In this one week itinerary, I’ll show you how to see the best of Tuscany on a 7-day road trip. There are so many beautiful places in Tuscany, so it can be quite difficult to narrow it down. This itinerary will start off in the Val d’Orcia (one my favorite areas of Tuscany) and travel north to Florence.
I’ve included where to stay, travel tips and restaurant recommendations along the way. All stops are marked with a Google Map at the end to help visualize the trip. After all, the journey is just as important as the destination on a road trip in Tuscany.
*This post was first published in 2016. After years of blogging and living in Italy, I finally updated it in February 2021. It contains affiliate links. Thank you for your support!*
When to visit Tuscany
Tuscany is most enjoyable during shoulder season. The months of May and September are simply gorgeous, but I’ve also enjoyed my stays there in June, July and November. It’s hard to predict what crowds will be like once we are able to travel, but summers are known for being busy and very hot. However, if it is easier for your schedule to travel at that time and you’ve got your eyes set on lazy days by the pool in a villa, summer will fit the bill.
Sunflower season starts in June and can last into July. This is really a wonderful time to plan your trip if you’re not too deterred by the summer heat.
I have been to Tuscany in winter, and while it was still lovely, I would avoid January through March as many restaurants and shops are closed.
How many days do you need in Tuscany?
You really need a whole week to see a good chunk of Tuscany. However, if you can stay longer, this itinerary can be extended to two weeks by adding on days in Lucca, Cinque Terre and Rome. Want to do a grand tour? Consider adding on to this 10-day Northern Italy itinerary.
Route suggestions and Transportation
The best way to see Tuscany is certainly by car. Public transportation is great between cities, but to really see the small hilltop towns you will need the flexibility of a car. Rome has a large international airport, but you could also fly into Florence depending on your departure city and budget.
For this itinerary, you will start in Rome and end in Florence. You can always drop the car in Florence at the end of the week and take the train back to Rome. Depending on your jet lag, you might also want to consider staying a night in Orvieto on the way up (about an hour and a half drive).
Towns in Tuscany usually have a parking lot on the outskirts. The smaller roads within the center are reserved for residents. Even if they are not access restricted, they can be quite narrow and difficult to navigate. I am not ashamed to say I’ve encountered a few unexpected dead ends that required a nineteen point turn to get out.
You’ll definitely want to read the rest of my tips for driving in Italy before embarking on a road trip in Tuscany.
What’s the best base for a road trip in Tuscany?
Personally, I like to split time between two bases. A more rural choice and something located in town so I can have two different, yet equally wonderful experiences. Consider staying half of your nights in Southern Tuscany and half north near or in Florence.
Changing hotels more than twice can become a hassle to unpack. Using this itinerary, you shouldn’t have to drive more than about an hour between towns depending on your exact accommodation.
If you are going in a group with kids and know you would prefer to spend most of your time in a villa, relaxing by the pool, then go ahead and book a villa for the whole time. Choose somewhere more central like Siena (my husband AKA Medium Suitcase’s favorite place in Tuscany), giving you lots of easy day trip options and public transportation access to Florence city center.
Where to Stay in Tuscany
I am constantly saving hotels, villas and special properties in my google maps (read more about my general tips on how to plan a trip to Italy). I probably have over 100 saved in Italy alone, but here are a few I have been to or will be booking for next time.
Borgo Pignano is a classic luxury choice. I don’t know if it’s the view or the stonework, but there is just something about that pool that makes it easy to imagine spending several days there. Choose between rooms, suites, spacious marionettes and private villas.
Lupaia is a historic villa dating back to 1622 with beautifully decorated suites and rooms, each having a private entrance and access to the outdoor oasis.
A family friend of mine has a villa in Cortona and raves about Villa di Piazzano, a small luxury hotel dating back to the early 1500s.
As you head north, check into a property in or around Florence. You might have seen photos of the Loggia roof bar over looking Piazza Santo Spirito, but you can also book a night at its Hotel Palazzo Guadagni.
