If you want to experience small town or village Italy, a Tuscany road trip should be part of your itinerary. After spending one night in Siena in 2017, we fell in love with the smaller towns in Tuscany. I started researching the area in earnest, and I realized that if we truly wanted to experience it, we needed to rent a car and we would need to stay in Tuscany, rather than trying to make day trips from Florence.
Tom and I debated the merits of a road trip for awhile, but I finally convinced him that it was the right thing to do to get the most out of the trip. He was most influenced by videos of the rolling hills and the Tuscan countryside. Once we picked up an International Driving Permit at our local AAA office for less than $30, we were set!
Our first road trip in Italy took us from Rome to Cinque Terre to Tuscany and ending in Florence. The one way rental car saved us a lot of money and backtracking. The benefit of having a car is that you can travel on your own schedule, stop when you see a beautiful view (or Christmas market!), and get off the beaten track.
After our first Tuscan road trip, we were hooked and returned in the spring of 2018 and 2019. We took an extended winter vacation through Tuscany and Umbria in winter 2018 and a short trip over Thanksgiving 2019. Having taken multiple trips to the area, I can’t imagine trying to see all of Tuscany in one day from Rome or Florence. I suggest a trip to Tuscany with Florence or Rome, but find a home base in the area. You can take day trips from there, but the magic of Tuscany happens when the day trippers leave.
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Tuscany Road Trip Itinerary Ideas
One of the things we’ve realized through our road trips is that it makes sense to group towns together by region. The distance between the hill towns are generally pretty short, but travel time can be a bit slow. Embrace it. Enjoy it. The best way to do that? Don’t be driving around Tuscany in every direction.
You want to find a home base, explore the area, and move to another area and check out that area. Depending on where you fly in and out of, a one-way car rental can prevent back tracking. Most of our road trips through Tuscany and Umbria have started by picking up a car in Rome and dropping it off in Florence. From there we’ve taken trains to other destinations or flown longer distances from PSA, FLR, or BLQ.
Exploring the Val d’Orcia
- Montepulciano – a medieval town with steep walks, sweeping Tuscan views, and walkable wine tasting. Don’t miss the annual Christmas market that stretches from the Piazza Grande to the Fortress.
- Pienza – Relatively flat compared to Montepulciano, Pienza claims the title for the ideal Renaissance city. Make sure to try (and buy) pecorino cheese at La Taverna del Pecorino in the city center.
- Montalcino – This town is famous for the Brunello wine and you’ll find plenty of vinotecas and wineries for tasting! Remember, you’ll want to make appointments at wineries. (Read more about visiting wineries in Tuscany!)
- Bagno Vignoni – We haven’t made it to these thermal spas yet, but over a shared meal, an Italian insisted on making me a list of places to add to any Tuscan itinerary. Bagno Vignoni was at the top with stars. With an endorsement like that, don’t miss it.
For a self driving tour of Tuscany, make sure to pick up a copy of this Guide to the Hill Towns of Central Italy.
Visiting the Most Popular Towns in Tuscany
- Siena – A capital city in its own right, Siena is absolutely beautiful. (It is easily reachable by train, if you’re not up to the challenge of driving in Italy.) Highlights include the old city walls, numerous churches, and the best people watching in Tuscany. If you can’t visit for the Palio, I recommend taking a walking tour of Siena with a visit to a local contrada museum. Don’t Miss: The Siena Duomo and seeing the Piccolomini Library!
- San Gimignano – I’m biased towards San Gimignano because one of my favorite wineries is just outside of the old city walls. One of the things I love most about San Gimignano (beyond the winery) is the number of galleries with the old city. While it gets very busy during the middle of the day, I definitely think it’s worth a visit. Try & Buy: the white balsamic vinegar with saffron and bring some home as a souvenir! It’s delicious on meat! (This is the only place I’ve been able to find it.)
- Volterra – Volterra is amazing and not just because the sunsets are perhaps some of the most beautiful I’ve ever seen. This walled city sits high above the hills in Tuscany and offers commanding views of the countryside. There are even Etruscan and Roman ruins to see. Make sure to check out the art, including the alabaster workshops!
- Monteriggioni – If you love historic, walled cities, don’t miss the most well-preserved walled city in Tuscany.
Straddling the Border of Tuscany and Umbria
- Arezzo – Arezzo is packed with history, but one of my favorite things is its festive Christmas market. Other highlights in the area include organic wineries, Roman ruins, and numerous historical sites. It will be the longest drive from Borgo dei Conti, but it certainly warrants a visit.
- Cortona – Best known to Americans for its role in Under the Tuscan sun, Cortona offers sun-drenches squares, an annual arts festival, and plenty of Etruscan history. I love Cortona for its spa hotel and delicious restaurants!
- Assisi Assisi should be more than a day trip– While I believe , it’s easy to reach from Borgo dei Conti. Plan your trip around this incredible walking tour of Assisi, which includes visits to many of the churches, including the Basilica of St. Francis.
- Montefalco – This was the biggest surprise of our Tuscany road trip. This charming, walled city caught us completely off-guard on a chilly winter evening. Montefalco wasn’t on our radar at all, but it is a necessary stop for any gourmet traveler. The wine and the truffles (when in season) shouldn’t be missed. (I especially recommend scheduling a visit to the Bocale winery.) Practice your Italian before you go.
If you’re looking for a quieter, more remote home base, I love Borgo dei Conti, nestled in the quiet hills of Umbria. From this resort, you’ll be able to explore the southern part of Tuscany and parts of Umbria with ease.
