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We’ve compiled the perfect itinerary for an unforgettable 2 weeks in Italy! While it’s a country you could easily spend months in, you can see a lot during your 14 days in Italy. This route will take you through many of the best places to go in Italy and certainly give you a taste of the amazing diversity of the country.
Places to go during your 2 weeks in Italy
- Rome
- Florence
- Pisa
- Cinque Terre OR Venice
- Tuscany (Chianti region, Siena, Asciano & Saturnia Hot Springs)
- Amalfi Coast
Overview of this 2 weeks in Italy itinerary
| Day(s) | City(s) |
| 1 | Fly into Rome |
| 2-3 | Rome |
| 4-5 | Florence |
| 6 | Pisa |
| 7-8 | Cinque Terre OR Venice |
| 9-10 | Tuscany (Chianti region, Siena, Asciano & Saturnia Hot Springs) |
| 11-13 | Amalfi Coast |
| 14 | Fly home from Rome |
Detailed Italy 2 week itinerary
This detailed 2-week itinerary takes you day by day through Italy. Since this itinerary is designed for you to experience as much as you can during 2 weeks in Italy, it includes the minimum days we would recommend in each place. Certainly consider spending more time in each location if you can swing it!
Day 1: Fly into Rome
Rome, the capitol of Italy, is a natural place to begin your trip. It’s also home to the largest international airport in Italy, Rome–Fiumicino, making it the most accessible city to fly into.
Since Rome in a large metropolitan city, spend your first evening orienting yourself with the city and eating your first of many amazing meals. Above all, don’t forget to indulge in gelato on day 1 as it should be a daily ritual while you’re in Italy!
While you’re planning, book 3 nights in your hotel in Rome.
Day 2-3: Rome
During your two full days in Rome, spend your time basking in the rich history and exploring the many world-renowned landmarks. While you’re here make sure to visit the Colosseum, Saint Peter’s Basilica and some of the most impressive museums in the world. Also save a bit of time for making a wish in the famous Trevi Fountain.
Day 4-5: Florence
Start day 4 by taking an hour and a half train from Rome to Florence, the capitol of Tuscany. In addition to being a great way to travel through Italy, it’s very simple to book your trains.
Florence is famous for its Renaissance architecture and art and is home to Michelangelo’s “David” sculpture. While you’re here don’t miss climbing the famous Duomo, visiting the Florence Cathedral and enjoying a sunset at Piazzale Michelangelo.
Note: Book 3 nights in your Florence hotel since your day trip to Pisa is round-trip from Florence.
>> Read all about the 15 BEST things to do in Florence!
Day 6: Florence to Pisa day trip
While Pisa is absolutely worth visiting, you can visit it during a day trip from Florence. So, in the morning on day 6 leave your belongings in your Florence hotel and grab a 1-hour train to Pisa.
While you’re in Pisa visit the famous Leaning Tower and the Cattedrale di Pisa, and enjoy the great shopping in the city center. After a few hours of exploring take a train back to Florence to enjoy your final night there.
>> Read: Florence to Pisa day trip
Day 7-8: Cinque Terre OR Venice
On day 7, take another 2 hour train from Florence to the five colorful villages of Cinque Terre. Make sure to check the times of the trains and book one with one change, because the trip can take much longer otherwise.
While you’re in Cinque Terre you can hike between the villages and experience the unique character of each of them. You can also take a boat through this part of the Italian Riviera to admire the fishing villages from another perspective.
Note: Book 2 nights in your Cinque Terre accommodation in order to get a feel for all five quaint towns.
>> Read more: The Ultimate Guide to visiting Cinque Terre
Note: We absolutely love Cinque Terre, but if you’d rather visit Venice you can swap Cinque Terre for Venice in this itinerary. Since Venice is easy to access via train from Florence, everything else in the itinerary can remain the same.
Day 9: Begin Tuscany road trip in Greve
During day 9 you will start your road trip through the most romantic and beautiful parts of Italy, Tuscany!
Logistics to begin your Tuscany Road Trip
While this day includes a bit of logistics, the destination is absolutely worth it! You will want to be in the Chianti region by noon, so this plan works backwards from there.
First, start your day early by taking the first fast train from Cinque Terre back to Florence (usually around 6:30 am). Then either take the T2 bus or a taxi to the Florence airport where you will pick up your rental car. After that you are ready to begin your Tuscany road trip!
