Last Updated on July 7, 2024 by Tori’s VA
So, you’re going to Italy! I am so incredibly excited for you. You’re dreaming of pasta and gelato, the Tuscan countryside and zipping around Rome. But now it’s time to plan your 2 week Italy trip itinerary and you have no idea where to start. Or maybe you’re just looking to finalize the last details and timeline. Either way, I’m here to help!
My husband and I had a two week trip to Italy booked back in 2020 and, well, you know what happened. So since we had to push the trip pack a year and a half, that meant I was planning our extreme 2 week Italy trip itinerary for over two years! And let me tell you, I researched EVERYTHING!
And now I know that it was all worth it because I get to help YOU plan the perfect, most magical vacation to Italy with much, much less work. Follow my itinerary and you’re bound to have the best Italian adventure! Have so much fun! Andiamo! Let’s go!
This post may contain affiliate links for activities, destinations and products that I love, and think you will too!
How Long Do You Need in Italy?
There’s only one right answer here; as long as you possibly can. Seriously though, you should take as much time as you can afford to take for your vacation, because there is SO much to see here.
But for the average first trip to Italy I recommend at least 12-14 days. It allows you to visit several different towns and get a first taste of what the country has to offer. It by no means will allow you to see everything you want to see, but it’s a realistic start! And don’t worry…you’ll be back!
Where Should You Go in Italy?
There’s a million different ways that you could spend two weeks in Italy. What’s amazing about the country is how unique each city and village is, so there truly is something for everyone. So before you plan out your 2 week Italy Trip Itinerary, take into account what you enjoy and are looking for in a vacation. Ask yourself these questions:
Do I want to be busy every single day or do I want some time to relax?
Are there any sights that are a must-see, non-negotiable?
Do I want to spend most of my time in big cities or small towns?
What kind of Italian food do I want to try?
Would I like to visit places on the coast?
Do I want to go to lots of museums?
The best way to figure out the places that you want to visit most are by exploring blogs like this one and reading about each place and what it has to offer, and by watching YouTube videos of people in Italy. I love the series Adam and Kathryn from Adventures of A+K filmed during their two week Italy trip itinerary!
2 Week Italy Trip Itinerary Overview
For the first trip you take to Italy, I recommend staying in four places and seeing a variety of cities. This 2 week Italy trip itinerary will give you a great taste of the country and will leave you wanting to come back as soon as possible!
3 Days in Rome
3 Days in Tuscany
2 Days in Florence
2 Days in Venice
4 Days on the Amalfi Coast
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What are some other top destinations in Italy?
There’s endless beautiful cities and towns to see on your 2 week Italy trip itinerary, but here’s a few of the other top destinations you might want to consider:
Milan
Naples
Cinque Terre
Lake Como
Sicily
Sardinia
Matera
Dolomites
Genoa
Bologna
Parma
Verona
More Tips for Your 2 Week Italy Trip Itinerary
I have tons more tips for your 2 Week Italy Trip Itinerary, including how to get there, how to get around, how to find the best gelato and more! Skip to the bottom of the article to read all about those things if you want to! Or be sure to take a look at it after you read through the 2 week Italy itinerary! Grazie!
2 Week Italy Trip Itinerary Map
2 Week Italy Trip Itinerary
Okay it’s time to dive into the good stuff! Here’s how I would recommend anyone to spend their first 2 week Italy trip itinerary. Have so much fun!!
Day 1: Rome
I have a super-detailed guide to spending 3 days in Rome as well. The itinerary for that is slightly different because it assumes you have a full three days in the city, whereas here I also include the reality that you’ll be flying in and moving onto the next stop as well. They include almost the same exact activities, just in a slightly different order!
Landing and Getting to the City
You’ll likely land in Rome in the morning if you are coming straight from the US. After a long travel day, try to be as rested as possible to hit the ground running.
The airport is about 30 minutes away from downtown Rome, so you will have to decide how you want to get into downtown. You can either take a train or a taxi. I recommend a taxi, but I’ll explain both so that you know your options!
Train
Once you get through customs, look for signs that say “Train”. Yes, they will have English translations!! The signs are everywhere and are super straightforward. The walk is 14 minutes (I timed it) and is completely along an airport walkway and is super safe. You don’t have to fight any traffic or anything like that!
Once you arrive, you’ll see a few ticket machines that are self-service. It’s pretty simple to navigate, but there are also ticket windows if you prefer that!
Tickets to get from the Rome airport to Roma Termini (the central station in downtown) are currently €14 per person.
This is the only train that you will not buy tickets for in advance. That’s purely because you have no idea what time you will make it to the station after your flight. It could be delayed, there could be a long line for customs, or things could go super smoothly and you get there long before you expected! Also, these trains run continuously throughout the day so you’ll just buy a ticket at the machine and hop on the next train.
But PLEASE do not forget to validate your ticket before you get on!! There are little stamping machines that look like the photo shown above that you stamp it at before you get on the train. If you don’t then you could get fined!
I provide a lot more information about taking the train in Italy at the bottom of this article. It’s crucial to learn how to get around Italy by train so make sure you read to the bottom!!
Once you arrive at Roma Termini, you’ll then have to get to your accommodations. If they are close enough, you can walk. That’s what we did when we stayed at the St. Regis Rome. However, you’ll likely be too far for that, so walk right outside the train station and find the taxi stand. Taxis will be waiting for you and will take you straight to your hotel! It is typically about €10-12 depending on how far away it is.
Everything about taking the train was easy and safe, but I still prefer taking a cab. I’ll explain why below.
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Taxi
After getting through customs you’ll follow the signs for the Taxi station. Again, it’s very easy to navigate. Once you get there, you’ll see tons of taxis waiting in line. Jump in the first one in line and you will be on your way. The drive is only 30 minutes, so sit back and relax.
Taxis from the Rome airport to the Rome City Center have a fixed rate of €48. It doesn’t matter what hotel you are staying in, how many people, or how long it takes to get there.
I found taxis in Italy to be incredibly comfortable and safe. Everyone was super nice, most spoke very good English and they never tried to upcharge me or trick me. I absolutely recommend taking taxis in Italy!
So why do I think taking a taxi is the way to go? Because they take you directly from the airport to your accommodation. It will take much less time, and if you have several people in your group, then the price is pretty comparable! As soon as you have 3 or more people, it’s actually cheaper to just take a cab!
Check into Your Hotel and Rest
You’re probably exhausted after a long travel day (night?) and you need a nap. So check into your hotel and rest up for an hour or two! Need some hotel recommendations for Rome?
We stayed at the St. Regis Rome and our stay was incredible. The property is beautiful, the room was incredibly comfortable and luxurious and it was super close to the train station. However this hotel can be quite pricey and is a further walk from most of the sights.
We have also stayed at the Pantheon Iconic Rome Hotel, and WOW!! This hotel is incredible and my top recommendation for places to stay in Rome. The hotel is located directly next to the Pantheon and within walking distance to almost everything else. They have a beautiful rooftop bar, comfortable rooms and awesome staff. We love it there so much!
Get a Cappuccino
Once you’ve rested up a bit it’s time for you to get out and explore! You’ve been waiting for this moment for a long time. Get a cappuccino from the hotel or nearby bar (that’s what they call a cafe) to fuel you for the rest of the day.
Be sure to ask the barista for “Un cappuccino por favore!” This is one of my many tips I give in my article things to know about Rome.
Lunch at Roscioli Pasticceria
Walk to Roscioli Pasticceria (L’Antico Forno Roscioli) for lunch. Here you’ll find incredible Roman street pizza and other pastries to enjoy. But don’t eat too much, you’ll be taking a food tour in a few hours!
