Tuscan road trip: a flexible itinerary across the region's highlights

An Italian itinerary that can't be missed is a Tuscan road trip. As you leave Florence, twisting two-lane roads cut through hilly landscapes connecting stone-built hamlets, vineyards, farms and ancient castles, with an abundance of spontaneous detour opportunities. Leave art cities behind and embrace the rural character of the region on two or four wheels. 

Don’t forget your camera and prepare to taste some of the region's best gastronomic specialties on this 12-day itinerary through Tuscany. This road trip of a lifetime takes you to world-class wineries, World Heritage sites and farm stays you’ll struggle to leave. We've included detours at each stop, and since most towns are close to one another, you can tailor this flexible itinerary to your preferences or follow it as it is. 

This itinerary was adapted for the website from Lonely Planet's Florence and Tuscany Pocket guide, written by Angelo Zinna and Nicola Williams.

Greve in Chianti: 2 days

Distance: 50 minutes from Florence

After a few days in Florence, start exploring the wine lands south of the city, journeying through the Via Chiantigiana, the picturesque road connecting Florence with Siena. Set up base in one of the many agriturismi (farm stays) near the medieval town of Greve in Chianti and go winery-hopping to taste one of the products Tuscany is most proud of.

Detour: On your way to Siena stop at the fortified town of Monteriggioni, a historic stop on the Via Francigena (1 hour 20 minutes).

Siena: 2 days

Distance: 1 hour from Greve in Chianti

Architectural gems abound in the elegant city of Siena. Take a couple of days to explore the city’s attractions, starting with the sloping Piazza del Campo and its Palazzo Pubblico. Admire Duomo’s incredible pavement and enjoy the wealth of medieval art exhibited in the museums and cathedrals dotting the historic center of the former city-state.

Detour: Visit the incredible Abbazia di San Galgano, a Gothic roofless abbey near Chiusdino (1 hour from central Siena).

Pienza and Val d'Orica: 2 days

Distance: 1 hour from Siena

As you drive south towards the UNESCO-listed Val d’Orcia through the lunar landscapes of the Crete Senesi area, make a brief stop at the Abbazia di Monte Oliveto Maggiore, before continuing to utopian Pienza, the "ideal Renaissance city" and filming location in the original Gladiator film. Refuel with a plate of pici pasta (traditional Tuscan pasta) and some pecorino cheese before further explorations of the picture-perfect landscapes and stone-built hamlets that have made the Val d’Orcia with its wheat field and ancient cypress trees iconic.

Detour: Make a photo stop at the hillside chapel Cappella della Madonna di Vitaleta, between Pienza and San Quirico d’Orcia. Arguably one of the most striking chapel scenes you'll ever see (30 minutes from Pienza).

Montalcino: 1 day

Distance: 20 minutes from Val d'Orica

As you leave the Val d’Orcia behind, stop in the fortified town of Montalcino, the hilltop settlement home of the famed Brunello di Montalcino wine. Visit the Tempio del Brunello and surrounding enotecas (wine bars) before heading to the countryside for a tasting at one of the area's historic wineries, such as Ciacci Piccolomini D'Aragona or Fattoria dei Barbi.

Detour: The Abbazia di Sant'Antimo is a worthy stop as you continue further south (1 hour and 30 minutes from Montalcino via Abbazia di Sant’Antimo).

Città del Tufo and Pitigliano: 2 days

Distance: 1 hour and 30 minutes from Montalcino

This leg is a road trip within a road trip. Tuscany’s deep south is known for its towering hamlets built on tuff-rock formations inhabited since Etruscan times. The Città del Tufo area combines astounding archaeological sites with charming towns connected by twisting roads. Tour Sorano, Sovana and Pitigliano – also known as "little Jerusalem" due to the Jewish population that once lived here – and walk through the Etruscan-era caves and necropolises.

Detour: Recover from the long drive with a dip in the thermal waters of the spa town of Saturnia (1 hour and 20 minutes from Pitigliano).

Orbetello: 3 days

Distance: 1 hour from Pitigliano

Conclude your journey with a restful break on Maremma’s coast, exploring wild beaches and protected wildlife reserves near the seaside town of Orbetello. If time allows, extend your trip to tour the hidden coves of Monte Argentario and hop on the ferry to reach Isola del Giglio for a well-earned dose of Mediterranean sunshine.

Detour: Before reaching the coast, visit the Giardino dei Tarocchi, a quirky garden with monumental sculptures.