The most beautiful villages in Tuscany to visit
To embrace the most authentic soul of Tuscany, there’s no better way than getting behind the wheel and driving along its winding roads, where every turn reveals a new postcard view. Forget trains and rigid schedules: the true Tuscan journey is a slow road trip, guided only by the desire to discover the next hilltop village. In this article, you’ll find our personal selection of the most beautiful villages in Tuscany to visit.
The timeless charm of Chianti Classico
Our journey begins in the beating heart of Tuscany: Chianti Classico. The key thread of this itinerary is the Strada Regionale 222, the Chiantigiana, a ribbon of asphalt winding through endless vineyards and hills dotted with olive trees.
The first essential stop is Greve in Chianti, the moral capital of the region. Don’t miss its distinctive triangular Piazza Matteotti, perfect for a gourmet break featuring local cured meats and a glass of Gallo Nero. Continue with a short detour to Montefioralle, a tiny medieval gem listed among I Borghi più Belli d’Italia (the Most Beautiful Villages of Italy). Its walls and narrow alleys, where time seems to have stopped, offer an intimate glimpse into Tuscan history.
Towers in Valdelsa: the best Tuscan villages for history lovers
Leaving behind Chianti’s flavors, we head toward the Valdelsa, where the majestic San Gimignano rises. Nicknamed the “Medieval Manhattan,” this UNESCO World Heritage village is instantly recognizable by its iconic towers. Park your car outside the walls and get ready to walk inside, the atmosphere is pure medieval magic.
Just a few kilometers away lies the austere beauty of Volterra. This village boasts a history rooted in the Etruscan civilization, whose remains, along with Roman relics, lend the place a rugged and mysterious allure. It’s the perfect stop for a cultural break before heading south.
Val d’Orcia: postcard-perfect Tuscany
Now it’s time to travel the roads that made Tuscany famous worldwide we’re in the Val d’Orcia. Here, your car is your best companion, especially for driving along the scenic SP14 and SP146, which connect the area’s most iconic villages.
San Quirico d’Orcia is the ideal starting point: it sits at the heart of the landscape, surrounded by the famous clusters of cypress trees seen in countless photographs. From there, it’s a short drive to Pienza, the harmonious Renaissance “ideal city” and home of the renowned pecorino cheese. No itinerary is complete without visiting Montalcino and Montepulciano true temples for wine lovers where you can combine history with tastings of the prestigious Brunello and Vino Nobile.
The secret Maremma between tuff and the Tyrrhenian Sea
We conclude our journey through Tuscany’s most beautiful villages in the Maremma, a region offering dramatic and unexpected scenery. Here, three towns form the evocative “Città del Tufo” (Cities of Tuff).
The most spectacular is undoubtedly Pitigliano, perched atop a volcanic tuff cliff and breathtaking at sunset. Known as “Little Jerusalem” for its historic Jewish community, it’s a place steeped in history and mystery.
To finish in style, follow the Etruscan Coast to the charming Castagneto Carducci and the majestic cypress-lined avenue of Bolgheri, where the scent of wine mingles with the sea breeze.
Whether you’re after history, food and wine, or simply unforgettable landscapes, Tuscany by car will reward every kilometer you drive. All that’s left to do is fill up the tank and go rent a car from one of our Tuscany car rental locations and start your adventure!