Jewish Ghetto Walking Tour
It’s time to start learning about this incredible city! You’ll already be close by, so start by taking the free audio tour of the Jewish Ghetto. It’s not super long but will take you around the area and teach you along the way!
Before you leave for Italy, make sure you download Rick Steves’ Audio Europe App, and download all of the tours you’ll need to your phone. And bring along some headphones and a portable battery pack to ensure your phone doesn’t die as you are out exploring each day!
Trastevere Walking Tour
Wander across the Tiber into the neighborhood of Trastevere. It’s one of the most local and authentic neighborhoods in Rome, since many locals live here! Take the Rick Steves walking tour of Trastevere next. If you want to go inside any of the beautiful churches in Trastevere, you will need to have your shoulders and knees covered! I recommend you bring a light shawl with you for this reason!
Trastevere Food Tour
It’s time to meet up with your tour group for a food tour of Trastevere! Since it’s where the locals live, it’s also where some of the best food in the whole city is! Book a food tour like this one in advance and you’ll get to taste authentic Roman cuisine from several different restaurants around the neighborhood. It will be one of the highlights of your trip, and a great way to get acquainted with the city’s food culture.
Walk Around Rome and Head to Bed
Most food tours end fairly early, around 6 or 7pm. So you’ll have some time to explore the city at night. If you didn’t get enough dessert on your food tour, head to Otaleg for gelato! Otherwise, explore the glowing cobblestone streets, people watch and enjoy your first night in the city. Head to bed and get a long night of sleep to be ready to explore more tomorrow on your 2 week Italy trip itinerary!
Day 2: Rome
Tour the Colosseum
Wake up early and start your day touring one of the seven wonders of the world, the Colosseum! You must make reservations in advance, and I highly recommend that you pick the very first slot available that morning. This place gets packed quickly, but when we visited at 9am, we had tons of space to ourselves to enjoy this gorgeous building. Just look at that photo of me roaming the halls; it looks like I own the place!!
The best option for visiting the colosseum is to take a guided tour. While not 100% necessary, you will learn SO much more this way and be able to appreciate what you are looking at. Otherwise, it’s kinda just an old building…
This Colosseum tour is a great option and one of the most inexpensive you’ll find. If you want to have an extra perk, book this Colosseum underground tour to see parts of the site that most don’t get to see.
If you decide that a tour is not for you, then be sure to buy tickets in advance directly through the colosseum’s website here. Be sure to download Rick Steves’ Colosseum audio guide if you go this route so you can at least learn a bit about the history. It’s a great alternative but not nearly as thorough or engaging as you will get on a tour. Any other “skip the line entry tickets” are a waste of money in my opinion because booking through the colosseum is also “skipping” the line when you arrive.
Explore the Roman Forum and Palatine Hill
Right next to the Colosseum is the Roman Forum and Palatine Hill. This is an area full of ancient ruins from the Roman Empire. This was the center of town for the people of the time and held all of the important buildings.
Today, you can wander around this massive area taking in the beauty and the history of the place. The tours I mentioned above will include a tour of this area, which is super important because it’s huge and there’s so much to learn!
I absolutely loved the Roman Forum; it’s gorgeous and in the spring was covered in wisteria, which made it that much more beautiful. Plus, the views you get from the Palatine Hill over the Forum and Colosseum are Christmas card worthy (you bet we used that pic on our Christmas cards! ha!) I wish we had more time here, but by this point we were STARVING! Let’s head to lunch!
Lunch at Pane e Salame
Now that you’ve worked up an appetite, walk a few minutes to Pane e Salame. It’s a small and casual lunch spot in the heart of Rome that mainly serves sandwiches and what us Americans call, charcuterie boards. YUM.
The food here is amazing and you get sooo much food for your money. Get a board, an Aperol Spritz, and relax for a bit to refuel for the afternoon.
Note: This spot only has a handful of tables and can get quite busy. So get here as early as you can to get a table or be prepared to wait a bit. But don’t worry, it’s so worth it!
Walking Tour of Rome
Grab your headphones and the Rick Steves Audio App and head to Campo de’ Fiori to start the Heart of Rome Walk. This is a really awesome tour that takes you to all of the top sights in Rome’s City Center. You’ll stop by Piazza Navona, the Pantheon, the Trevi Fountain, Spanish Steps and more! And learn about the city all along the way. I loved taking this “tour” and getting acquainted with the city!
Pantheon
As I mentioned, you’ll pass the Pantheon along the tour. Be prepared for your jaw to drop. The Pantheon is by far my favorite building in all of Rome and of my entire 2 week Italy trip as well!
Pause the tour, and get in line to go in. It costs €5 to enter, and you don’t need to make reservations in advance. The line will probably be pretty long at this point in the day, but don’t worry, it moves quickly.
As you wait in line, you’ll want to start the Rick Steves audio tour for the Pantheon! And remember, this is technically a church so have your shoulders and knees covered!
Granita de Cafe
Located just next to the Pantheon is La Casa del Caffè Tazza d’Oro. Stop here and grab a delicious Granita de Cafe. It’s basically a coffee slushie topped with whipped cream. YUM!
Continue with the Heart of Rome walk now that you have your sweet treat.
Siesta
After all of that exploring, I promise you will be wiped out. Head back to the hotel and enjoy an Italian artform, the siesta. They take a few hours each afternoon to rest. People go home from work for a bit, shops close and everyone pauses. I think it’s the perfect way to respect the culture and recharge for the evening. We love prioritizing siestas while on our 2 week Italy trip.
Aperitivo at The Court
Aperitivo is another important part of the Italian routine. It’s easiest to describe it as the Italian happy hour; a time for friends and family to come together after work and have a drink and light snacks.
But the ritual is also very much intended to prepare your stomach for the meal ahead. Certain drinks are most commonly drunk for this purpose including the Negroni and the Aperol Spritz.
You can enjoy Aperitivo all over town, but why not enjoy it looking over the Colosseum! Located on the rooftop of the Palazzo Manfredi hotel is The Court bar. It’s a gorgeous backdrop for a drink and some snacks. You’ll probably need someone to pinch you to believe it’s even real!
Reservations in advance are highly recommended. And be prepared, the drinks start at around €30 which is definitely pricey, but they do include a nice selection of finger foods to go with it. Makes the price not so hard to swallow!
Dinner at Roscioli’s Salumeria
You’re probably thinking, wait Tori, you just sent me here yesterday! But actually you were at the Pasticceria yesterday for lunch. Tonight you will be eating at the Roscioli Salumeria, right next door. It’s the sit down restaurant that serves super authentic Roman cuisine.
This spot comes highly recommended by alllll of the Roman food snobs including Katie Parla and Stanley Tucci. So we went, and they were right. It’s delicious!! The atmosphere is perfect and the service is very friendly.
Reservations are a necessity here so be sure to plan in advance.
Gelato at Fatamorgana Chiavari
Just around the corner sits this delicious gelato shop called Fatamorgana Chiavari that meets all of my qualifications for good gelato. See my tips section at the end to see what I mean. Grab some to go as you walk around the city for a bit.
Walk along the Lungotevere
If your 2 week Italy trip itinerary falls during the summer months, be sure to head over to the river and enjoy the Lungotevere. It’s a market that’s set up along the river each night in the summer with shopping, food, drinks and music! Spend whatever energy you have left at the market!
Day 3: Rome & Tuscany
Wake up early for photos at the Trevi Fountain
It’s time for the 6am wake up call. Plan to be at the Trevi Fountain this morning by 7am. You’ll be so glad I talked you into it when you see there’s only a handful of other people there and you can get pictures like I did. It looks like I’m the only one there admiring this epic piece of art. And of course, toss a coin using your right hand over your left shoulder to guarantee a return to Rome.
