The Best Two Week Italy Itinerary

positano, italy

Beginning to plan for a once-in-a-lifetime trip to a dream destination can be very overwhelming. Additionally, you may never have the opportunity to go there again and if you’re like me, you have a limited amount of vacation time. I’d dreamt of a trip to Italy for years before finally committing and planning it. I put a lot of time and research into every aspect of the trip, and my two week Italy itinerary went smoothly and blissfully.

After traveling to numerous countries all over the world, I can confidently say Italy was my all around favorite place. The diverse landscape and atmosphere of different areas, the food, the history, the culture, the language, the wine, the romance, and the ridiculous beauty, all just blew my mind. So I’m here to help you plan the best Two Week Italy Itinerary so you can enjoy your dream trip as much as I did.

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General Tips for a Hassle-Free Short Two Week Italy Itinerary:

  • If the price is right, fly into one airport and out another to save time traveling in the country.
  • Make yourself a translation list of common words, phrases, Italian cities, and train station terms.
  • Pack light and do laundry if you need to. Rent an apartment with a washer and dryer. Hand wash socks and underwear occasionally if you don’t have access to a washer.
  • Download Google offline maps on your phone with Wifi before you go so you can use it data-free to get yourself around.
  • Read about train station procedures before you go. You can read my train advice HERE.
  • Scope out top reviewed restaurants with HERE or Yelp within walking distance of your hotel or apartment ahead of time, so you don’t waste time researching where to eat (like I always do).
  • If you decide where to eat on a whim, go where the locals are, not where the tourists are. Restaurants right in the piazzas or by major tourist sites will be more expensive and less authentic. As one person told us, “If the restaurant has pictures of their food, don’t eat there.”
  • Research and book day tours before your trip so you don’t waste time planning while you’re traveling. But don’t plan too many! Leave some room for improvisation.
  • Book your hotels/apartments ahead of time. Read reviews, look at pictures, examine map locations and Google Street Views.

Rome alleyways, Italy

Where have you always dreamt of visiting in Italy?

Make your itinerary about what is most important to you. If driving the countryside in Tuscany isn’t your thing (say what?!), or you’re all beached out and pictures of Capri just don’t do it for you, that’s fine, skip them. Here is my recommended two week Italy itinerary based on what I knew I had to see:

Two Week Italy Itinerary

Day 1: Rome

Arrive in Rome, get settled into an apartment (consider Airbnb where you can get travel credit by booking through my link) in a central location on a picture-perfect quaint street. Rest or grab a bite to eat. Walk to see the nearby sites: the Pantheon, the Spanish Steps, do some people watching in Piazza Navona, see Trevi Fountain. At some point, enjoy a fantastic pizza at Baffetto’s followed by a gelato at Frigidarium next door. The touristy areas of Rome feel incredibly safe at night, so wander the magical streets into the late hours. The view of Trevi Fountain is far better after dark.

Trevi fountain at night, Rome, Italycobblestone streets, Rome, Italy

Day 2: Rome

Make a mad dash for the Colosseum, taking in the Roman Forum along the way. Depending on where you’re staying, it could be a bit of a walk. But getting there early to beat the heat and the crowds is worth it. Depending on how much guiding you want, you could wait in line to tour the colosseum yourself, or join a group for a guided tour and skip the lines. A very popular option is a tour through Get Your Guide, which you can find HERE.

Later, head to the Vatican for a tour of the museums and St. Peter’s Basilica. Book ahead like I did HERE. Take into consideration that mass is usually held on Wednesday morning in St. Peter’s Square or the Basilica. The Vatican is on the other side of the river, so if your feet are killing you, grab a cab to get there. Vatican tours vary in duration and price, so consider your time constraints and research how in depth you want to go. If you can handle it, go back to the colosseum for a view at night.

colosseum, Rome, ItalyVatican, Rome, Italy

Day 3: Positano

Take an early fast train to Naples through Italia Rail, then transfer to the Circumvesuviana train (buy tickets at the train station in Naples) to Sorrento, then the Sita bus to Positano. It sounds complicated, and perhaps it was the most ambiguous day of travel, and took a few hours, but it really was worth it to get to the Amalfi coast affordably. If you can afford it, by all means, hire a transfer from Naples to save yourself the trouble. If you take the Sita bus, know which bus stop is closest to where you are staying and ask the bus driver to announce the stop, or sit near the front so you can be sure when to get off.