Villa Medicea di Lilliano is the perfect choice for a countryside escape while still being just a 20 minute drive from Florence. This property offers a number of different accommodations like spacious suites or small villas with a full kitchen and living space.
Also read the best Airbnbs in Tuscany with a view.
7 Day Tuscan Road Trip Itinerary
Day 1: Pienza – Bagni Vignoni
With its stunning views and streets that literally smell like pecorino, Pienza is a true gem in Tuscany. You cannot miss the cathedral in the middle of town. Stop at Bar Il Casello for a cappuccino or aperitivo and a view like none other. Check out La Bandita Townhouse or Villa Pienza if you want to stay in Pienza.
You can’t leave Pienza without taking some local pecorino to go from Marusco e Maria. Real cheese enthusiasts should take the 15 minute drive to Podere Il Casale for a farm tour and cheese tasting.
From Pienza, continue about 25 minutes to reach the ancient thermal bath Bagni Vignoni for the afternoon. If you take the northern route on SP146, you’ll pass by the Chapel of the Madonna di Vitaleta in the distance on your left.
I have only been to Bagni Vignoni in the winter when most cafes and shops were closed. I’d imagine after winter hibernation, this small ancient town comes to life with people enjoying the sun and wine on the patios and admiring the roman baths.
Day 2: Montepulciano
To start the morning, have a cappuccino out on the back terrace of Caffè Poliziano. Montepulciano is full of shops selling local products and look out points with views of the rolling hills.
While all of Italy is known for high quality wine, Montepulciano is exceptional. There are renowned wineries all around Tuscany, but a few notable ones in the town of Montepulciano as well. Contucci, Gattavecchi and Talosa are all in the town itself.
Day 3: Cortona
If you have ever seen Under the Tuscan Sun, stopping in Cortona is non-negotiable. It is an incredibly charming hilltop town with views of the valley below. Stop in the Piazza della Repubblica for a spritz with views of the clocktower and the spot where Diana Lane sits down to write a postcard in the film.
Day 4: Siena
Stroll up to the Fortezza Medicea for views of Siena and visit the Cathedral.
For a caffé and pastry, stop at Bar Pasticceria Nannini or Gastronomia Morbidi. In the evening, have a relaxing glass of wine while people watching in Piazza del Campo.
I visited Siena the last weekend of May and was lucky enough to see a parade with flag throwers. If you want to visit Siena for an event, plan your visit on July 2nd or August 16th for the famous horse race. I chose to stay at Hotel Italia right outside the city center for its easy access to free street parking and pet friendly policy.
Day 5: San Gimignano – Florence
As you move north from Siena to Florence, stop in San Gimignano. The town is famous for its medieval towers. Do not leave San Gimignano without having the award-winning gelato from Gelateria Dondoli.
Arrive in Florence just in time for dinner and a stroll across the Ponte Vecchio.
Day 6: Florence
There are so many museums, sights, piazzas and restaurants in Florence. You will need at least two days to even make a dent. Visit the Uffizi Museum in the morning.
You will certainly be ready for lunch after walking around the museum. Have a panino at the famous Osteria All’antico Vinaio around the corner (expect a line) or snag a stool on the sidewalk at La Prosciutteria a few doors down.
Visit the leather school or see the statue of David at the Accademia in the afternoon. End the evening at Piazzale Michelangelo for incredible views of the sunset.
Day 7: Florence
Visit the Cathedral of Santa Maria del Fiore – Tickets are not required to access to the cathedral, but you do have purchase a ticket to visit the dome. If you want a workout after eating your weigh in pasta and cheese all week long (rightfully so), climb over 400 steps to the top. Consult the website for the most up to date information and opening times.
Have a coffee at Ditta Artigianale before you before you inevitably must pack your bags and say goodbye to this wonderful part of Italy.