You’d better bet I threw my coin and plan to return many, many times!
Grab a Taxi (or Walk) to the Vatican
Next up, Vatican City! It’s the world’s smallest country yet there’s so much to see. So get over there early! You’ll start at the Vatican Museums; walking there will take about 45 minutes, so you might prefer to grab a taxi.
Either way, be sure to set the map to the Museums, because you’ll be about a 15 minute walk away if you just type in Vatican City.
Explore the Vatican Museums
Most people will choose to book a guided tour of the Vatican Museums. And for good reason! There’s SO much to see here and it can be very hard to digest it all without a guide. This tour of the Vatican Museums is a great option if that is what you are looking for.
However, this is another one of those times where I actually highly recommend using Rick Steves’ Audio tour. In fact, it’s the only one I think is really good inside a building or museum. The others can get kinda boring and unengaging, But this one was incredible. It was just the right amount of detail as we walked around the rooms of the museum and was so interesting!
If you decide to go that route, buy the tickets directly through the museum’s website. But whichever you decide, always book the earliest entry possible. This place becomes a madhouse very quickly each day, especially in the summer. And if that’s not enough to convince you, they also don’t have air conditioning. Do you want to be stuffed in there like sardines with some sweaty lady pressed up against you trying to get a view of the School of Athens? No thank you!
At the end of the museum you’ll get to see the Sistine Chapel, an insanely beautiful piece of art that is really incredible to see with your own eyes instead of in your 10th grade history book! But please respect the rules and don’t take any photos there. I promise the ones you can get on the internet are so much better anyways.
Wait in Line at St. Peter’s Basilica
After you are done at the museums, walk the 15 minutes around the city wall to the front of Vatican City. It’s here that you’ll see St. Peter’s Square, the entry to St. Peter’s Basilica. It’s free to visit which also means it’s a very popular spot.
Jump in the very likely long line to get in. When we were there in April the line was wrapped all the way around the massive square. It took us about an hour to get in. But while you wait you can take turns getting these awesome photos in between the columns in the square! If you had extra time before the museums then you should absolutely try to visit this first to avoid the line when it opens at 7am!
The Basilica is stunning, and feels like a million incredible works of art all around you. Look up, down, and side to side. There’s something everywhere you turn. And remember, you absolutely must have your shoulders and knees covered inside! So bring a light shawl with you!
Get Trapizzino for Lunch
It’s time to grab a quick lunch before you leave Rome. Quite possibly the BEST food I ate in all of Italy was the Trapizzini at Trapizzino. And that is a huge feat because the food I ate during my 2 week Italy trip itinerary was all so incredible. You must have it for lunch before you leave Rome.
They’re these pizza pockets filled to the brim with Italian foods like meatballs or chicken cacciatore. But the dough is so incredibly light and crispy and the sauces are thick and heavenly. Ugh, it’s the best.
They have a good amount of locations now, but one is located just steps from the Vatican Museums! This location is called Be. Re. + Trapizzino I guess because it sells beer too. But they have the authentic and delicious Trapizzini! And don’t worry, you’ll have the opportunity to have them again in Florence, so don’t be too sad that you can only fit one in your stomach at a time.
Tori Tip: They have a location in NYC!!! If you’re visiting the Big Apple any time soon, or live there, be sure to visit. We went recently and they were just as amazing as the ones we had in Rome and my family was blown away. They said it was the best food they had during their trip to New York!
Pickup your Rental Car
Rome has been amazing but it’s time to explore more of your 2 week Italy trip itinerary! Head to Roma Termini, the main train station, to pick up your rental car. Obviously book a car in advance!
Give yourself plenty of time because they can be a little slow, plus you have to walk a block or two to get to the parking garage where the car is, but it was very easy and everyone was so nice.
It’s also important to note that you will need an international driver’s permit in order to drive in Italy. It’s super easy to get and I have provided more information in the tips section at the end of this post!
Tori Tip: If you have more time in Rome (lucky you!!!) be sure to read my article on relaxing things to do in Rome for more ideas!
Drive to Tuscany
Once you get in the car head straight out of the city. Driving in Rome can be crazy, but being at the train station you are already in the outskirts of the city, so keep driving out, and drive slow, and you’ll be perfectly fine. Plus, they drive on the right side of the road here, so us Americans will feel right at home.
You’ll spend the afternoon driving through the countryside of Umbria and into southern Tuscany. It will take about 2 hours to get there. The second you spot the first rolling hill, you definitely might cry. I know I sure did. Cry away, you’ve made it to your “Under the Tuscan Sun” moment.
Check into Your Hotel in Saturnia
Get to Saturnia and stay at Villa Acquaviva for the night. It’s the absolute cutest little B&B in the rolling Tuscan Hillside. The rooms are so cute and perfectly clean and comfortable. The property is beautiful, and they have a dog that lives on property and is so, so sweet.
I cannot tell you how much we loved staying here and wished we could have relaxed for a week at this sweet hotel. They have a pool during the summertime, property to wander, views of the hills and an incredible restaurant on property to enjoy. Plus, free breakfast in the morning!
Siesta
Relax in your room and get ready for dinner. It’s been a long day!
Dinner at La Limonia
Walk across the property to the restaurant, La Limonia. This meal was also high in the rankings for my favorite food in my 2 week Italy trip itinerary. In fact, everything you have in Tuscany will be that way!
Sit down for a long, quiet meal with fabulous service. Get a bottle of wine that they made on property. Did I mention this hotel also has a vineyard!?!
The menu is seasonal, so sadly I cannot recommend a specific dish. But order as much as you can and share because it is all so, so good.
After dinner, wander back home and get a really great night’s sleep. The night we stayed here it rained and the tapping of the rain on the terracotta roof with a bellyful of pasta and wine was the most magical evening I could have imagined.
Day 4: Tuscany
Saturnia Hot Springs
Wake up early and put on your swimsuit because we’re heading to the Saturnia Hot Springs! They’re natural sulfur hot springs located in the middle of the rolling hills of Tuscany. A stunning sight to see. It’s just a quick drive from the hotel. Be sure to stop at the overlook just before you get there!
Once you pass the springs, drive another second and on the right will be a parking lot. Be sure to have a few euro coins to pay the meter.
The springs are gorgeous and warm but be prepared, it does stink a bit like sulfur. It wasn’t too bad when we were there though! I have an entire guide on visiting the Saturnia hot springs that you need to read before your visit for all of the best tips!
Breakfast at the Hotel
Head back to the hotel once you’re done relaxing in the springs. Shower and get ready for the day then head down to the lobby for a quick breakfast. Of course if you’d rather get breakfast before the springs you can definitely swap these two.
Drive to San Gimignano
Hop in the car, say goodbye to Villa Acquaviva and drive another 2 hours north to San Gimignano. This hillside town absolutely stole my heart and I know it will steal yours too. You’ll get to enjoy a day in San Gimignano.
Lunch & Wine Tasting at Tenuta Torciano
First stop is Tenuta Torciano Winery located just outside of town. It’s the cutest vineyard and tasting room with the kindest staff and incredible food and wine!
Be sure to book the Lunch & tasting in Winery in advance, which includes a large wine and olive oil tasting and a 3 course meal! The food is to die for. You’ll never want to leave!
Be sure to order some wine and olive oil to be shipped home, as well!
Tori Tip: If you decide to skip the drive through Tuscany on your 2 week Italy trip Itinerary, then instead you can book this tour for a visit to the vineyard from Florence!!
Check into Your Accommodation in San Gimignano
Once you are ready to leave, make the short drive into town and check into your accommodation. I highly recommend a VRBO like this one in San Gimignano so you can feel like a local for a day in this charming Tuscan village. It’s my absolute favorite of the towns near Florence.