Relax and get acquainted with the heavenly Positano scene. Grab dinner with a view, walk the beach and the trail to the next beach. We rented a hillside home on AirBnB and couldn’t have been more pleased (or sore after hiking up and down).

views of Positano, Italycafe, Positano, Italy

Day 4: Positano

Rent a scooter and cruise the Amalfi Coast highway. Consider cruising up to Nocelle and hiking The Path of The Gods which gives stunning views of the coastline below. Some of my best memories of Italy are from our day of scooter cruising down the winding coastline during the golden hour of sunset.

amalfi coast views, path of the gods, positano, Italyriding scooter amalfi coast, positano, italypositano sunset views, italy

Day 5: Positano/Capri

Consider a day tour to Capri. If you have more time, stay overnight to enjoy the island without tourists. I sure wish I could’ve done that. We booked our boat trip ahead, but you could possibly go down to the beach in Positano the day before or in the early morning and inquire about availability that day. If you are susceptible to motion sickness, PLEASE take something for it before your boat leaves. I forgot, and it really put a damper on my day.

While in Capri, take the chairlift up to Mount Solaro. Capri is upscale, bustling, and deserving of more than a few hours, but if you’re short on time, I think a day is better than nothing. We loved our day trip with Cassiopeia. Also, if you want to use one of the adorable pink taxis on the island, ask some other visitors if they want to share the price.

views from mount solaro, capri, italycassiopea boat tour, capri, italypink taxi, capri, italy

Day 6: Florence

As painful as it is knowing you could spend the rest of your life in Positano, catch the bus, then trains back and arrive at your next destination: Florence. Settle into your hotel, I recommend Soggiorno Battistero – which is more of a B&B but right in the heart of the piazza facing the Duomo. It’s well priced, includes breakfast, and of course the location can’t be beat. Spend the afternoon and evening wandering the streets of Florence.

Duomo, piazza, florence, italypiazza, duomo, florence, italystreets of florence, italy

Day 7: Florence/Sienna/San Gimignano

Here’s where you’ll have to use your discretion. We chose to take a 12 Hour Tuscan Wine Tour so we missed a lot of what everyone raves about in Florence. I love art and museums, but personally wanted to visit some other towns like Sienna and San Gimignano, and Tuscan wineries more. One more day added to the itinerary would have been nice so we could’ve spent more time seeing Florence. But we stayed up late and made the most of our waking hours. This day could be easily spent visiting the major sites of Florence, and probably should be.

best gelato, san gimignano, tuscany, italy san gimignano, tuscany, italy

Day 8: Florence/Tuscany

Depending on what you were able to accomplish the day before, get up early and get somewhere before everyone else gets there. Since we barely scratched the surface of Florence, we spent our morning climbing Giotto’s bell tower right outside the hotel. You could choose to climb the Duomo instead, but the line was really long and we found the view from the bell tower of the Duomo to be fantastic. The climb up the narrow winding staircase was a bit claustrophobic, a bit dizzying and tiring, but the view was stunning.

florence duomo view from bell tower, florence, italy

After checking out of your hotel, take a cab to a car rental agency by the airport. It is much easier to drive out of Florence from the airport than the city center. Now here’s another tip: don’t bother with paying to rent the GPS units from the car rental company. Just download Google offline maps on your phone ahead of time, especially if you’re going to rural areas of Tuscany. Our rental car’s GPS touchscreen barely worked and it didn’t recognize the address we were going to.

Head out on your driving adventure to Tuscany. Which area to go, where to stay, driving in Italy, toll roads, etc. are all topics of their own, so I won’t get into that. We stayed at Hotelito Lupaia, which I can’t recommend enough. It is a truly magical farmhouse/villa from the 1600’s in a postcard-like setting near Montepulciano. After surviving your drive to your villa, check in and get to know the owners and explore your farmhouse property.

tuscan villa farmhouse, tuscany, italy hotel lupaia pool, tuscany, italyhotel lupaia, tuscan, farmhouse, tuscany, italy hotel lupaia, tuscany, italy

Depending on if your villa offers dinner, or how close town it is, enjoy a romantic dinner or go for a drive. We explored the tiny town of Montefollonico where we were the only tourists and no one spoke English. It was fantastic. We bought the biggest, juiciest strawberries and strolled the streets then came back to the farmhouse for dinner.

