Nestled in the heart of Italy, Tuscany beckons with its enchanting landscapes, rich history, and amazing culinary delights. This picturesque region is a dream destination for travelers seeking a taste of la dolce vita, and what better way to explore its hidden treasures than by embarking on a road trip? Let us take you on a journey through the four most scenic road trips through Tuscany. Get ready to rev up your engines, as we venture into this land of rolling hills, vineyards, charming villages, and awe-inspiring panoramas.
Chianti Wine Route (SR222)
Florence to Siena : 72 km (45 miles)
A must for wine lovers, this route takes you through the most famous wine producing area in Tuscany. Beginning in Florence you will head south on SR222 and pass through beautiful towns such as Greve in Chianti and historic sights like the Verrazzano Castle. Stop along the way at charming wineries and sample the world famous Chianti wines. Arrive at your final destination, Siena, a city whose beauty could rival Florence with its medieval streets and ornate Duomo.
To read more incredible things to do and see in Florence, be sure to check out our Ultimate Florence Travel Guide.
Val d’Orcia
Montepulciano to Montalcino via SS 146 : 42 km (26 miles)
A UNESCO World Heritage Site, Val d’Orcia offers arguably Tuscany’s most breathtaking landscapes. Starting in the beautiful town of Montepulciano, drive south passing through iconic Tuscan villages such as Pienza and Belvedere di San Quirico before arriving in Montalcino in time to savor a glass of Brunello wine. Be sure to take your time and stop along the way to take pictures, as this road trip through Tuscany is just as beautiful as the destination.
San Gimignano Loop
San Gimignano Loop : 24 km (15 miles)
Start this road trip in the hilltop village of San Gimignano, famous for its imposing medieval towers. The Strada del Vino Vernaccia di San Gimignano is a short but stunning loop through the surrounding Tuscan hills. From afar you will truly appreciate the town’s iconic towers rising tall from the rolling hills, surrounded by vineyards and olive groves. After returning to San Gimignano, explore the historic town center and enjoy the local Vernaccia wine.
Crete Senesi
Asciano to San Giovanni d’Asso via SP 438 : 32 km (20 miles)
Crete Senesi, known as the desert of Tuscany, is a drive through this unique, yet captivating landscape. Starting in Asciano, admire the isolated farm houses dotted amongst rolling clay hills. The stark beauty of Crete Senesi is unlike any other you will see in Tuscany as you make your way to your final destination San Giovanni d’Asso. Here you will experience the town’s medieval charm and gastronomic delights, as the town proudly hosts a yearly truffle festival. This road trip through Tuscany is the perfect off the beaten path experience.
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