Last Updated on 04/27/2023
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 2021. It contains affiliate links. I was hosted as a guest at Antica Torre and Hotel Le Fontanelle. 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 larger cities, but to really see the small hilltop towns you will need the flexibility of a car. I used my own car for the majority of road trips in Italy, but I have also rented a car from RentalCars.com when I wanted a slightly more larger and reliable car than my Fiat.
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.
For the perfect balance of luxury and charm, book a stay at Hotel Le Fontanelle just 25 minutes from Siena. I love that this property is owned by a woman in her 90s. She lovingly restored the ruins with the help of her niece to be the luxury hotel it is today. Not only does the hotel offer a pool, 5-star restaurant, spacious suites and beautiful views, you can also easily visit the family winery next door owned by her brother.
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.
For unparalleled views of the duomo and the Arno river, check out Antica Torre located on a the designer shopping street in Florence.
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.
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.
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Hi Scarlett
We are planning a Italy road trip for 10 days for September 2025, which we are planning to drive ourself. We would like to to make sure we throw Rome and Pisa in with everything you suggested, could we get that all in 10 days? We want to see the wine country and all the beautiful land/towns. Rome is one of the special places that we want to visit because my Mother always wanted to see it but never had the chance to go. Our daughter-in-law told us that if we fly into Rome and make our way up north and end in Florence to turn the rental car in there and take the train back down to Rome to end our visit. Any suggestions would be appreciated.
Hi Lisa,
It is never too early to start planning! That would be a very rushed 10 days, in my opinion. I haven’t been to Pisa in forever, but I didn’t think it was that special honestly. It all depends on your style of travel, but I would suggest 3 days in Rome, 4 days in Tuscan countryside, 2 days in Florence and a travel day.
And yes, that is an excellent suggestion from your daughter-in-law. The train from Florence to Rome is fast and direct. Just be prepared that sometimes a rental car company can charge a one-way fee (sometimes it is reasonable, but other times it can vbe ridiculously expensive).
Let me know what you decide!
Kate – Thank you for the wonderful itinerary tips. We will be in Tuscany for 7 days in May 2023 and are looking for an apartment with full kitchen and 2 bedrooms. Do you have any to recommend? Appreciate your knowledge and help.
Hi Jan,
I haven’t stayed at any apartments with a kitchen, but I have heard good things about the apartments at Villa Cozzano and Villa Medicea di Lilliano.
May is a nice time to be in Tuscany. Enjoy your trip!
Name is Scarlett…. Not Kate ; )
Hi, we have just used your guide to book our trip in late May! We’re going for a week and staying just outside Pienza for 3 nights to visit Pienza, Montepulciano, Bagni vigorous & maybe Cortana. Then a night in Siena, a night in a winery a bit north (this wasn’t on your list but we had to squeeze in a winery stay!) then Florence. Thanks for the blog, it’s so helpful!!
Hi Emma,
Adding a winery stay sounds like a wonderful plan! I’d love to hear how it all went when you return. Enjoy your trip!!
Thanks so much for recommending Borgo Pignano and Lupaia. These 2 places absolutely made our trip to Tuscany unforgettable.
So glad to hear those hotels made your trip!
Gorgeous photos and great recommendations for a week in Tuscany.
Thank you so much for your informative and inspirational posts on Tuscany!
We will be there in October for a week.
Can you recommend accommodations in Montepulciano?
Thanks so much!
Hi, Scarlett, thinking of heading to Tuscany this September, hiring a car and visitng many of the places you have suggested here, which area would you suggest staying in Southern Tuscany as a base to explore the surrounding areas? Before heading North for a few nights in/around Florence. Also, myslef and my partner are big wine fans and would love to visit a couple of vineyards whilst there (white wine ideally), any recommendations.
Thanks so much for all the info
Hi Jules, September is my favorite time to visit Tuscany. Southern Tuscany is absolutely beautiful. I really like Pienza and Montepulciano (slightly closer to the freeway for easy day trips). You can’t go wrong with wine in this region. There are wineries everywhere that you are sure to enjoy.
Heading to Italy in 3 weeks (June 2022).
Itinerary Rome (3nights)-Florence(2)-Bologna(2)-Modena(1)-Venice(2).
Renting a car when we leave Rome and planning on driving and returning car @VCE. Having a difficult time deciding stop(s) between our longest trek…Rome- Florence. So many choices. We love wine, food etc. There are 4 of us. I’m overwhelmed by choices.
Hi Karen, That sounds like a wonderful itinerary! The road from Rome to Florence is filled with many gems. Orvieto and Montepulciano are two great stops not too far from the freeway. Enjoy your trip!
Hi Scarlett,
This is wonderful and very helpful post. My friend and I will be visiting Tuscany in spring of 2023. I did consider fall, but the days are so much shorter. We are considering staying in Villa a Sesta for maybe the entire 7 days and day doing trips from there. Is that feasible? How do we handle transportation for winery tours when we stay in a rural location especially in the Montepulciano area?
We will start our trip in Venice, and include Siena and Florence.
Thank you,
Kathy
Hi Kathy,
Honestly, I am not as familiar with the area around Villa a Sesta as I am with the Val d’Orcia area. It does seem centrally located though and feasible for day trips. Depending on your interests, you might want to think about splitting it up. Half in Florence and half more towards Montepulciano.
You could look into winery tours that offer transportation. Group tour and private drivers are available in the area.
Spring will be lovely. Have a nice trip!
How do you find private drivers?
I personally have never used a private driver in Tuscany because I lived there and had my own car. However, a quick search on google will find you companies that arrange drivers and tours. You can also look on Viator or Get Your Guide. Lastly, depending on your hotel, they could probably arrange one for you as well.
Love all your Italy posts they are the most helpful. We will be traveling to Italy this fall for the month of Icyobwr. I want to stay in the Tuscany area for a week have a rental car and just see as much as possible each day. About how many places can I see in this time by car? PS I may just skip bringing a camera and use my iPhone
Hi Toni, You can easily see a town or two a day if you have a car. You can also break it up (three nights in Southern Tuscany and three nights more north like Florence). iPhones take pretty amazing photos these days and are more than efficient for the everyday user. Enjoy your trip 🙂
Hi Scarlett, this is such a great post on Tuscany, thank you so much for sharing! My husband and I are going to Tuscany and I can’t wait! We’re thinking of going to Siena, Chianti, and Lucca – we’ve found it difficult to find good resources for tips, so I’m glad I stumbled upon this via pinterest! I really love your photos! What camera do you use?
Thanks again for sharing!
-Kate
Thank you Kate! You will love Tuscany. It is so beautiful! I’ve also heard great things about San Gimignano and its award winning gelato. I use a Canon Rebel T5 for my DSLR, but a lot of photos on my blog are taken with my iPhone too ; )
Don’t hesitate to reach out if you have any questions about the area!!
Ciao ciao!