The Best Tuscany Road Trip Itinerary: A Detailed 10 Days In Italy Itinerary

Suppose you’re searching for the ultimate Tuscany road trip itinerary, but you’re bored of reading about all the same places. In that case, I’ve created this unique 10-day itinerary that’s going to be perfect for you. 

We spent eight weeks driving around Italy, two of which were spent in Tuscany. So we know exactly where to visit and how!

I’ve filled it with our favourite stops, from the main cities of Florence and Siena to the smaller, lesser-known hilltop villages like San Gusme, Panzano, and Montefioralle. We’ll also be visiting my favourite Tuscan town, Pienza, plus many more!

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Uncover The Best Of Tuscany With My 10 Day Road Trip Itinerary In Italy

In this post, I’m sharing my 10-day Tuscany road trip itinerary. It’s a really detailed itinerary full of personal insights and travel tips. I’m also covering topics including:

• The best attractions at each place.
• Ideas on where to stay for either hotel or campers.
• Our favourite places to eat and drink. 
• Additional/alternate stops
• Practical information like tips for driving, driving time, and route maps.

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About This 10 Day Tuscany Road Trip Itinerary

Jack and I travelled to Tuscany on the first road trip in our self-converted Ford Transit last summer/autumn. It was an incredible experience, which we loved. We created so many beautiful memories, but driving around the Tuscan countryside was spectacular. 

There’s a reason it’s one of Italy’s most beloved regions, and once we got there, we were left in awe. It’s seriously beautiful, and the best way to experience it is on a 10-day Tuscany road trip. 

In this road trip itinerary, we’ll be travelling south from Florence through the Chianti Valley to south Tuscany before looping back around to visit Siena and San Gimignano before ending in Pisa.

For each location, I’ve included the must-visit attractions, tour recommendations, any hikes we did, where we stayed and a hotel suggestion for those of you not travelling in a campervan. 

⭐ Pro tip >> For those of you travelling in campervans, I recommend downloading the Park4Night App. It was really the only thing we used to find parking, and it works incredibly well. It’s a review app which notes all the campsites, car parks, farms, etc., where you can spend the night.

Are 10 Days Enough?

We actually spent a little longer than ten days and visited a few additional places, which I have noted below in case you can extend your trip. But overall, ten days are enough to get a feel for what Tuscany has to offer.

If I’m honest, this 10-day itinerary is quite packed, but we’re on a road trip after all; some of the villages in Tuscany only require an hour or so to visit, walk around and perhaps grab a coffee. I’m all about the views, and half of the adventure was driving through the valleys, vineyards and olive groves.

We also didn’t mind moving on every day. If you think this is going to be too much, consider extending your trip or removing a few destinations. The villages in the Chianti Valley are lovely, but they are pretty similar, so perhaps you could remove a few of these to free up some time.

Tuscany Road Trip Itinerary Map & Route

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Must-Visit Attractions

My favourite activity in Florence was climbing to the top of Giotto’s Bell Tower. We had planned for Brunelleschi’s Dome, but tickets had sold out. Keep this in mind if you plan to visit, and know you’ll need to book in advance. Included in the ticket is the entrance to the Opera del Duomo Museum, Baptistry and the Cathedral basement. The Cathedral is free to enter.

The best thing we did in Florence was join a food tour; it combined both a historical walking tour and local food tastings. It really was fantastic, and it allowed us to learn more about the city’s history and the typical cuisine of the region. 

Florence is a city to be explored on foot. The best thing you can do is wander around and enjoy the architecture, visit a museum and explore the markets. I don’t recommend visiting the Boboli Gardens; we’ve written a review here. They’re meant to be a top attraction in Florence, but Jack and I were not impressed. 

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Tuscany Road Trip: Montefioralle & Greve in Chianti (1 Day)

Montefioralle is one of those small villages I mentioned earlier; it’s actually really tiny and won’t take long to walk around. It’s a great addition to this road trip and the hilltop villages dotted throughout Tuscany with panoramic views. It’s the perfect place to grab breakfast or lunch.

