Tuscany is one of the most magical regions to experience in Italy! After many visits, we’ve created this 7 Day Tuscany Italy itinerary from Florence featuring some of the best towns along the way. From rolling vineyards and medieval villages to mind-blowing food, this Tuscany road trip in Italy will be one that you’ll never forget!
Planning Your Tuscany Italy Road Trip
🚗 The most ideal way to get around Tuscany is by renting a car. We always use this website to compare companies and deals around Italy.
☀️ Spring and fall are our favorite times of year to visit Tuscany. Spring is when the countryside starts to bloom with wildflowers and greenery, and fall when harvest season is in full swing. Here’s some fun Italy outfit ideas to pack for every season.
The crowds are one thing to watch out for in the summer, but the real reason to avoid this time of year is the intense heat! We saw this firsthand on our visit to Florence in August.
🍷 Something you might not realize is that you can’t just drop into every winery for a tasting. Once you know the route for your Tuscany Italy road trip, be sure to make a reservation in advance. Many vineyards also have have a small storefront where they do tastings in the closest town center.
💙 Make sure to always have travel insurance before your vacation. We’ve been using Safetywing for years and love how you can customize a plan based on your own needs.
🏨 Book your hotels in advance. Honestly, there are many options throughout Tuscany! Just know that in the summer and early fall the best accommodations will go quick.
This is especially true in the small villages where they might only have a couple of places to stay. We’ve added some of our own recommendations to each section of this Tuscany Italy itinerary.
Starting Your Tuscany Itinerary
The best way to begin your Tuscany road trip is by flying into a major city. We usually check Skyscanner first to find the cheapest prices and direct routes around our dates.
Florence is an easy choice as the capital of Tuscany! However, the train system is easy to use throughout the country. Don’t rule out starting from another major Italian city like Rome, and continuing onto Florence from there. Some travelers even start their trip at the leaning tower of Pisa!
There are often great deals on rental cars from the airport, especially if you book for a full week. Yet, it’s important to note that you won’t need a car for your time in the city. If you’re taking the bus or train in, then you can wait to grab your rental car somewhere locally on the day that you leave.
→ 12 Tips For Your First Italy Road Trip (And Mistakes to Avoid!)
7 Day Tuscany Italy Itinerary
2 nights in Florence
Florence is a city we can truly never get enough of! We’ve been all around Italy and end up here time and time again.
From the Duomo and incredible museums and all the delicious food, there are so many fun things to do in Florence! We recommend at least two nights here.
This is not only because it deserves more than one day, but you may need to recover from jet lag before your Tuscany road trip if coming from the United States.
Try and book your hotel somewhere around the Arno River and old town area. Hotel Berchielli is a good location to give you an idea.
This way you can walk to all the attractions that we’ve listed below. Also, make sure to book the major museums and sites in advance, as many of them require you to have a time slot for your visit.
- See the Statue of David and Galleria dell’accademia
- Explore the Duomo
- Climb Giotto’s Belltower
- Eat at Mercato Centrale and more amazing food markets
- Hit the Florence Wine Windows
- Visit Palazzo Pitti and the Boboli Gardens
- Experience Sunset in Florence at Piazzale Michelangelo
1 night in Cortona
Ready for the first stop on your 7 day Tuscany itinerary after Florence? Welcome to the beautiful town of Cortona. We first visited Cortona back in 2022 and instantly fell in love.
It will only take you about 1.5 hours to drive through the countryside from Florence. As with most places on our Tuscany Italy road trip, we recommend parking outside the town walls and walking everywhere.
Cortona has played an important part in the history of the region since the Etruscan and Roman times. In fact, it is nicknamed the “mother of Troy and grandmother of Rome” for the legends of Dardanus and Aeneas.
Even with all the incredible history, Cortona may be most well-known for it’s part in the movie “Under the Tuscan Sun.” Yes, you can even visit the Villa Bramasole and buy some olive oil as a souvenir!
Unlike some of the smaller villages on this Tuscany Itinerary, know that Cortona is quite large. We didn’t fully realize this until attempting to hike to the Fortress of Girifalco high above. It was well worth it for the views of town and Val di Chiana, but we wouldn’t recommend doing it in the peak summer heat!
You could easily spend more than one night strolling the historic streets and enjoying all the cafes and restaurants. Here’s a more detailed guide to the best things to do in Cortona, Italy. If you have time, you can even take a cooking class at a Tuscan villa.
Monastero Di Cortona Hotel & Spa is the perfect spot to stay if you’re looking for a bit of luxury. We also love Hotel San Michele, Hotel San Luca, and the apartment style rooms at Le Residenze Ristori.