There are so many cute ones to choose from, I’ll list a few I love below!
Option #1
Option #2
Option #3
Option #4 – Perfect for a larger group. Has 4 bedrooms, a pool and epic Tuscan views!
Gelato at Gelateria Dondoli
One of the main reasons….okay truthfully, it was THE reason, we came to San Gimignano out of all the gorgeous Tuscan towns was for the gelato! Gelateria Dondoli, located right in the heart of town, is a world champion gelateria. They are known for winning the title of “best gelato in the world” and I had to try it for myself.
And while the gelato sure was amazing, the town is even better, so I am so glad it brought me here, you will be too!
So head over to Dondoli and grab a few scoops. I love pistachio and bacio (chocolate hazelnut)!
Siesta
You might be ready for your siesta by now, so with a belly full of gelato take a quick nap. Many of the shops close now anyways, so you might as well!
Wander the Cobblestone Streets
Once you’ve rested a bit, get out and explore. San Gimignano is tiny so you’ll be able to walk the whole thing. Explore the cobblestone alleyways and enjoy the many walking paths around town.
If you’re looking for something else to do. Visit the Civic Museums and climb the Torre Grossa (big tower).
Dinner at Le Vecchie Mura
For dinner, get a reservation at Le Vecchie Mura. A table here offers stunning views out over the rolling hills, delicious food, endless wine and friendly staff. You cannot go wrong!
Be sure to order some Tuscan specialties including ribollita (Tuscan soup), tagliatelle cinghiale (tagliatelle pasta with a wild boar meat sauce) and Bistecca alla Fiorentina (“T-bone” Beefsteak -famous for its thickness-grilled). But in a few nights I will be recommending you order the Bistecca, so skip it for now if you don’t want it twice!
Day 5: Tuscany & Florence
Breakfast at a Local Bar
Get up early and prepare yourself for a long day exploring Tuscany with a delicious cappuccino and croissant from the local bar.
Drive to Pisa
Drive a little over an hour to the town of Pisa, home to a very famous tower.
See the Leaning Tower of Pisa
Once you get to town, find some parking nearby and walk to the leaning tower of Pisa. Get your photo doing the famous “hold up the tower” shot and any other silly photos you want to take. It might feel dumb but “When in Rome…I mean Pisa”!
You can also choose to climb the tower if you’d like. And you might as well because there’s not much else to do in town. To climb the tower you will need to buy a ticket and make a timed reservation in advance. These absolutely sell out so be sure to book before you leave for your 2 week Italy trip Itinerary. The ticket will cost €20 per person and gets you access to the cathedral as well.
The climb to the top is 251 steps and the entire visit will take about 30 minutes.
If you decide to go into the cathedral, make sure your shoulders and knees are covered. Bring a light shawl if you’re wearing a sleeveless shirt!
Drive to Lucca
After you’ve climbed the tower, hope back in the car and start heading towards Florence, with a stop in the adorable town of Lucca. It will take about 30 minutes to get there.
Have Lunch at Osteria al Borgo in Lucca
Once you get to Lucca, you’ll probably be ready for lunch. Head straight to Osteria al Borgo for a simple, authentic and delicious meal. The ravioli special must be tried here!
Explore Lucca
After lunch, I spent some time exploring. Lucca is known for the walls that encircle the city. They are no ordinary walls, they have gardens on top of them! You must spend time here enjoying the park along the walls.
Drive to Florence
Once you’re done exploring (or it’s getting too late) make your final, 1 hour and 15 minute drive into Florence. Drop off the rental car and head to your hotel.
If you have more time in Tuscany and are looking for other things to do, read my guide on a weekend in Tuscany!
Check into Your Hotel
With so many places to stay in Florence, it will be hard to choose. We stayed at the Westin Excelsior, Florence and it was an incredible hotel. It’s located right on the Arno River, and everything is within a short walk. Including some of the best restaurants and gelato shops!
The rooms are super large (for Europe) and beautiful. The whole building is beautiful and ornately decorated. You cannot go wrong staying here.
Another great option is the Sina Villa Medici. Located a tiny bit further from all of the main sights, but still super easily walkable.
Siesta
Once you’ve made it to the room, kick back and relax a bit until you’re ready to head to dinner.
Dinner at Mercato Centrale
For dinner tonight, walk to the Mercato Centrale in the heart of Florence. This is a market by day and a food hall by night (well, the food hall is open during the day too). It’s a great opportunity to try a little of everything, and let each person pick what they’re in the mood for. Plus, the food is pretty inexpensive, and everything is very local and authentic.
When you approach the building, it will probably look closed, at least it did to us. But don’t worry, walk around until you find the escalator and head upstairs. Then it will be a whole different world as it will likely be super packed! And you’ll see lots of locals here too.
Feel free to try out anything that looks delicious. But you’ll likely be tempted to have another Trappizini, I know I was! If for whatever reason you didn’t get one in Rome, you MUST have one tonight!
Gelato at Gelateria Perché No
If you have any space left, head over to Perche No for gelato. It’s creamy and delicious and one of our favorites from our 2 week Italy trip!
Day 6: Florence
Visit a Museum
This morning you’ll have time to explore a museum. Florence is known as the “Jewel of the Renaissance” and is the epicenter of art in Italy. Sure, there’s art all over the country, but this is where you’ll see the most by far! But be sure to go as soon as the museum opens, it will get incredibly busy in just a few hours!
You have to decide which museum you’d rather visit this morning. Here’s two most popular options:
Accademia Gallery: This art gallery is filled with paintings, sculptures and other mediums by famous artists including Michaelangelo, Botticelli, Giambologna and more. The Accademia is most well known for being home to Michaelangelo’s Statue of David. The cost to enter is €16 per person.
The Uffizi Gallery: The most visited museum in all of Italy (since the Vatican Museum is technically located in another country, Vatican City) is the Uffizi Gallery, filled to the brim with art mostly from the Italian Renaissance. You’ll see works by Leonardo da Vinci, Michelangelo, Raphael, Botticelli and more. Possibly the most famous piece here is the Birth of Venus. The cost to enter is €25 per person.
Whichever museum you decide, you should absolutely consider booking a guided tour. Otherwise, you’ll see a bunch of art and probably not learn very much about it or understand what you are seeing. Plus, if you are like us, it will be…not that interesting. But a tour guide makes it fun, engaging and super interesting!
This is a great tour for the Accademia, and this is a great tour for the Uffizi Gallery. Or, if you want to fit both museums into one morning then I highly recommend booking this combined 3 hour tour! It’s the only way to realistically see both this morning. If you decide not to book a tour, be sure to only buy tickets directly through the museums linked above!
Have a Panini for Lunch
One of the most famous meals that Florence is known for are their sandwiches, or panini. You’ll find them all over Florence, or all throughout your 2 week Italy trip, for that matter. But one place in Florence has risen above the rest; All’Antico Vinaio. They have grown so quickly that they have 3 storefronts all within 10 steps of each other, with a massive line wrapping around the corner.
See what the hype is all about, hop in line and wait your turn to get a massive panini filled with freshly shaved meats. All of the sandwich options are good, but we recommend asking what your sandwich maker loves and getting what they recommend. The locals always know how to do it.
Climb the Duomo
It’s time to work off your lunch, and you’ll definitely get a great workout climbing to the top of the Duomo. It’s easily one of the most iconic things to do during your 2 week Italy trip itinerary and cannot be missed.
You’ll have to climb 463 narrow steps up to the top of the dome, and then you’ll be rewarded with sweeping views of the city. It’s breathtaking and an absolute must while you’re here in Florence.
