Val D’Orcia Self 7 Days Road

difficulty level

Hard

Exp. level

Advanced

route type

Road

rec. perdiod

Sep-Jun

Located south of Siena, in southern Tuscany, the Val d’Orcia is renowned for its breathtaking landscapes featuring rolling hills, vineyards, cypress trees, and medieval villages. Declared a UNESCO World Heritage Site in 2004, the area is famous for its natural beauty and the production of prestigious wines such as Brunello di Montalcino and Nobile di Montepulciano. Rich in history, the Val d’Orcia boasts fascinating towns like Pienza, Montalcino, Montepulciano, and San Quirico d’Orcia, which highlight the region’s cultural and artistic significance over the centuries. Ideal for nature lovers, food enthusiasts, and history buffs, the Val d’Orcia offers a unique experience of immersion in Tuscan tradition.

Day 1: Bike assembly and saddle position 30 km, 600 m

In the morning, guests will arrive at Florence Airport, where the Slice Adventures staff will transfer them to the accommodation in Montepulciano, their base for the entire vacation. After settling into their rooms, lunch will be served. A professional mechanic will assist guests in unpacking and assembling their bikes or adjusting the position for those who have rented bikes. A short test ride will follow to ensure the bikes and saddle positions are properly adjusted.

Day 2: 85 km, 1569 m

Starting from Montepulciano, the route begins with a gentle descent into the surrounding countryside. After a few kilometers, you’ll reach Torrita di Siena, a picturesque medieval village with walls and towers. Cycling along peaceful roads, you’ll enjoy views of green hills, olive groves, and vineyards that color the Crete Senesi landscape. Next, the route continues to Chianciano Terme, famous for its thermal baths and healing waters. Situated on a hilltop, Chianciano offers stunning views of the surrounding valleys. The journey proceeds to Monticchiello, a charming medieval village known for its ancient walls and open-air theater. The roads leading to Monticchiello feature gentle climbs and scenic descents, providing an immersive experience in the Tuscan landscape. Return to Montepulciano in the evening.

Day 3: 74 km, 1569 m

The day begins with a visit to Monticchiello, followed by a ride to San Quirico d’Orcia, a historic Tuscan village rich in artistic and cultural heritage. Highlights include the Collegiata di San Quirico e Giulitta and the Horti Leonini Italian Gardens. Next, the route leads to Torrenieri, a tranquil village overlooking the Val d’Orcia, before continuing to Montisi, a medieval gem with stone houses and narrow streets that evoke a journey back in time. Finally, visit Trequanda, an enchanting village perched on a hill offering spectacular views of the surrounding valleys.

Day 4: Rest Day

Cooking class and/or guided tour of the San Casciano dei Bagni archaeological site, followed by dinner in San Casciano.

Day 5: 93 km, 1830 m

The route begins with a visit to Pienza, a UNESCO World Heritage Site and a gem of Renaissance architecture. Known as the “ideal city” envisioned by Pope Pius II, Pienza is famous for its charming streets and Pecorino cheese. The ride continues to San Quirico d’Orcia, offering stunning views of cypress trees and rolling hills, before heading to Montalcino, renowned for its Brunello di Montalcino wine. Highlights include a visit to the Fortress of Montalcino and a wine tasting. The tour concludes with visits to Castelmuzio, a quiet medieval village, and a return ride to Montepulciano.

Day 6: 101 km, 2454 m

This is the most challenging route of the week, culminating in a climb to the summit of Monte Amiata. Begin with a visit to Chianciano Terme, followed by Sarteano, a medieval village with a castle, the Church of San Francesco, and Etruscan archaeological sites. Continue climbing to Abbadia San Salvatore, located on the slopes of Monte Amiata, where you’ll find the historic Abbazia di San Salvatore. After descending, visit Castel del Piano, surrounded by olive groves and vineyards, and Seggiano, known for its panoramic views and chestnut woods. Return to Montepulciano by van from Castelnuovo dell’Abate.

Day 7: Bye Bye

Breakfast at the accommodation and transfer to Florence Airport.