’s actually less backtracking. 🙂

      I’d say to start with the Pompeii/Amalfi Coast/Capri leg. If you wanted to be based in Naples, it is technically possible to do Positano, Amalfi, Capri, and of course Pompeii each as day trips from Naples. So you would either rent a car, join tour groups, hire a driver, or DIY it by using the buses/ferries I mention. It would just be more time in transit each day vs being based in, for example, Sorrento.

      After that, I would take the train up to Rome and do the Rome portion of this itinerary. Then, from Rome take the train to Florence and continue with this itinerary exactly as is for Florence > Pisa/Cinque Terre > Venice > Milan. RyanAir has direct flights from “Milan” (the BGY airport in Bergamo, not the MXP airport) to Marseilles. But remember that they are a budget airline and very strict on baggage size/weight!

      Hope that helps! Feel free to respond back 🙂 Sounds like it will be such a lovely trip!!

  • Leslie
    August 11, 2021 at 9:26 AM

    Thank you for such GREAT information!!
    We plan to be in Italy in November…Hubby is teaching in Milan & Lithuania the first week of Nov & I will meet him in Rome when he’s finished. We should have 15 days, not including our travel days and I’m thinking Rome, Florence & Venice for sure. We like to be leisurely when we travel 😉
    Are there any of the destinations you listed that we should omit due to it being November?

    • That Travelista
      August 13, 2021 at 1:43 PM

      Hi Leslie! So glad you found the info useful 🙂

      As a Californian who’s pretty much only known the drought years, weather (including rain) really impacts where I want to travel! So keep in mind that bias in my response LOL.

      Like I mentioned towards the beginning of this post, Venice is prone to flooding during rain. So if it’s raining heavily there on your visit, it might not be enjoyable, but you won’t really know the forecast until closer to the date. I wouldn’t go as far as to say omit it, but just keep that in mind, and maybe you can pack or plan to purchase rain boots worst case.

      Personally my own interest in beach-y places (which in this itinerary would be Cinque Terre, Amalfi Coast area, and Capri) is entirely dependent on warm weather. So those would be the ones I personally omit and save for another visit. The order of omission for me would be: Capri, Amalfi Coast, Cinque Terre. Cinque Terre would be last to go for me because it’s all connected by train, so I imagine it would still be just as easy to visit. And apparently no one checks for the ticket to the paid hiking trail in winter, so assuming it is not rainy or just rained (muddy trail would not be fun) that might be a plus to going in winter. Amalfi Coast should still be doable, but I imagine the ferry schedules would be heavily reduced in low season, and potentially more canceled due to sea conditions, so getting to Capri might be annoying. All three of these destinations’ villages/towns are filled with souvenir shops, boutiques, and restaurants, so I would imagine some might be closed in winter, but not all.

      Since you like to be leisurely and the itinerary as I have it is very jam packed,
      * I would omit the entire Amalfi Coast and Capri leg of the itinerary. It’s a lot of moving around in a short time frame, and I don’t know that it’s worth it in cold weather. You can keep the Pompeii portion of the itinerary by just adding 1 more night in Rome and making Pompeii a day trip. So in the end, that would net save you 3 days.
      * I think Cinque Terre will be worth it if you just wanted to SEE the pretty towns (they’ll look exactly the same in winter as summer, and will be much less crowded!) but not worth it if you’d be very upset if the trails are closed do to mud from rain. If you omit this, that would save you 1.5 days. I’ll assume you don’t omit this for the following bullet.
      * With the 3 extra days, I would choose the 3 of the following that interest you most:
      ~ Day trip to Siena from Florence (add 1 night to Florence)
      ~ Day trip to San Gimignano from Florence (add 1 night to Florence) – I have not been, but have heard nice things
      ~ Day trip to Bologna from Florence or Milan (add 1 night to Florence or Milan) – I only recommend this if you love the food from here and plan to do a food tour, as it’s known as a foodie haven and is in the region where a LOT of the Italian dishes Americans love/know are from
      ~ Day trip to Verona from Venice or Milan (add 1 night to either Venice or Milan) – where Romeo and Juliet was set
      ~ If it happens to be a nice day, day trip from Milan to Lake Como (add 1 night to Milan)

      This would be a lot less moving around, so a lot more leisurely. If you want to save moving accommodation from Florence to Cinque Terre, you can also just do Cinque Terre as a day trip from Florence, especially if you do not plan to hike. I detail how I’d recommend fitting all villages (plus the main hikes) into one day here. This way, you would only be based in Rome, Venice, Florence, and Milan for the entire 2 weeks.

