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Tuscan road trip: a flexible itinerary across the region's highlights
30.09.2024 - 14:43 / lonelyplanet.com / Nicola Williams
Sep 30, 2024 • 4 min read
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.
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).
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).
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
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