Afterwards, you can head to Greve in Chianti. We stayed the night in Greve and so have recommended doing it this way around, but if you prefer, you could always visit Greve first and end your day in Montefioralle. There’s only a five-minute drive between the two. 

Greve in Chianti is a lovely town, with a nice piazza filled with cafes and restaurants. At the top of the plaza is a small church, which you’re free to wander around. We did spend an hour venturing further into the town, but in all honesty, there’s not much to see outside of the piazza and a small street lined with shops. 

⭐ Pro tip >> In general, shops open at around 9 am and close at 7 pm, but we noticed the smaller towns have shorter opening hours. Many shops close for a few hours during the afternoon, usually from 1 pm to 3:30 pm. Some restaurants remain open. Sundays and sometimes Mondays, they are closed all day.

Must-Visit Attractions

The highlight of Greve in Chianti is its Piazza Giacomo Matteotti. The plaza is home to the giant bronze statue of the great navigator Giovanni da Verrazzano and the perfect place to start a wine journey through the Chianti Classicos. I actually don’t like the Chianti Classico all too much, which is something I learned on this trip!

The shopping street is called Via Roma and connects to the Piazza Giacomo Matteotti. It has a handful of small boutique shops, perfect for purchasing some souvenirs, but don’t get carried away; it’s still early days, after all.

Another place we were amazed by and that you have to visit was Antica Macelleria Falorni. It’s a butcher shop deli famous for its cured meats. 

The shop is sort of a novelty, with shelves filled with salami and meats, legs of pork hanging overhead, old slicers, strong smells and even a Pecorini cave. We also entered a room showcasing their ageing process by using a traditional ash technique.

Where To Eat & Drink

• Montefioralle: You’ll want to visit Bar Cafe Montefioralle for breakfast or I’Desìo for lunch. In summer, it’s essential to make a booking for I’Desio.

• Greve in Chianti: We ate at Antica Macelleria Falorni Bistro. It’s got outdoor seating on the Piazza Giacomo Matteotti. I recommend the Cutting Board Di Stefano and purchase the Wine Card for tastings before ordering a bottle.
• Market Day: Every Saturday from 8 am to 1 pm.

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Must-Visit Attractions

In Castellina in Chianti, you can enjoy many beautiful sights, including a 14th-century fortress (Rocca), the 16th-century San Salvatore church and the arched passageway. Although we didn’t visit them, just outside of the town are two pre-Roman Etruscan burial tombs.

In Panzano, it’s the market. You can also pop into the Church of Saint Mary, which is near the parking. The panoramic views are superb. 

In both locations, you’ll be able to enjoy wine tasting, explore the town centres, and take in the beautiful scenery. There are also plenty of restaurants and cafes where you can sample local Tuscan cuisine. 

Where To Eat & Drink?

• Panzano: Pasta & Pizza was super affordable and delicious. We had a drink at Enoteca Baldi while sitting outside enjoying the market buzz.
• Markey Day: Every Sunday from 8 am to 1 pm

• Castellina in Chianti: Osteria Rosticceria Il Re Gallo is really good. You might need to make a reservation if you are visiting during peak season. Ristorante La Bottega del Borgo was also busy, and we enjoyed Il Cantuccio Wine Bar.

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Must-Visit Attractions

In Gaiole, there are not really any attractions that we noticed apart from a church at the top of the village: Chiesa di San Sigismondo. 

This is mostly a place to enjoy picturesque landscapes, medieval architecture, and, of course, its famous wineries, such as Castello di Brolio, which you’re visiting tomorrow!

Out of town is Badia Coltibuono, a Wine Resort & SPA producing their own wines. It’s a farmhouse in an ancient abbey and also a hotel. We didn’t visit, but I have heard good things, and it might be somewhere you want to consider adding to your itinerary.