Tuscany Road Trip Inspiration
Things to Do in Tuscany
When I first started thinking about planning a trip to Tuscany, I wasn’t sure what we would do. We love tours and museums (and UNESCO World Heritage Sites), and I didn’t know what we would in Tuscany. I started doing some research and Heather’s post about the Top 10 Things to Do in Tuscany resonated with me. Loudly. The idea of relaxing, enjoying food and wine, and taking cooking classes sounded delightfully.
Best Places to Visit in Tuscany
Since we had already been to Siena, I wanted to find some new places to explore. Sarah’s post about where to go in Tuscany gave me a jumping off point to start my research.
I also loved Maggie’s one week Tuscany itinerary and would use it for inspiration on future trips. Maggie’s itinerary is great if you want to include Florence in your itinerary. (I love Florence so much that it has to be an independent part of any trip to Italy for us.)
Though we haven’t made it to Cortona yet, I loved this post on the reasons to visit Cortona. All of these reasons hold true for various places in Tuscany, so I think think it’s a great post if you’re on the fence about visiting the hill towns of Italy.
Where to Stay in Tuscany
Choosing a home base in Tuscany should be chosen in direct correlation of what you want to see without the crowds. For example, if you want to see the Leaning Tower of Pisa, you might consider staying in Pisa overnight. Staying in Pisa will allow you to get out early and stay out late, long after the day trippers have returned to Florence. If Pisa feels too touristy, consider Lucca. (Check out more about the hill towns of Tuscany or our favorite romantic hotels in Tuscany.)
One of our favorite towns is Montepulciano. We love Palazzo Carletti because of its beautiful rooms and free breakfast. Montepulciano feels “lived in” and we’ve had many memorable meals at Osteria Acquacheta. It’s a great location for exploring Pienza and Montalcino, too. There are a lot of places within walking distance for wine tasting, beautiful views off the side of the city walls, but you also have the benefit of being able to have meals at the area agriturismo restaurants.
Another great base in Tuscany is Siena. While not nearly as large as Florence, it certainly has a Duomo that rivals Florence, in addition to quite a bit of shopping and things to see. (We love the Piccolomini Library frescos. Don’t miss them.) When we stay in Siena, we stay at La Terrazza sul Campo, a family-owned B&B with an incredible view of the campo.
Tuscany Hotel Bucket List
Relais & Chateaux have a number of hotels throughout Tuscany that are on my hotel bucket list. (One of my favorite places to unwind in Italy is at Borgo dei Conti on the border of Tuscany and Umbria.) I’m also intrigued by Borgo Pignano, thanks to Julia’s anniversary post and the most beautiful sunset in Volterra.
I really want to stay in Pienza at La Bandita (found via instagram) in the future. This hotel has a more chic and sleek decor, as opposed to the frescoed ceilings of our other favorite hotels in Tuscany. The views off the side of Pienza are some of my favorite in Tuscany. And, Buon Gusto gelato might be the best gelato in all of Italy.
Tuscany Food and Wine Inspiration
- Discovering Culinary Tuscany
- Visiting a Vineyard in Tuscany
- 10 Best Restaurants in Montepulciano
- 10 Best Restaurants in Tuscany
Eating in Tuscany is an absolute delight. Look for handwritten menus, seasonal ingredients, and don’t be afraid to ask locals for recommendations. (We also love picnics.) Make sure to check out some of my tips for eating in Italy to make the most of your culinary adventures.
If you love steak, book a table at Acquacheta as soon as you can. There are two seatings for lunch and two for dinner. Leave room for the pastas. They are just as delicious as the steak. (Let Guilio cook it how it’s meant to be cooked.)
Some of my favorite pastas have been at small family restaurants outside of the town centers. I adore Poderuccio outside Pienza and Sant’Angelo outside Montalcino. Go with the simple sauces and the regional specialties.
For gelato, you can’t visit Tuscany and miss Buon Gusto in Pienza. You won’t find the normal flavors at this gelateria. Ask for their opinion and try things that wouldn’t normally try. Two of my most unexpected favorites? Saffron and Kiwi-Pear-Spinach.
Tips for Road Trips in Tuscany
- Scenic Drives in Tuscany
- Planning a Road Trip through Tuscany and Umbria
- Must See Towns and Things to Do in Tuscany
We travel with TEP or Skyroam (use JOURNEYOFDOING for 10% off!) so we don’t have to worry about our data plan or downloading google maps. This is especially helpful when you are on the smaller roads in Tuscany. It’s also helpful to have at least one book because you never know how reliable the internet will be. Better safe than sorry! You can see more of our driving in Tuscany tips if you’re curious.
Truthfully, a lot of our time will be spent enjoying the views. When we spent part of our honeymoon in Ireland, my husband mapped out routes that included seeing the sites and enjoying the countryside. When we are in Tuscany, you’ll see us slow down and enjoy a slower pace. I always look forward to sitting in piazzas (with wine), taking my own evening passigiata around a beautiful town, and capturing the beautiful Tuscan skies.
Listen, Learn, and Read More for your Tuscany Trip
- 25 Great Drives in Italy
- 25 Great Drives in Tuscany and Umbria
- Back Roads Italy
- Back Roads in Northern and Central Italy
- 10 Best – Florence and Tuscany
- Florence and Tuscany – Day by Day
- DK Florence & Tuscany
I highly recommend checking out these books because they break down different regions into manageable drives and include information on where to stay, restaurants to try, and what to see in the area. The back roads books include a lot of information and are really well made. I purchased them a few years ago and I’m excited to explore the recommended drives!
If you have suggestions or experiences to share, leave them below!! I’m always excited to hear more ideas!
Our Tuscany Travel Tips