2 nights in Montepulciano
Up for a quick stop in Umbria? The town of Castigliano del Lago sits right on Lake Trasimeno, and makes for the perfect place for breakfast or lunch en route to Montepulciano.
From there, it’s just another 30 minutes to Montepulciano, one of our favorite towns in all of Tuscany! We chose to spend two nights here on our Tuscany itinerary, as there’s just so much to see and do around the area.
It’s also nice to not switch to a different hotel each night, so you can have some time to relax and enjoy yourself. This is the heart of Tuscan wine country after all!
As soon as you enter the town walls, you’ll be greeted by several of the best Montepulciano wineries and their storefronts. This is a great place to taste wine, take an underground cellar tour, and buy some bottles to ship home.
Be prepared from here, as this town has some of the steepest medieval streets you’ll find on your Tuscany road trip! Don’t miss out on the local Thursday market, Piazza Grande, and walking to the San Biagio Church. The hike from Montepulciano to Montefollonico is a fun morning trip if you get the chance.
Check out Il Tosco and Via Di Gracciano for well-located accommodations or Palazzo Nobile di San Donato for an ultra-luxury stay. We also took an amazing day trip to Pienza, which is known as the ideal renaissance city for its unbelievable design.
→ 14 Fun Things to Do in Montepulciano Italy On Your First Visit
1 Night in Pitigliano
Once you’ve had your fill in Montepulciano, it’s time to move onto another stunning Tuscan village. Pitigliano is a place we’d seen pictures of, but could not truly understand the beauty until we arrived.
The walls of the town are perched high on a hill, looking out over the rolling green hills. This is another ancient Etruscan town with history dating back almost 3,000 years.
One of the best things to do in Pitigliano is to walk the vie cave routes to discover the paths of the Etruscans. The historic walking tracks are dug into the rock walls and have sunk even deeper over the years. This creates a feeling like you’re walking through an ancient tunnel, with tombs all around you.
Be sure to stop into the Jewish Quarter, where you can visit a 16th century Synagogue and museum. There is also a great local bakery just next door for a snack.
One of our favorite restaurants is Il Grottino. It overlooks the town and you can try a delicious wild boar ragu with wine!
B&B Dimor’à and Da Titta are nice places to stay right in the town center. Check out Maremma Nel Tufo to stay just outside of Pitigliano in a country house with a pool!
Another attraction that draws travelers to this area is the Saturnia Hot Springs. If you wake up bright and early the next morning, you could have it mostly to yourself before the crowds arrive.
1 Night in Siena
The last night of your Tuscany Italy itinerary may depend on if you have a flight out the next day. Siena is the perfect stop to complete this driving route on your way back to Florence.
While it is a city, Siena is small enough to explore in just one day. It is worth it to spend the night to stroll the medieval streets after many tourists have gone.
Grab a coffee in the gorgeous Piazza del Campo, see the 13th century Siena Cathedral (this is a great tour), and climb the 400 stone steps to the top of Torre del Mangia. If you’re visiting in the summer time, you may even catch the famous Palio de Senia horse race!
BnB Paolina and Casatorre dei Leoni Dimora Storica are located right in the historic centre, which is ideal for an overnight stay.
Finishing Your Tuscany Italy Itinerary
As you can imagine, one week in Tuscany is hardly enough time to see everything! This road trip will give you a small taste of villages, cities, and the unreal countryside.
The loop is a great way to save money on your rental car. Nevertheless, many travelers choose to start in Florence and finish in Rome (or vice versa). We went this way on our recent Tuscany Italy road trip and took the Rome to Barcelona ferry to get home to Spain.
If you’re considering heading to Rome afterwards, Porto Santo Stefano is a great overnight stop instead of staying in Rome. It’s just an hour from the Civitavecchia ferry port and 2 hours from Rome’s city center.
→ 10 Tuscany Italy Travel Tips For an Amazing Holiday
Have any questions on this article or want to share your own 7 day Tuscany Italy itinerary? Leave us a comment below!
Safe Travels,
Brigitte & Jake
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We’re Brigitte and Jake! American travel bloggers currently based in Spain. If you can believe it, we started Nothing Familiar way back in 2015 on an Ipad in the Ecuadorian jungle. Ever since, we haven’t stopped traveling! We’ve now been to over 60 countries around the world, with our expertise being Europe and Southeast Asia. We love outdoor adventures, tasting local specialties, and island hopping through tropical destinations. Hopefully, our guides and authentic experiences will inspire you on your own travels!