      Hope some of that helps! Feel free to respond back 🙂

      • Leslie
        August 18, 2021 at 6:08 AM

        Thank you, thank you, thank you! Your reply is very helpful 🙂
        We’re less about the beaches so omitting the Amalfi Coast & Capri makes sense. I hadn’t considered the Bologna region and that idea intrigues me as we do like food 😉
        Is it a crazy idea to think that we can plan just our Rome leg from the States & then figure out the rest while we’re over there, according to the weather forecast at the time? That would give us flexibility as to whether we begin or end in Venice before heading back to Rome for our flight home.
        Again, I appreciate all the time & effort you’ve put into your blog & responses!

        • That Travelista
          August 18, 2021 at 9:04 PM

          I don’t think that’s crazy at all! You will just have to pay some more for any long distance train tickets due to purchasing them closer to the date of travel vs weeks or months out (which I mention some price examples of in the post as well). November will be off season, and on top of that, we have the lovely pandemic which doesn’t seem to be going away any time soon, so I do imagine you would be able to get accommodation just fine.

          One thing I personally would do though is to still plan out what you want to do in each of the non-Rome legs of your trip in advance (at least roughly), and then just mix and match the order of the non-Rome legs later on. So plan what you want to do in Florence, how many nights there, roughly how to do any day trips from there, and then same for Venice and any other base cities, but then don’t book until getting to Rome if you like. That way, you don’t waste your vacation time in Rome searching the internet to plan time-consuming details. You can just spend a few minutes searching the weather, deciding the best order, and booking 🙂

          • Leslie
            August 19, 2021 at 8:59 AM

            Awesome, that’s good to hear. Thank you again!!

          • That Travelista
            August 19, 2021 at 11:39 AM

            You’re welcome! I’m sure you’ll love your trip 🙂

  • Ashley
    July 30, 2021 at 8:06 AM

    Hi, my husband and I are planning a 14-day honeymoon this October. I am worried we will spend most of our time on trains if we try to visit too many places. We fly in and out of Rome. Would you recommend skipping out on Amalfi Coast and heading north (Rome-Florence-Cinque Terre-Milan-Venice-Rome) instead? We don’t want to miss out on anything!

    • That Travelista
      July 30, 2021 at 5:35 PM

      Hi Ashley! I definitely understand that sentiment!

      If there was any portion of this itinerary to take out, in my opinion, the Amalfi Coast/Capri/Pompeii leg would be the one to go. The main reason for that is that it is a rather high ratio of travel time to non-travel time compared to the other legs of this itinerary, AND it easily could make up its own entire week+ Italy trip if you are able to return. A third reason would be that since you mention you don’t want to miss out anything, I think all the other destinations rank above Amalfi Coast/Capri/Pompeii in terms of what is considered most “must see.”

      So yes, what you said is what I would recommend. 🙂 Especially for a honeymoon, slowing down would be a lot more romantic!

  • Jennifer
    July 17, 2021 at 2:53 PM

    Hi, this itinerary sounds amazing. My husband and I would like to travel from the US to Italy for the first time next May. Do you have lodging accommodation recommendations and how to book them?

    • That Travelista
      July 17, 2021 at 6:53 PM

      Hi Jennifer! May is a lovely and comfortable time to travel to Italy. You will love it!

      I can’t say I have specific lodging recommendations for each destination, but I pretty much always use to look for and book my accommodation. I just really like the interface of their website for searching as well as how it lists your bookings out in chronological order, so it’s easy to keep track of where you are headed next. Plus, a lot of their listings offer free cancelation so that (1) I feel comfortable booking something earlier than I’m totally certain on it and (2) things are easy if plans change. And I find this to be true of both their desktop site and mobile app. They also have a large range, from five star hotels to hostels to guest homes, so I really like it as a one stop shop. (I’m not affiliated with them at all, they just happen to be the site that I almost always use for several years now.)

      One tip with them and with any hotel listing site is to check TripAdvisor after you have settled on the hotel but before you book. The photos on those booking sites are always provided by the hotel itself, so I often just do a quick skim of the traveler uploaded photos on TripAdvisor, especially if it is more of a budget accommodation.

      A lot of people of course love apartment rentals, so if you and your husband like that experience more, definitely look at AirBnB and Vrbo. I just personally prefer not having to coordinate check in and check out time with each host in an itinerary like this where you are moving around every few nights. I like that at hotels/hostels I can drop off my bag with reception if I arrive before check in or leave it there after check out if I’m sticking around. But the plus side is that you have the whole place to yourself, feel a bit more “like a local,” and can save money on food by grocery shopping and using the kitchen, packing lunches, etc. So kind of just depends on your style!