Montefollonico, tuscany, italy

Day 9: Tuscany

My favorite day of the entire trip. This is your day of Tuscan magic. Drive all over, stop at wineries (some require appointments), take pictures of the scenery, frolic through fields of poppies, explore medieval hill towns…this could all go on for weeks, but alas there’s never enough time.

This day was so jam packed for us. We got up before sunrise and took pictures as the sun came up over the rolling fields, then came back for breakfast and a cappuccino at the farmhouse.

hotel lupaia breakfast, tuscany, italytuscany sunrise, italytuscany rolling hills, italy

Next we explored Montepulciano then went to a sustainability winery and wine tasted and had lunch. We then went on a little road trip to find some hot springs, which were pretty amazing (although crowded) called Fosso Bianco in Bagni San Filippo. The drive was beautiful with almost no cars anywhere and pulling off to take pictures and admire the nonstop perfect sights was easy. We enjoyed dinner in Montepulciano that evening before retiring.

winery, tuscany, italymontepulciano, tuscany, italy Fosso Bianco in Bagni San Filippo, hot springs, tuscany, italyrolling tuscan hills, italypoppies in tuscany, italy

Day 10: Tuscany/Cinque Terre

One more day in Tuscany…just kidding, sorry. This is the whirlwind itinerary, not the laid back itinerary. Drive back to Florence, drop the car off, catch the train to the Cinque Terre. You wouldn’t want to miss these fabulous 5 villages on the ocean on your two week Italy itinerary. We rented an apartment (again through Airbnb) in Vernazza, but Manarola is stunningly beautiful as well and I’d a consider it a second choice. Riomaggiore is pretty neat too. Monterroso has a lot to explore (climb the hill and explore the incredible cemetery) and beautiful beaches, but it lacks the quaint charm that the other villages have, in my opinion. Explore your village, get dinner, watch sunset.

Vernazza waterfront, cinque terre, italy

Day 11: Cinque Terre

Buy your day pass for the trains and hiking trails at the train station. Start at one end and work your way down. Depending on your fitness level, time, and interests, you could hike between all the villages, a couple of them, or none. You can also take a ferry between the villages. We took the train to Riomaggiore, then to Manarola where we walked the first section of trail towards Vernazza to take pictures looking back at Manarola, then hopped back on the train to Corniglia, less picturesque from a distance, but with quaint alleyways. From here we hiked to Vernazza, which is one of the more difficult sections of trail, with plenty of uphill and uneven ground. In the heat of the day, we were sweating. The most difficult section is from Vernazza to Monterosso, but with our time being short, we chose to hop back on the train to explore Monterosso. Check ahead for certain sections of trail being closed to hiking. Consider bringing your swimsuit for some beach time in Monterosso. Make dinner reservations at one of the fabulous cliff restaurants in Vernazza for dinner during sunset.

riomaggiore, cinque terre, italy manarola, cinque terre, italy vernazza, cinque terre, italyviews of vernazza, cinque terre, italymonterosso, italy beach monterosso, cinque terre, italy

Day 12: Venice

Take the train to Venice. From the train station, you can take a water taxi (if you want to splurge) or buy a ticket for the Vaporetto (a water version of a city bus with set stops). Read this guide for more details. Download a route map with the timetable. You can either purchase a single ride or a day to week pass. Tickets must be validated before boarding.