Walking/Hiking Trails

There is a third village accessible from Gaiole in Chianti as well. If you want to do a full-day hike, there is a way to hike between the three villages: Gaiole in Chianti, Vertine and Barbischio, or you could even add Badia Coltibuono into the mix. However, for us, it would’ve been too far.

I recommend downloading the All Trails App – this is the Gaiole in Chianti to Vertine circuit we did. All Trails has loads of route maps for trails around the world, and there’s a free version, too. We used it a lot during our road trip, and it’s excellent for showing trails throughout Tuscany.

Our hike to Vertine took about one hour and a half. The village is cute but tiny, with panoramic views. In the end, we drove to Barbischio the morning before we left. There’s a single restaurant in this hilltop hamlet, which was closed when we arrived, but it would have made for a lovely dinner spot.  

Where To Eat & Drink?

• Lo Sfizio was our favourite as the staff were so friendly.
• Market Day: The second Monday of every month from 2 pm to 8 pm (except for September, which is the first Monday). 

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Must-Visit Attractions

Castello di Brolio is an attraction in itself. For €7, you can visit the castle independently and walk within the outer walls and around the gardens. You can’t really go inside the main castle; the only access permitted is the family chapel, crypts and a beautiful panoramic viewpoint. 

For €7, it’s worth it, though, and the ticket price includes a complimentary wine tasting in the Enoteca del Castello di Brolio Wine Shop. Guided tours are available for an additional price, which provides a more intimate visit to the castle. 

Across the road from Villa a Sesta is the Villa a Sesta Winery. This place is great and is definitely worth stopping for wine and olive oil tastings. 

⭐ Pro tip >> You could stop by Villa a Sesta on your way to San Gusmè, too. We did, but unfortunately, renovation works were happening, and the main piazza was a building site. Otherwise, it probably would have been quite lovely for a coffee. 

Where To Eat & Drink?

• Castello di Brolio: The barely-there village of La Madonna is at the bottom of the castle hill. Opposite the wine shop, there is a small cafe that is good for coffee and pastries in the morning called Agribar Brolio.

• San Gusmè: There isn’t much choice; when we visited, everything was closed. The only one I can find is Osteria Bruschetteria da Sira e Remino, a traditional Tuscan restaurant.

⭐ Pro tip >> In Italy, an osteria is a type of traditional eatery that serves simple, home-style meals and local wines in a casual setting. 

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Must-Visit Attractions

The old town is a must, and a visit to the Palazzo Piccolomini. On the main square, pop into the Cathedral of Santa Maria Assunta. The Palazzo Borgia Museum tributes to Romeo and Juliet, as the property was used for movie shooting. Don’t miss a sunset stroll along Via S. Caterina for unbelievable views.

Pienza is also celebrated for its pecorino cheese, which is made from the milk of sheep that graze on the surrounding hills. Be sure to sample and purchase this cheese at any one of the speciality shops throughout the town. 

Finally, stroll along Strada di Terrapille and snap a photo at the famous Gladiator filming location.

Walking/Hiking Trails

The Strada di Terrapille is the Campi Elisi walking trail. It will take you along a dirt road amidst the nature of the Val d’Orcia. From the centre of Pienza, it will take about 40 minutes one way.

The road is bumpy, downhill and not very shaded, so it’s essential to have comfortable shoes and sun protection. There are literally no amenities along the walk.

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Must-Visit Attractions

In Montalcino, there are plenty of things to do, such as visiting the medieval fortress and the Gothic-style cathedral. You can also take a stroll around the town’s walls for panoramic views of the surrounding countryside. 

Some of the must-visit places in Siena include the Piazza del Campo, which is one of the most beautiful squares in Italy. The Siena Cathedral is a stunning example of Gothic architecture. Visit Piccolomini Library and the Civic Museum inside the Palazzo Pubblico, which houses the famous frescoes of Ambrogio Lorenzetti. 