It’s an absolute must to buy tickets in advance because they sell out weeks beforehand. Tickets cost 30€ and also include access to the rest of the property. This includes the Bell Tower, Museum, Baptistery and Santa Reparata. Be sure to climb to the top of the Bell Tower as well to get views of the dome!
Since you’ll be going inside the church for this you must have your shoulders and knees covered! Bring this light shawl with you if you wear any tank tops!
Siesta
After the climb you’ll definitely be exhausted and ready for a siesta, so go back to the hotel, rest and get ready for dinner!
Aperitivo at Golden View
Located right on the Arno River, Golden View is a great spot for Aperitivo. Order a drink, some light snacks and enjoy the sunset as the city glows a bright orange before the sun goes down. The views here are fabulous!
Dinner at Parione
Cross back over the river and up two blocks to Parione, the best spot in Florence for dinner! Make a reservation in advance to guarantee you can get a seat. You’ll find locals and visitors alike eating here, which is always a great sign.
We enjoyed one of the best meals on our 2 week Italy trip itinerary at Parione. Tonight is when you must order the Bistecca alla Fiorentina; a huge t-bone steak that is a staple of the region. They serve it in a traditional style with potatoes and beans. And it is all incredible.
We also ordered an appetizer of buffalo mozzarella and a bottle of house red wine. It was the most perfect dinner; everything was exceptional.
Gelato at Gelateria La Carraia
If you’re anything like us, you’ll need to top off the perfect dinner in Florence with a cone of gelato. Walk back across the river for dessert at Gelateria La Carraia. The gelato here is wonderful.
Day 7: Florence
Cooking Class
So I know I’ve said this a lot, but truly one of my favorite parts of our 2 week Italy trip itinerary was our cooking class that we took in Florence. The food in Florence (and all of Tuscany) was the best we had in all of Italy, so there’s no better place to learn how to cook Italian food!
There are tons of cooking classes to choose from in Florence but we went with the Florencetown Diadema Cooking School and it was out of this world!
Start off with the group by visiting the local market, learning about the food you’ll find there and buying what you need to cook. You’ll spend a few hours in the kitchen with your teacher learning how to make pasta from scratch, the sauces to go with it, and a delicious tiramisu to top off the meal.
And then once it’s all done, you’ll have a huge meal eating all that you cooked with unlimited red wine. And you can make new friends with the other tourists in class; we did and it was the best.
Why take home things when you can take home new skills instead? I know I’d rather know how to cook authentic Italian food than have a keychain, that’s for sure!
It’s important to note that the market tour is not included if you book the class on a Sunday in Florence because the market is closed that day.
Siesta
After all that unlimited wine you probably should head back for a siesta.
Walking Tour of Florence
Get back out into Florence and see more of the city. Turn on Rick Steves’ tour of Florence and take in the sights.
Leather School
While you’re out, be sure to stop by the Scuola del Cuoio, the Leather School in Florence. The most famous item that Florence is known for producing is leather. Here you can watch the artisans craft belts, bags and more and learn about their work. You can also buy authentic leather items here and trust that they are indeed genuine Italian leather!
Sunset at Palazzo Michelangelo
Easily the most popular viewpoint in all of your 2 week Italy trip itinerary is the view of the sun setting over Florence from Piazzale Michaelangelo. Walk through the neighborhoods up the hill to get to this spot, find a spot to sit and relax as you watch the colors take over the sky. Alternatively, take a taxi up the hill and walk back down after.
We were unlucky enough to get a super gloomy evening, but chances are you’ll have much better weather and get this iconic experience. You can even bring a bottle of wine to enjoy as you wait.
But this viewpoint is no secret, so get here early if you want a prime spot.
Dinner at Gustapizza
As you head back down to town, you’ll pass through the Oltrarno neighborhood which is home to Gustapizza, your dinner spot for the evening. This is a super popular spot in town for pizza, and let me tell you why. It’s incredible!!! We still dream of these pizzas to this day, they are that amazing. You can either wait in line for a table, or skip the line and order to-go, and take it back to the hotel for a chill night in the room.
Gelato at La Strega Nocciola Gelateria
If you stayed out and ate at the restaurant, then you’ll want to stay on this side of the river for one last thing, gelato! La Strega Nocciola is known for having some of the best, creamiest, most authentic gelato in Italy. And its prestige is deserving. The gelato is fabulous.
Day 8: Venice
Hop on the Train to Venice
Sadly, the time has come to leave Florence, and now you will head to Venice! Get a taxi to the train station and hop on the train to Venice, one of the best cities in Northern Italy. As always, get your tickets in advance. You must read all of my train travel tips that I have included at the bottom of this article as it’s super important!
Buy Vaporetto Passes
Once you step out of the Santa Lucia train station you’ll immediately get views of the Grand Canal. Hop in line to get a 48 hour ticket (35 €) for the Vaporetto, Venice’s water bus. For some great information about buying vaporetto tickets read this article.
Take the Vaporetto to Your Hotel
Once you have the passes, jump on the next vaporetto heading towards the direction of your hotel. Check out this Vaporetto map in advance to make sure you get on the right boat.
Check into Your Hotel
Check into your hotel and get unpacked before exploring the floating city! Here’s our recommendations of the best places to stay in Venice.
Okay so truth is, we stayed at the Gritti Palace. An old stunning hotel located right on the grand canal with room rates starting at welllll over a thousand dollars a night. I know that probably sounds absurd to you, and it would to me too, but my sister who works at Marriott got us a ridiculously great deal.
So I don’t expect you to stay there, unless you can afford that, then go for it honey, cause the place is jaw-dropping fabulous,
Instead, consider staying at the AC Hotel Venezia which is pretty close to the train station, or the JW Marriott which is located on its own private island, how stinking cool!!
VRBO is also a really great option in Venice because you’re likely to get canal views from your bedroom for a much lower price than a hotel. I think this apartment with a rooftop terrace would be fabulous, or this place with grand canal views!
Wander Around Venice
One of the best parts about Venice is just wandering around and getting lost in the alleyways. Spend some time exploring and finding beautiful places in the floating city.
Have Lunch at 6342 A Le Tole
Wander your way over to 6342 A Le Tole for lunch. A quaint spot with a modern Italian menu. There’s plenty of delicious pizzas and pastas to choose from so there’s something for everyone.
We ate here during our 2 week Italy trip and it was possibly the best spot in all of Venice. Everything was fresh and made in house and so, so yummy.
Take the Audio Tour of Venice by Vaporetto
Make your way to the train station. This means a 9 minute walk to ferry terminal F.te Nove “C” plus a quick ride, or a 30 minute walk directly to the station.
From here, you’ll hop on line 1 and ride the vaporetto while listening to Rick Steves’ Grand Canal Cruise audio tour.
Get Cicchetti
One of the dishes that Venice is most well-known for is the cicchetti. Essentially a small plate, or little snack, the cicchetti can be found all over the city. The most common cicchetti you’ll see is a little slice of bread with a topping. The toppings range from tomatoes to anchovies, cheese to vegetables.
Check out this guide for the best places to find cicchetti in Venice and order a plate of little snacks!
Watch the Sunset from the Rooftop
The sun will be going down soon, so you’ll want to head to the rooftop of Fondaco dei Tedeschi near the Rialto Bridge. You can visit for free, but a reservation is required since it’s such a popular spot.
Have Dinner at Ristorante La Piazza
For dinner tonight, make reservations at Ristorante La Piazza. You’ll get to try authentic Venetian cuisine here with great service. They’re known for handing you a glass of prosecco upon arrival. What’s better than that?!
I recommend you try something with seafood; you are on the coast after all!
Gelato at Gelatoteca Suso
Another one of the absolute best gelatos we had during our 2 week Italy trip was at Gelatoteca Suso in Venice! Everything was right about this gelato. It was creamy and homemade and devine. Get a few scoops and head back to the hotel for the night!