Hopefully you’ve booked an apartment or hotel ahead of time and know which stop to get off at. I highly recommend an apartment with a roof deck. The views of Venice canals from above are priceless. Check in, get settled, then set out to explore the city.

rooftop Venice apartment two week Italy itinerary

I suggest booking a walking tour for the afternoon or next morning like THIS ONE. I felt it was greatly informative and educational if you want to learn about the history of Venice. If you’re crazy enough (or wealthy enough) to spend the money for a private gondola ride or shared gondola ride, great. Otherwise pay like €2 to take a traghetti, which looks like a gondola and it shuttles you across the Grand Canal in 8 different locations in about 5 minutes. To take a 40 minute gondola ride, you’re looking at about €80-100. Wander the canals and get dinner with a canal view.

venice canals, italyvenice grand canal, italyVenice canals, italy

Day 13: Venice

Explore Venice at your leisure. I definitely recommend getting up early. It’s incredibly special being able to get lost in the alleyways without the crowds. Of course see Piazza San Marco, Basilica di San Marco, Doge’s Palace, and any other historic sites that intrigue you. I think an organized tour like THIS ONE could help you appreciate it all more, and I wish we had opted for that.

Consider a boat trip to the island of Burano to marvel at the bright colors. I’m still bummed I didn’t do this. The colorful houses are so unique and whimsical.

But most of all, as you’ve probably heard many times, just get lost in the streets of Venice. Wear your walking shoes and eat and shop your way to the most picturesque bridges and canals you can. When your feet get tired, find a church. Sit and marvel at the architecture and delight in the cool shade for a bit. Hopefully you can catch sunset from the top of a roof somewhere. It truly is amazing.

canals of venice, italyvenice canals, italy

Day 14: Venice/Home

Grab a last cappuccino and say goodbye to Venice and Italy. Fly home from the Venice airport. We took a train to Milan and spent one night in Milan, because the flight was cheaper. The Duomo di Milano was truly spectacular to see, however, if I had the choice, I would not go to Milan if I was short on time. I’d rather have had another day elsewhere. But the duomo was quite stunning.

duomo, Milan, italy

Hopefully this whirlwind two week Italy itinerary has given you some ideas of how to structure your trip to see the most of Italy as possible and hit some of the better known highlights. There are endless, less popular, but certainly as incredible destinations that I can’t wait to visit someday.

If I could recommend one thing for all trips where you’ll be walking heavily, it is Pikolinos shoes. I discovered them in Positano, and have since bought two pairs of sandals. They are amazing and I tell everyone about them. And now, just from adding that link on this page, I literally just discovered they carry them on Amazon now!

Read this Ultimate Packing List for Italy

2 week 14 day italy itinerary

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11 thoughts on “The Best Two Week Italy Itinerary

  1. Sarah

    What a whirlwind indeed! Incredible itinerary. Makes me want to go back to Italy and do some of these places all over again.

  2. Michelle Joy

    Looks like a great itinerary. We’ve only spent a week in Italy but we managed to crunch a good deal in. Lake Como was my fav! We definitely need to go back though because there’s just so much to see.

  3. Carrie

    Wow, you really packed it all in in two weeks! I spent five weeks in Italy and still didn’t make it to the Amalfi coast or more rural parts of Tuscany. That farm house in the Tuscan countryside sounds really amazing.

  4. Varsha Gawai

    Nice itinerary. You guys had a blast. I also like Italy. There is much diversity in nature and culture that one needs to go there again and again; each time in the different season. My favorite places are Florence and Matera.
    You have captured your moments so nicely. Tuscany looks so amazing through your photos.

    1. Jessica Carpenter

      I couldn’t agree more about the diversity in Italy! From north to south, the landscape and “feel” just changes soooo much! And I love it all! Thank you for your kind comments!

  5. Elaine Masters

    Energizer bunny!! I’d love to be your sherpa. Oh to wander in your footsteps. I’ve visited Italy twice but too briefly and need to book two weeks or more to meander through villages, get up early and savor the light. Italy is too precious to rush and I need to return.

    1. Jessica Carpenter

      Haha, my sherpa! I love it. Italy is so precious! It’s is my most favorite place in the world. I’d love to go again so much. Even though we saw a lot in 2 weeks, it is definitely not enough.

  6. crystal

    That sounds like a lot to be done in 2 weeks but u did it! My family and I are planning to go in May to Italy, we do want to stay in Florence as well as Rome but we think we should squeeze one more city in there. What would you recommend. This will be our first time traveling and we have a 3 year old, so I don’t know if we would be able to accomplish everything you guys did.


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