>> Read: How to rent a car in Florence
Part 1 of your Tuscany road trip
Once you have your car drive to Greve, which is located in the Chianti wine region. Since you’ve already had quite the travel day, this first part of your Tuscany road trip will only take 45 minutes.
>> Read: Tips for driving in Italy
While you’re in Greve enjoy some wine tastings, go on a biking tour, visit the medieval towns and castles and take an authentic Italian cooking class.
In order to experience the classic Tuscan experience, spend your first night in a quaint BnB in Greve. We certainly fell in love with our stay at Cascina Dè Fagiolari where we stayed amidst the rolling hills and took the most incredible cooking class.
>> More details for a Tuscany Road Trip
Day 10: Tuscany road trip to Siena, Asciano & Saturnia
During your 10th day be prepared for gorgeous scenery, iconic hilltop towns and breathtaking natural hot springs. This is part two of your epic Tuscany road trip.
Wake up and enjoy your breakfast, and after that get on the road for your 1 hour drive to Siena. Certainly spend a few hours wandering the cobblestone streets of this medieval city. While you’re in Siena you have to visit the Duomo di Siena and the Piazza del Campo.
After enjoying the history and landmarks of Siena, continue your drive another 40 minutes through the rolling hills to Asciano. In order to get the best photo and view of Asciano, head towards Agriturismo Baccoleno and take the short walking trail here.
Finally, drive your last 2 hours to Saturnia, the most enchanting place in Italy. You’ll end your day relaxing in the magical hot springs of Terme di Saturnia and stay overnight in Saturnia. Here is the BnB we stayed in.
>> Read: Ultimate Guide to visiting Saturnia Hot Springs
Day 11: Saturnia to Rome to Positano
On day 11 you will start your journey to the stunning Amalfi Coast. While you’re in Saturnia, definitely take advantage of the thermal baths one final time before getting back on the road. After that, drive 2 hours to the Rome airport and drop off your rental car. (Note that because of this route you will be picking up and dropping off your rental car at different locations.)
Once you drop the car off, you have a couple options for how to get to Positano. You can book all of the trains and buses here.
- 1st option: take a train from Rome airport to Naples Centrale, and then a bus from Naples Centrale to Positano (cheapest)
- 2nd option: hire a private driver to take you from Rome airport to Positano directly (fastest)
>> Read this for where to stay in Positano and then book 3 nights in your Positano accommodation.
Day 12-13: Positano, Amalfi Coast & Capri
Finally on days 12 and 13 you can bask in the beauty of the Amalfi Coast. During your time here you can explore Positano, Amalfi and the Isle of Capri, and enjoy the Mediterranean Sea.
Whether you’re cruising the coast, boating, hiking, relaxing on the beach or taking the best Instagram photos, the Amalfi Coast is the perfect way to end your two weeks in Italy.
>> Plan your trip: 12 BEST things to do in Postiano, Amalfi Coast
Day 14: Fly home from Rome or Naples
On day 14 it’s unfortunately time to say goodbye to the country you’ve certainly fallen in love with by now. Start by reversing your route back to the Rome airport. Remember that this is a bit of a journey, so make sure to book a later flight and time your day accordingly.
Alternatively, you can take the bus from Positano to Naples and fly out of Naples.
Notes about this 2 week Italy itinerary
- For this itinerary you can book round-trip airline tickets from Rome
- If you aren’t comfortable renting a car in Florence you can limit your Tuscany days to just Siena because it’s easily accessed by train. To take this option, on day 9 catch a train from Cinque Terre to Siena and then get a train from Siena to Naples on day 11.
- If you have more time, consider adding more of the Best Places to Go in Italy to your itinerary!
2 weeks in Italy route map
Below is a map of the route for your 2 weeks in Italy. Click the ‘star’ next to the map name in order to save this map under “your places” in Google Maps.
Tips for your 2 weeks in Italy
- For a trip where you are moving between cities so much, be sure to pack light.
- The best time to visit the places on this itinerary is in the Summer. However, Italy gets exceptionally crowded in July and August so consider visiting in June or September.
Planning your trip to Italy? Make sure to check out all of our Italy Travel Blogs!
Enjoy your trip!
Kylie & Scott
(If you liked this article or have any questions, please comment below! And make sure to follow along on Instagram @LoveHardTravelOften)
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