Day 9: Venice
Breakfast at Rosa Salva
A super popular spot in Venice for coffee and baked goods is Rosa Salva. Head here bright and early to fuel up for the day.
Take the Vaporetto to Burano
Walk to the Fondamente Nove Ferry Terminal on the northern side of the island and jump on the 12 line to Burano. And please trust me, this is the best option! Even if there is a terminal closer to where you are, you do not want to get on anywhere else or the boat ride will take FOREVER!! Not like we know from personal experience or anything…..
Once you are heading away from Venice to the island of Burano, sit back and relax and enjoy the views of the water.
Wander around Burano
You’ve made it to the famous island of Burano, the most colorful island in Venice! Spend as long as you want exploring the bright and beautiful island, and take tons of photos.
I highly recommend you wear a white dress today to stand out among the colorful buildings in your pictures.
Have Lunch at Riva Rosa
Once you’ve worked up an appetite head over to Riva Rosa and get a table for lunch. We were lucky enough to get the most perfect table right on the canal for views of the water, island and people walking by. It was perfect.
And the food? Delicious!! I highly recommend you get exactly what we had, and what the island is known for. The Gran Fritto Misto is a plate of mixed fried seafood and vegetables. It’s unbelievable. And the other popular dish is the Risotto, which was also so, so yummy. We licked our plates clean.
Visit the Lace Museum
After lunch, visit the Lace Museum. Other than fried seafood (ha!), Burano is known for its lace making! Visit the museum to learn all about the history of the lace on the island and buy some to bring home!
A visit to the museum will cost between 22€ and 40€, depending on how many people are in your group.
Take the Vaporetto to Venice
Once you’re done exploring Burano, hop back on the vaporetto to Venice.
Visit St. Mark’s Square
The most famous spot in Venice is St. Mark’s Square and St. Mark’s Basilica. You can book a guided tour and/or climb the bell tower. Or just admire it from the outside if you’re museumed-out at this point.
Go on a Gondola Ride
It’s not cheap, but it’s probably pretty high on your bucket list for things to do during your 2 week Italy trip itinerary. Going on a gondola ride around Venice of course!
You’ll find gondoliers all over the city waiting to take you around for a ride, and now that the sun is likely about to start going down, it’s the perfect time to sit back, relax and enjoy the ride.
Have Dinner at Ai Promessi Sposi
Have dinner tonight at Ai Promessi Sposi, one of Rick Steves’ favorite places to eat on the island. And you can trust him, he is the Europe Guru!
The menu was a little intimidating to us as most of the items looked like things we had never really tried before, especially in Italy. We actually almost left. But I’m so glad we didn’t because everything truly was delicious and not as unusual as we had expected!
The service was fabulous, they even split the pasta dish for us since we were sharing a few different things, which was so unnecessary and kind! We also had scallops and salmon with potatoes and it was all delish.
Wander Venice at Night
It’s your last night in Venice, so explore the city as much as you want.
Day 10: Pompeii
Take the Train to Naples
I encourage you to get up early every morning, but today I recommend you get up REALLY early! Book the first train out of Venice heading towards Naples! As always, get your tickets in advance. You must read all of my train travel tips that I have included at the bottom of this article as it’s super important!
Get a Private Driver
After you arrive in Naples you’ll want to have a private driver there to pick you up. I cannot recommend Joe Banana Limos enough. They were absolutely fabulous to work with, and the prices were reasonable.
If they are booked up, do not worry as there are tons of other private driver companies to choose from!
Visit Pompeii
Book a private transfer to Positano with a stop in Pompeii. When they ask you if you want to book a tour through them of the city of Pompeii, don’t hesitate and say yes! We made this mistake and did not book a guide and it was such a shame. We didn’t understand a lot of the history and couldn’t appreciate all of the ruins we saw. Book the guide!
If you want to book a tour separately from your transportation, this is a really good tour of Pompeii!
Check into your Accommodation
Once you make it to Positano, check into your accommodation for the next few nights. Make sure to catch your breath after getting a glimpse of that view! I was so tired and honestly in need of a shower and nap at this point, but I was rejuvenated the second I saw Positano. It’s one of the best beach towns in all of Italy!
I highly recommend you book a vacation rental here because the hotel prices can be prettttyyy wild. We stayed in a vacation rental and absolutely loved it!
Here’s some VRBO and Airbnb options that look amazing!
Gema Suites – Abisso: This is where we stayed and it was absolutely perfect!!
Yellow Casa Dama
Positano Little House
Buy a Bus Ticket for the Morning
You have a great adventure planned tomorrow, and you’ll need to plan ahead. Ask your host where you can buy a bus ticket to get to Bomerano. From my understanding, the places that sell them change, so it’s best to ask a local. Otherwise, see if they offer rides. Many hosts will take you where you need to go for a reasonable fee!
Have Dinner at La Tagliata
Have dinner reservations made for the famous La Tagliata. It’s located high in the mountains above town but they provide free transportation. Make sure you tell them when you book that you’d like a ride, and call a few hours beforehand to confirm.
The views from the restaurant are obviously stunning, but the food is the reason you’re here. For a set price, they bring out round after round of food! The menu is basically whatever the chef feels like preparing tonight, but will always include appetizers, breads, pastas and desserts. There’s SO much food you will have no way to eat it all.
Day 11: Positano
Grab a Quick Breakfast
Head to the nearest bar, grab un cappuccino and a pastry, and head to the bus station. It’s time to hike the Path of the Gods!
Bus to Amalfi
Hop on the bus to Amalfi as early as possible. You can check the timetable here. Just note, the buses are not 100% timely or reliable so be flexible and prepared to wait. Or, you can certainly hire a taxi or private transfer if you’d rather spend the money and have less headache! The bus ride is about 45 minutes long.
My friends Adam and Kathryn from Adventures of A+K took the buses to hike the Path of the Gods and explain in detail how to do it. I recommend you watch their video before you go! They also include some good information about it in their blog post about their time in Positano.
Hang out in Amalfi
Spend an hour or so exploring Amalfi. Be sure to stop at a market to grab a lunch to take with you on your hike. Bread, prosciutto and cheese makes for a great lunch along the trail. And plenty of water of course!
Bus to Bomerano
When you’re ready to get hiking, catch the next bus to Agerola (Bomerano). You’ll get off here and be very close to the trail!
Hike the Path of the Gods
The Path of the Gods is a 5.8 mile point-to-point trail that has about 1,200 feet of elevation gain. It’s rated as moderate hike and is definitely doable for the average hiker.
The views all along the trail are jaw-dropping! Plus you’ll see locals, animals, lemon groves and more exciting things along the way. At the end of the hike is a little stand called Lemon Point where you can buy a cold and refreshing lemon treat. Then you’ll walk the 1,700 steps down to Positano to end the adventure.
Relax on the Beach
After a long day, relax on the beach and feel free to do nothing, you’ve earned it!
Dinner at Chez Black
Find the energy to get showered and dressed and head to Chez Black for dinner. Located right on the beach, this spot is definitely touristy given its prime location, but don’t let that scare you because the food is actually super delicious. Order the heart shaped pizza and an arugula salad!
Day 12: Capri
Take a Boat Tour to Capri
Today you’ll take a day trip to the Island of Capri! This island holds a special place in our hearts…it’s our baby girl’s middle name! And I’m sure you’ll love it as much as we did.
Capri is located off the coast of Sorrento and is the most charming beach town. It’s known for being a vacation spot for the rich and famous, but don’t worry it’s super accommodating for all budgets nowadays.