      I hope some of that helps! I just haven’t revisited each destination on this itinerary enough to try out enough different accommodations to be able to give strong recommendations 🙂

  • Anonymous
    April 28, 2021 at 9:42 AM

    This is the most amazing, detailed, helpful itinerary I have seen. Thank you for putting this together, it was SO helpful!

    • That Travelista
      May 3, 2021 at 10:40 PM

      Thank you so much for your kind feedback! 🙂 I’m glad to know it was helpful. I hope you love your time in Italy!

  • Jenny
    February 2, 2021 at 7:13 PM

    Hello there! Your itinerary is so helpful! My husband and I are a planning a hopeful trip to Italy this summer and since we are coming from the states we will have two less days than your itinerary permits. Do you have any advice when it comes to narrowing it down? Also, we are flying in and out of Rome. Thank you!!

    • That Travelista
      February 4, 2021 at 9:53 PM

      Hi Jenny! I’m so excited for your hopeful trip!!

      This itinerary is for 14 full days in Italy, so with two less days I understand you will have 12 full days instead. I would recommend you remove the Pompeii/Amalfi Coast/Capri and head straight from Rome to Florence instead.

      This is for three reasons:

      -Firstly, this part of the trip is the trickiest logistically (unless you hire a private car the whole way), so crowding it into the 14 day itinerary was already pushing it.

      -Secondly, this part of the trip is a little less “must-see” than the other destinations in my opinion. I define the “main” Italy spots as Rome, Florence, Venice, Milan, and in recent years, Cinque Terre.

      -Thirdly, this region would make/justify a nice one-week trip on a return visit to Italy.

      This would bring you down to 10 full days (which I happen to map out here: I would save one day as a travel day back to Rome at the end. That brings you to 11 full days.

      I would use the last full day as an extra night in either Cinque Terre, Florence, or Rome. I’d reco Cinque Terre so you don’t have to rush through it as quickly as I have in the itinerary. But you could also see more of Tuscany via a day trip from Florence if that region interests you more (Siena and San Gimignano are two popular ones, or perhaps a wine tasting excursion!). Or if you or your husband love the history of Pompeii, you can do a day trip there from Rome.

      Hope that helps! Feel free to respond back if any more questions/thoughts!

  • Rachel
    August 7, 2020 at 6:50 AM

    I can’t believe how detailed and helpful this is! I will definitely use this when my long-awaited trip happens. ❤️

    • That Travelista
      August 7, 2020 at 2:05 PM

      So glad to hear it’s helpful, Rachel 🙂 <3 I seriously wish I was (safely) traveling Italy right now! But at least we can plan now so everything's ready once we can go later 🙂

  • Sandra
    February 20, 2020 at 10:41 AM

    Since Italy is my “neighbour” country I’ve been there numerous times and visited majority of the places you included in the itinerary – and I must say you did a great job! Thorough & interesting – definitely super helpful for anybody who is planning their trip to Italy!

    • That Travelista
      February 20, 2020 at 5:44 PM

      Thanks so much, Sandra! Jealous that Italy is so close for you! 😉

  • Disha Smith
    February 20, 2020 at 12:42 AM

    You post has me missing Italy so much! I love how detailed you are in this itinerary. I definitely missed out on quite a few gems in Italy.

    • That Travelista
      February 20, 2020 at 5:44 PM


      The best part about missing something is it’s an excuse for a return trip 😉

  • Snazzytrips
    February 19, 2020 at 11:43 PM

    I love all the detail here. Will use this to plan my next trip to Italy. Amalfi Coast and Capri definitely on my list, including the Blue Grotto, but not sure now if I can do it.

    • That Travelista
      February 20, 2020 at 5:43 PM

      If Blue Grotto is top of your list, definitely don’t rule it out! Just budget enough time and skip out on some other Capri sights 🙂

  • Melissa Roos
    February 19, 2020 at 11:38 PM

    The detal in this post is amazing! I’ve been looking to visit Italy for a few days so these tips are very helpful.

    • That Travelista
      February 20, 2020 at 5:42 PM

      I hope you love your trip! I’m sure you will 🙂

  • Emma
    February 19, 2020 at 1:11 PM

    This is such a wonderful and detailed blog, so much useful info. And your photos are beautiful, thanks for sharing!

    • That Travelista
      February 20, 2020 at 5:41 PM

      Thanks, Emma! 🙂

  • Daniela Z
    February 19, 2020 at 1:47 AM

    wow!! the detail on this post is beautiful!! 🙂 this is inspiring me to go back to Italy ASAP 😀

    • That Travelista
      February 20, 2020 at 5:41 PM

      Thank you, Daniela!


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