Siena is also known for its delicious cuisine, including dishes such as pici pasta, ribollita soup, and the famous Chianti wine. That said, Jack and I actually had one of the worst pasta dishes in our lives from a restaurant in Siena!

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Must-Visit Attractions

There are a bunch of attractions in San Gimignano, from the historic Piazza della Cisterna to the impressive Torre Grossa, which I recommend climbing to the top. The views from up there were incredible.

Visit the Museo Civico, the Cathedral (Duomo di Santa Maria Assunta) and the Palazzo Comunale to learn more about the town’s rich history. We even visited a torture museum, which was interesting.

We wandered around as there was plenty to see and explore. Be sure to explore the side streets and turn off the main shopping streets. Via Piandornella has beautiful panoramic views, and at Via Degli Innocenti, you’ll find some stone tunnels and archways.

We spent two days here, one being market day. It was a lot smaller than I expected, but there was a nice vibe. However, it’s not essential to visit the market, and actually, you might be better off visiting on a different day as it ruins the views of the central piazza.

If there’s one market I do recommend attending, it’s the one in Panzano. 

Where To Eat & Drink?

• Vinaio di San Gimignano: Right on the main piazza – exceptional sandwiches and cutting boards. Try the delicious white Vernaccia di San Gimignano. Plus, their beer prices are insanely low!
• Ricca Pizza on Via S. Matteo: It’s a great spot for pizza on the go.
• Gelateria Dondoli: Don’t miss the chance to taste some of the best gelato in Italy.
• Market Day: Every Thursday in the morning from 8 am to 1 pm.

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Tuscany Road Trip: Pisa (1 Day)

The final destination on this Tuscany road trip itinerary is Pisa. We really enjoyed Pisa even though we’ve heard a lot of people say it’s not worth visiting; I disagree. I think Pisa is worth visiting and has hidden gems ready to be discovered.

We spent (almost) the whole day and enjoyed visiting the attractions, strolling along the Arno River and ending our final night in Tuscany on a high. Since Pisa is a vibrant university town, it gives the city a lively, youthful atmosphere, with plenty of bars, cafes, and restaurants.

⭐ Pro tip >> I will say that Pisa should be visited on a Friday or Saturday – we were there on Friday. The atmosphere was cheerful, which is what we enjoyed the most, but during the week, it might be different. 

Must-Visit Attractions

The Square of Miracles is home to the iconic Leaning Tower and other important historical and cultural landmarks, including the Cathedral of Santa Maria Assunta and the Baptistery of San Giovanni.

When you’re visiting Pisa, it’s also worth taking the time to explore the city’s historic centre, which is filled with winding lanes, colourful buildings, and charming squares. There are also several museums and galleries in the city dedicated to everything from ancient Roman artefacts to contemporary art.

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Alternative/Additional Stops: 10+ Days In Tuscany

Aside from the stops I’ve listed above, there are a number of additional places you might be interested in visiting. To keep this to a 10-day Tuscany itinerary, consider switching locations along your road trip to fit in Montepulciano or Voletra if you prefer to visit these places. 

Both Cascate del Mulino and Monte Argentario are further west and require more time to visit. We spent a week beach hopping on the small peninsula, which was fantastic fun! Although we didn’t visit Cascate del Mulino (we read it was expensive when really it’s free), the photos look amazing. 

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In Summary: Tuscany Road Trip 10 Day Itinerary

This 10-day road trip itinerary is perfect for seeing the best of Tuscany and visiting some of my favourite destinations. However, if you’re thinking of skipping some, I’d suggest San Gusme, Castellina in Chianti and Montalcino or Siena. The others offer a unique experience into the heart of Tuscan tradition.

As always, I hope you have a great road trip and have found this Tuscany itinerary useful.

We really had an unforgettable adventure exploring the Tuscan countryside and medieval towns, and the vineyards were spectacular. However, I’m still undecided about whether I prefer Alsace’s wine route or the rolling hills of Tuscany. There is strong competition!