Be sure to book your day tour in advance. This is the tour we did and it was incredible! The perfect way to get a taste of the island. The guide was fabulous, the boat comfortable, and it was so fun to meet the other travelers. We even met a couple from Nashville, where we live!
Since this is day 12 of your 2 week Italy trip, you’re probably very tired at this point. My husband was asking me if we could skip this day but I told him there was no way to miss it. And he is SO glad I made him go because he said it was his favorite day of the whole trip!
As you approach the island your guide will take you on a loop around to show you some of the top sights including the Blue Grotto and the Faraglioni Rocks.
Be sure to bring a swimsuit and towel as you’ll likely have an opportunity to jump out and swim in the crystal clear waters. Even if you don’t want to swim, I highly recommend you pack a Teema Towel. They’re so light and compact, but will be the perfect thing to keep you warm on the boat when the wind is a bit chilly and the water is spraying up.
Take the Funicular to Town
Once you make it to the port, hop off the boat and explore for a few hours. The area near the post is the most touristy so I recommend you immediately head up the hill to the center of town. You can hop on the Funicular, which is a 4 minute cable car ride up the hill.
Alternatively, walk the path that starts here to the top. It’s a hike but honestly not too bad and only takes about 15 minutes. This is what we did since the Funicular was packed when we arrived.
Shop in Town
Spend some time shopping and wandering the alleyways! We loved the high end boutiques here, my husband had a great time trying on fancy linen shirts and high end sunglasses.
Get Custom Leather Sandals Made
But the most famous shopping experience in Capri (and possibly all of this 2 week Italy trip itinerary) is getting custom leather shoes made to fit your feet.
There’s tons of shops that make these sandals for you, but I found A Mano Capri which had a beautiful storefront, friendly employees and reasonable prices. It was the perfect place to have my sandals made, they were ready quickly and they turned out perfect! This is a must-do while on the island.
Have Lunch at Da Paolino
By far the most beautiful restaurant we ate at during our 2 week Italy trip was Da Paolino on the island of Capri. The tables are nestled under a lemon grove and create the most romantic and unique setting for lunch. PLUS, the food is devine!
You’ll need to make reservations here very far in advance, so submit a request on their website as early as possible to guarantee a seat. They fill up FAST and it’s easy to see why!
I had the lemon ravioli, because obviously I had to have a lemon dish, and it was wonderful. And oddly enough, we LOVED the arugula salad here. It was so simple but everything was incredibly fresh, we could not get enough of it.
Enjoy a Lemon Granita
After lunch, walk back down to the port. Before you get back on the boat, buy a lemon granita from one of the stands as a refreshing dessert! It’s a popular item you’ll find on the island and all along the coast.
Take the Boat Back to Positano
Once it’s time to meet, head back to the boat for the ride back to Positano. You’ll likely get to jump out and swim if the weather is nice enough!
Dinner at Casa Mele
For dinner tonight you’ll be heading to an upscale spot called Casa Mele. This place was recommended to us by our private driver from Joe Banana Limos and he was spot on; everything was amazing!
It’s definitely one of the most upscale restaurants on the 2 week Italy trip itinerary, but it’s worth spending a few extra bucks for since everything is so delicious. But be sure to ask for extra focaccia, since it’s free and SO darn good!
The menu changes often based on the fresh ingredients available. But one of the dishes we had was similar to a cioppino, a seafood stew, and it was phenomenal!
Visit Music on the Rocks
If you still have any energy, head down to the beach and visit Music on the Rocks. It’s a club located inside of a cave, how cool!
Day 13: Positano
Spend the Day at the Beach
You’ve made it! The day where you get to relax on the beach and recharge from a very busy 2 week Italy trip itinerary.
If your budget allows, I highly recommend you book a spot at Arienzo Beach Club Positano. It’s not cheap, but the high price includes reserved beach chairs and umbrellas, a bottle of prosecco and lunch!
If the beach club is not your thing, instead walk over to Fornillo beach. A smaller beach that is much less crowded than the main one in Positano!
Grab lunch at a spot on the beach and enjoy the views.
Go Shopping in Positano
Make sure to spend some time shopping and buy anything you’ve had your eye on. For my husband that was a pair of Italian leather shoes from the shoe store, and for me, the hand painted plate from the pottery store.
Visit Franco’s Bar
Another famous spot in Positano is Franco’s Bar. Head here for aperitivo for a drink and to watch the sunset. You will need reservations though, so plan in advance!
Have Dinner at Il Tridente
For your final dinner in Positano, head to a place with great food and epic views, Il Tridente! The service here is incredible and the food is top notch.
Day 14: Rome
Grab Lunch from the Market
Before you leave Positano, grab a quick picnic lunch from the market, you’ll thank me later!
Private Transfer to Naples
Schedule Joe Banana Limos to arrive and pick you up to get to the Naples Train Station. Don’t be like me and forget to schedule the return trip….clearly I didn’t want to leave!!
But Joe Banana Limos took care of us and we didn’t even miss our train!
Train to Rome
Hop on the train back to Rome and eat your picnic lunch on the way!
Check into Hotel
Check into your hotel for one final night in Rome. I listed out my favorite hotels in Rome under day one, but if you’d rather stay by the airport, here’s a few hotel options instead.
Hilton Rome Airport
Hilton Garden Inn Rome Airport
Dinner at Ginger
If you stay in Rome the final night, grab dinner at Ginger. This might sound crazy, but by this point in our 2 week Italy trip we were ready for some American food. We could not have been happier with a burger and acai bowl. Yum! Ginger was the perfect option after all of that pizza and pasta!
If you want one last Italian meal, head to Mimi e Coco near Piazza Navona for a delicious traditional Roman dinner.
Then head back to the hotel and rest up for your busy travel day home.
When should you visit Italy?
One of the most popular questions people ask is when is the best time to visit Italy? And my answer will forever be: whenever you have the most time to go. Are some seasons “better” than others? Absolutely. But if you only have 1 week versus 2 weeks based on work or school schedules, I will always encourage you to go whenever it makes the most sense for you and your group.
However, if you are flexible with when you can travel for your 2 week Italy trip itinerary, then the absolute best times to visit Italy will be in the shoulder seasons. These are April & May and September & October. This is when the weather is the most beautiful, usually in the 70s, and when there are less tourists. Well, less tourists than the summer at least!
Summers in Italy are hot and crowded. There are SO many people visiting throughout the whole summer that everything is packed, sold out and expensive. That being said, if you only have the time off during the summer, then that’s OKAY! You should absolutely still visit, just make sure to set your expectations appropriately and be prepared. Book every single thing in advance, and start your days as early as possible to avoid crowds and heat. It will be an incredible vacation!
How to Get to Italy
Getting to Italy is easy since there are several major cities to fly in and out of. Rome and Milan will definitely have the most options from the US, but Venice, Naples and other cities throughout the country offer flights to and from the States as well. Find the one that makes the most sense for your timing and budget for your 2 week Italy trip itinerary!
If you are doing a tour of Europe, then you’ll likely want to arrive via train instead! Getting around Europe via train is so incredibly easy and usually pretty inexpensive. But sometimes flying within Europe makes more sense as flights can be super cheap and fast!
Tori Tip: For those wanting to explore two areas in Europe and fly between them you may want to look into the United Excursionist Perk! Basically, if you fly from the US to Europe, then a flight within Europe and then back home, the flight in between is free (just pay the taxes and fees!) Now the only catch here is that you have to be using United points to book this trip. But if you save up enough credit card points, this could be an awesome deal! You can read more about the United Excursionist Perk here!
How to Get Around Italy
Getting around Italy tends to be one of the most daunting tasks for first time visitors, but I promise you, it is SO easy! There are a few main ways to get around; train, rental car and private driver.
