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By Josie Hough - 5 min read

Tuscany road trip: 5 charming medieval towns

Tuscany road trip: 5 charming medieval towns

There are many, many excellent reasons to visit Tuscany. Art, culture, food, wine, beautiful natural landscapes, thousands of years of history… the list goes on. And as one of the largest Italian regions with attractions spread far and wide, the best way to make the most of this spectacular destination is a Tuscany road trip.

After planning your weekend in Florence and day trip to Pisa – essential visits on any trip to Italy – it can be hard to pick where to stop on your Tuscany road trip. Keep reading for our guide to the region’s most charming medieval towns and villages so you can get inspired for your trip…


One of the most beautiful cities in Italy, Siena is perfect for travelers looking for a romantic Tuscany road trip stop with all the charm of Florence, minus the crowds. Before you reach the city itself, we recommend stopping to admire its unique skyline of beautiful red brick medieval buildings from the surrounding hills. Once you arrive, start your exploring in the majestic Piazza del Campo, the enormous shell-shaped square at the heart of Siena, and get lost in its labyrinth of streets.

Eat – at Taverna di San Giuseppe, a family-run restaurant beloved by locals and tourists housed in a building dating back to 1100. Its cellar dates back even further (think BC), and is filled with an impressive selection of Tuscan wines. Try the pinci, a local pasta specialty similar to spaghetti, and the tiramisu.

Sleep – in 5 star luxury (well deserved after all that road tripping) at the awe-inspiringly elegant Grand Hotel Continental in the heart of Siena. You’ll feel like Tuscan nobility.

Drink – at Liberamente Osteria at aperitivo hour. You’ll enjoy your drinks with a feast of typical Italian appetizers, which will keep you ordering more drinks…

Do – visit at the same time as the twice-yearly Il Palio, a dramatic horse race taking place in Piazza del Campo. Taking place in July and August, the affair has been virtually unchanged since the 14th century, giving you a trip back in time.

San Gimignano

One of Tuscany’s best-known medieval towns, San Gimignano is around 45 minutes’ drive northwest of Siena. A walled hill town, it’s particularly famous for its incredibly well-preserved towers, earning it the nickname the Town of Fine Towers. Like the rest of Tuscany, San Gimingano is also known for its wine and food, its star product being saffron. Taste the precious spice in the most delicious way with saffron gelato from world gelato champions Gelateria Dondoli.

Eat – authentic Tuscan cuisine with a Michelin star at Cum Quibis.

Sleep – in the historic heart of the city, in a room with a view of the Tuscan hills at Hotel la Cisterna.

Drink – on the panoramic terrace at Divinorum. Sip on excellent local wines while admiring the beautiful valleys around San Gimignano.

Do – climb to the top of the Torre Grossa. Built in 1300 and measuring 54 meters in height, it’s San Gimignano’s tallest tower and offers incomparable views over the town and surrounding landscapes. The 218 steps are well worth it!


Halfway between Siena and San Gimignano is the small, fortified citadel of Monteriggioni. Having served its purpose very well as a defensive fortress in the 800 years since it was built, exploring Monteriggioni feels very much like stepping back in time. Or, alternatively, into poetry, if you’ve read Dante’s Inferno, in which the town’s walls feature!

Eat – exquisite Tuscan cuisine sat under historic stone arches at Ristorante le Torri or on the pretty terrace of Antico Travaglio.

Sleep & Drink – in one of the seven unique rooms housed in an ancient palazzo at Rooms & Wine. As its name suggests, the bed and breakfast also does wine tastings in the Castle of Monteriggioni and at their vineyard just outside of Siena.

Do – coincide your trip with one of Italy’s oldest medieval festivals. Held annually in July, it brings history to life with music, theatre, banquets and more.


If you’ve read our blog revealing some of Europe’s most enchanting hidden gems, you may well recognize Saturnia. Its 3000-year-old thermal springs are the most famous natural spa in Italy and well worth a visit to relax your muscles on your Tuscany road trip.

Eat – modern twists on traditional Tuscan food. Overlooking Saturnia’s historic central piazza, I Due Cippi da Michele has been at the heart of the local food and wine scene since the 1970s.

Sleep – at a quaint little bed and breakfast called Villa Garden. Located just outside of the town center, it’s the perfect spot for a quiet escape with unforgettable views over the Tuscan hills.

Drink – indulgent cocktails at the super friendly Barakka Bar, located near the hot springs.

Do – visit the spa, duh. Whether you treat yourself to a massage, stay overnight or just enjoy the healing benefits of the natural hot springs, the Terme di Saturnia should be a bucket list essential on your road trip.


A 30-minute drive northeast of Pisa, you’ll find the ancient city of Lucca. As charming as any other medieval town on your Tuscany road trip, Lucca is unique in that its historic defensive city wall remains entirely intact. Home to over 100 churches and countless other stunning monuments, it’s a must-visit for lovers of history and architecture.

Eat – on Cantine Bernadini’s cute little terrace facing the Palazzo Bernadini. Their mission is to produce as much of their incredible Tuscan delicacies in their own kitchens as possible, including making their sausages from an ancient recipe.

Sleep – at Hotel Palazzo Alexander, a 12th century palazzo which also served as a girls’ boarding school in the 1400s. Comfortable rooms are decorated in true typical Italian style with frescoes and marble, and their tiny balconies offer the best views of the old town.

Drink – wine at Ciclo DiVino before heading on to one of Lucca’s many great cocktail bars, like the beautifully decorated Dal Bardo or Franklin 33.

Do – park your car outside the city center and head in on foot to do a walking tour or rent a bike to immerse yourself in the medieval streets of Lucca.

Find more inspiration for your Tuscany road trip

This is by no means an exhaustive list of the charming medieval towns to stop at on your Tuscany road trip. Cortona, Montepulciano, Volterra, Pitigliano… the list goes on! But it’s a great start in planning your travels to this beautiful region of Italy.

From boutique hotels in Rome to the most beautiful vineyards in Tuscany, find inspiration for more amazing places to eat, sleep, drink and visit on TWISPER, the social app with only positive and personal recommendations.

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About the author

Josie is a content creator at TWISPER. She loves traveling and writing about her experiences. Check out her top recommendations for places to eat, sleep and drink around the world on TWISPER!