Explore Tuscany: A 12-Day Road Trip Itinerary

An unforgettable Italian itinerary is a Tuscan road trip. Leaving Florence behind, you will navigate through winding two-lane roads that cut through beautiful hilly landscapes, connecting quaint hamlets, vineyards, farms, and ancient castles, all with numerous opportunities for spontaneous detours. Immerse yourself in the rural charm of the region, whether you choose to explore on two wheels or four.

Don’t forget your camera! Prepare to indulge in some of the region’s best gastronomic specialties during this 12-day adventure through Tuscany. This once-in-a-lifetime road trip takes you to world-class wineries, UNESCO World Heritage sites, and delightful farm stays that will leave lasting memories. Along the way, we provide varied detour options at each stop, allowing you to tailor this flexible itinerary to fit your preferences or follow it as it is.

Greve in Chianti: 2 Days

Distance: 50 minutes from Florence

After a few days in Florence, start your adventure by exploring the wine lands south of the city, traveling along the picturesque Via Chiantigiana. Set up base in one of the agriturismi (farm stays) near the medieval town of Greve in Chianti, and enjoy winery-hopping to taste some of Tuscany’s most celebrated wines.

Detour: On your way to Siena, don’t miss the fortified town of Monteriggioni, a historic gem along the Via Francigena (1 hour and 20 minutes).

Siena: 2 Days

Distance: 1 hour from Greve in Chianti

Siena offers a wealth of architectural gems. Spend a couple of days exploring the city’s highlights, starting at the iconic Piazza del Campo and the Palazzo Pubblico. Don’t forget to admire the remarkable Duomo and the vast collection of medieval art available in the city’s museums and cathedrals scattered throughout the historic center.

Detour: Make sure to visit the awe-inspiring Abbazia di San Galgano, a roofless Gothic abbey near Chiusdino (1 hour from central Siena).

Pienza and Val d’Orcia: 2 Days

Distance: 1 hour from Siena

Heading south towards the UNESCO-listed Val d’Orcia, enjoy the unique landscapes of Crete Senesi. Stop at the Abbazia di Monte Oliveto Maggiore before reaching Pienza, known as the “ideal Renaissance city” and a filming location from the original Gladiator film. Savor a plate of pici pasta (traditional Tuscan pasta) paired with pecorino cheese before continuing your exploration of the breathtaking landscapes and charming hamlets that make the Val d’Orcia iconic.

Detour: Don’t forget to capture a photo of the stunning Cappella della Madonna di Vitaleta between Pienza and San Quirico d’Orcia, a truly picturesque scene (30 minutes from Pienza).

Montalcino: 1 Day

Distance: 20 minutes from Val d’Orcia

As you depart from Val d’Orcia, make a stop in the fortified town of Montalcino, renowned for its famous Brunello di Montalcino wine. Visit the Tempio del Brunello and explore the nearby enotecas (wine bars) before heading to the countryside for a wine tasting experience at one of the region’s historic wineries.

Detour: Consider visiting the Abbazia di Sant’Antimo as you continue southward (1 hour and 30 minutes from Montalcino).

Città del Tufo and Pitigliano: 2 Days

Distance: 1 hour and 30 minutes from Montalcino

This segment features a road trip within a road trip. The southern reaches of Tuscany are known for their dramatic hamlets perched atop tuff-rock formations, with deep historical roots dating back to Etruscan times. The Città del Tufo area uniquely blends remarkable archaeological sites with charming towns, all accessible via scenic winding roads. Explore towns like Sorano, Sovana, and Pitigliano – often referred to as “little Jerusalem” due to its historic Jewish community – and wander through ancient caves and necropolises from the Etruscan era.

Detour: Relax from the long journey with a rejuvenating dip in the thermal waters of Saturnia (1 hour and 20 minutes from Pitigliano).

Orbetello: 3 Days

Distance: 1 hour from Pitigliano

Wind down your journey with a relaxing retreat on Maremma’s coast. Explore the area’s pristine beaches and protected wildlife reserves near the charming town of Orbetello. If time permits, extend your adventure to uncover the hidden coves of Monte Argentario and take a ferry to Isola del Giglio for some well-deserved Mediterranean sunshine.

Detour: Before reaching the coast, make a brief stop at the Giardino dei Tarocchi, a whimsical garden featuring monumental sculptures.