Train
You will want to get around Italy by train most often. Trains run between every major town and city and it makes getting around Italy super easy, convenient and fairly inexpensive!
There’s many different places online that you can look at and buy train tickets. However I highly recommend you use Trenitalia. They are the best, most trustworthy, easy to use and inexpensive option for buying train tickets. Download the Trenitalia app and do everything from there.
The major plus of using the app is that you don’t have to get your tickets validated if you are on any of the fast trains between large cities. All of the train rides recommended in this 2 week Italy trip itinerary uses those trains. If you book any of the slow regional trains, you validate your ticket by selecting “check-in” on the app.
If you buy any physical train tickets, you MUST get them validated or you could get in big trouble and slapped with a fine. This means you go up to the machine in the train station that’s located right before the tracks and you stamp your ticket.
I highly recommend that you book your train tickets in advance. Lots of people argue that they don’t want to buy them in advance because their plans might change, however if you want to follow my 2 week Italy itinerary at all, then you know you’ll have to plan every detail out in advance
Rental Car
Renting a car can be a great option any time you want to visit smaller towns. When you’re in the big cities, or going directly from city to city, a train is the best choice. However, if you want to explore areas like Tuscany, Umbria, Sicily and other areas like that, then a car could be a good option.
I will tell you, booking a rental car that has an automatic transmission was pretty expensive. It was something like 4 times the cost as a manual. If you know how to drive a stick, then you’re in luck!
In Italy they drive on the right hand side of the road and basically everything looks the same as in the States. Obviously all of the street signs are in Italian, but you can read the speed sign and I would argue that’s probably the most important.
If you do plan to drive in Italy, make sure you get an international driving permit. Head to your local AAA office to do so, and pay $20. It’s very easy, and legally required if you drive in Italy!
Private Driver
The place that makes the most sense for a private driver is on the Amalfi Coast. There’s no train to get you there and there’s basically no space for parking. So hiring a driver in advance is the perfect (and pretty much only) option! I highly recommend using Joe Banana Limos as they were incredible to work with!
There could definitely be other times where you would want to hire a private driver, like to or from an airport, or to and from a smaller town that doesn’t have a train station. In this case, use Get Your Guide or Viator to find a trustworthy company to pick you up!
Taxi
And last but not least, the taxi cab! Honestly, we loved using taxis while in Italy. We only used them in Rome and Florence, and they were awesome! There are taxi stands located all around both cities where the taxis line up and are waiting for customers. This makes it super convenient!
If you are not sure where the closest taxi stand is, then you can also call a taxi if you’d rather. Download the FREENOW App on your smartphone. The app works just like Uber or Lyft, you set your location, where you want to go and it will tell you the exact cost and how long to get there. It was SO easy!
The drivers almost always spoke great English and they were always so kind and respectful. We used them quite a bit, especially when we were hauling around our luggage!
Tips for planning 2 week Italy itinerary
Restaurants
Feel free to find other restaurants that fit your taste if you don’t want to visit any of the ones I recommend. However, whatever you do, do NOT visit any restaurants super close to tourist sites, ones with photos on the menu or ones that have people outside begging you to come in and eat. These are all signs that the food is awful!
Also, please please make reservations in advance for every single dinner. You do not have to keep all of them though! I understand that cravings can change, you might be too tired to go out, you might not feel like you could possibly eat even one more piece of pasta (yep it happens) or something that will change where you want to eat. And that is okay! Just cancel your reservation day-of and do something different. But at least this way you have something reserved and available for you should you want it.
My other reason that I recommend everyone has a reservation each night is that then the decision is made for you. I don’t know about you, but if we don’t have reservations one night after a long tiring vacation, my husband and I will 100% sit there and say “I don’t know, what do you want to eat?” back and forth and end up eating crappy hotel food. So avoid the stress and decision making and let “past you” make the decisions!
Gelato
Believe it or not, Italy is filled with bad gelato. It’s true! Tourist shops will cut corners and have stopped making the authentic, delicious, creamy gelato that you should be eating. You can trust that the places I recommend serve amazing gelato, but you can also find good gelato on your own with these tips.
I can speak from experience. I followed these tips during our entire trip and had only amazing gelato. Until one late night in Venice and everything seemed to be closed except this one spot on the main square. It screamed bad gelato, but it was our only option. And I actually threw the second half of my cone away. It was THAT bad!!!
Location doesn’t usually matter here. Good and bad gelato can be near top sights. What’s important is to look inside the shop at the gelato itself.
First, if the gelato is super bright and fake looking colors, it’s bad gelato! The pistachio should be a muted brownish green, not neon green! The exception here is the fruit sorbets, those can sometimes be super bright from the fruits themselves!
Secondly, the easiest thing to spot, and most important, you’ll see lots of gelato shops with the gelato piled high in big mounds. This always means the gelato is bad. Look for shops that have very flat, creamier looking gelato. Even better is if the gelato is covered with metal lids, that’s the best sign! It means they are controlling the temperature perfectly for the best gelato texture.
And finally, do your research. There is soooo much good gelato, so look up blogs writing about the best gelatos in each city you visit. Don’t trust Tripadvisor on this because the tourists (who usually don’t know any better) are the ones writing the reviews!
2 Weeks in Italy Packing List
For a full article about packing for Italy read my Italy packing guide!
But here’s some of the top things I recommend you pack for your 2 week Italy trip and why!
Portable Battery Pack – You’ll be out all day long using your phone for everything from sunrise to long after sunset. You’ll need it fully charged to take photos, call taxis, check your 2 week Italy trip itinerary and more! Bring this in your purse to recharge throughout the day!
Outlet Converter – In Italy the outlets are a different shape than in the US. Now you could bring an outlet adapter to change the shape, but that doesn’t affect the voltage. Italy’s voltage is different from ours and can fry certain items like a hair dryer/straightener/curler, and things like laptop chargers and more. Get the converter to make sure all of your electronics can safely be plugged in.
Reusable Water Bottle – You’ll need to stay hydrated throughout your very active 2 week Italy trip and will be drinking water constantly. Buying water bottles is expensive and bad for the environment, so I highly recommend you bring along a water bottle to fill up along the way. I used a collapsible one so that you can stow it in your bag easily when it’s empty!
Tori Tip: Rome is filled with water fountains to drink from or refill your bottle. The water is ice cold and completely safe to drink!
Teema Towel – I bring this towel with me everywhere! It is obviously great for using on the beach in Positano, on the boat to Capri and drying off at the hot springs in Saturnia. But it’s also perfect for a picnic in the Boboli Gardens, or keeping warm on the train to Venice. I use this thing constantly while traveling. It is the first thing in my suitcase!
Samsonite Suitcase – On that note, a high quality suitcase in Italy is an absolute necessity (we learned this one the hard way!!). The cobblestone streets (and sidewalks) are so hard on suitcase wheels and ours broke on like the third day! And while I’d love to be a backpack only kinda gal, that just ain’t me!
Shawl – Any time you enter a church in Italy you must have your shoulders and knees covered. Covering your knees is usually easy, a long dress or pants is cute and comfy. But the shoulders can be more difficult especially in the summertime. So I highly recommend you bring a lightweight shawl in your purse to throw over your shoulders whenever you happen upon a church you want to pop in. This will be especially important for the Vatican and the Duomo in Florence!
Euros – I highly recommend you get Euros from your bank before you leave! While most places take cards there are still many that require cash if you spend less than a certain amount. This happened a lot for coffee, snacks, waters, etc. How much you need will totally depend on each person, but I think we took about 500 euros and it was about the right amount!
If you use this 2 week Italy trip itinerary for your vacation I would absolutely love to hear how it went! Please email me with any tips, thoughts or questions that you may have at tori@toripinestravels.com. Have the best time! Ciao!