Welcome to Tuscany.

Kick off your adventure in the stunning Orcia Valley, nestled in the heart of Tuscany. Stay in the delightful hilltop towns of San Quirico d'Orcia or Pienza. Upon arrival, participate in a welcome briefing at the hotel, where our group will convene to outline the exciting itinerary and prepare for the days ahead.

Meet and greet your super guide.

Breakfast.

After breakfast, set off on a circular ride through the breathtaking Orcia Valley. Begin your journey from Pienza and San Quirico d'Orcia, and cycle to the picturesque wine town of Montepulciano, renowned for its Vino Nobile. Continue your ride to the medieval village of Monticchiello and visit the famous thermal spa of Bagno Vignoni before returning to your hotel.

• Distance Covered: 35mi (56km)
• Ascent: 2,969ft (905m)
• Descent: 2,969ft (905m)

Breakfast.

Experience a scenic cycling adventure through picturesque Tuscany. Start in San Quirico and ride along back roads to the renowned wine town of Montalcino. Descend to Buonconvento, then ascend to the charming walled town of Murlo, passing through Bibbiano.

From Murlo, tackle the short but steep Rospatoio Pass and enjoy a beautiful ride via Ville di Corsano. Conclude your journey in the splendid Gothic city of Siena, making this an unforgettable cycling day.

Breakfast.

Free day in Siena to immerse yourself in one of Italy's best-preserved medieval towns. Home to the grand Piazza del Campo, Siena offers a wealth of sights best explored on foot, despite its hilly terrain. Visit the stunning Duomo (cathedral) and numerous museums and historic buildings. Alternatively, opt for an unguided ride through the scenic surroundings. Whether you choose to explore or relax, Siena promises a memorable experience.

Breakfast.

From Siena, cycle directly into the heart of Chianti, exploring picturesque villages and stunning landscapes. The route takes you through beautiful hamlets and past spectacular vineyards and castles, including Castello di Brolio, where you can taste some of the finest regional wines.

Continue to Gaiole for lunch and enjoy a gelato stop in Radda before completing the final section to Castellina in Chianti, where you'll stay for two nights.

• Distance Covered: 32mi (51km)
• Ascent: 3,307ft (1,008m)
• Descent: 2,405ft (733m)

Breakfast.

Start your journey from Castellina and cycle through the rolling Chianti countryside, enjoying a scenic descent into the lower valley. From Poggibonsi, head towards the iconic towers of San Gimignano, a UNESCO-recognized town famed for its medieval architecture, Vernaccia wine, and saffron.

Spend a few hours soaking in the atmosphere, strolling along the ancient walls, and admiring the impressive towers. The return journey features a long but picturesque climb back to Castellina, where you can reward yourself with a well-deserved gelato.

• Distance Covered: 47mi (75km)
• Ascent: 3,957ft (1,206m)
• Descent: 3,957ft (1,206m)

Breakfast.

Cycle to Florence via Panzano and Greve in Chianti

Experience the final leg of your journey through the stunning Tuscan countryside, cycling from Panzano to the vibrant market town of Greve in Chianti. This route, considered one of the most scenic roads in Tuscany, links Florence to Siena via the picturesque Chianti hills.

Upon arriving in Greve in Chianti, take time to admire the triangular piazza that hosts the famous Chianti wine festival. Continue your ride towards Strada and Impruneta, known for their terracotta production, and stop for lunch in Impruneta.

Finish your ride by taking a panoramic road towards Florence, cycling all the way to Piazzale Michelangelo. Arrive in Florence in the early afternoon, allowing you to start exploring this magnificent Renaissance city. Visit the cathedral, the Baptistery of Saint John, and the iconic Ponte Vecchio, a medieval stone bridge lined with jewelers.

• Distance Covered: 32mi (51km)
• Ascent: 2,356ft (718m)
• Descent: 4,012ft (1,223m)

Breakfast.

Your cycling adventure concludes in Florence after breakfast. If you’d like to extend your stay and explore more of this magnificent city, please let us know. We can assist with additional accommodations and activities to make the most of your time in Florence.