Val D’Orcia Self 7 Days Gravel

difficulty level

Hard

Exp. level

Advanced

route type

Gravel

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 28 km, 750 m

In the morning, guests will arrive at Florence or Pisa Airport, where the Slice Adventures staff will transfer them to the villa in Siena, their base for the entire vacation. After settling into their rooms, lunch will be served. Later, a professional mechanic will assist guests in unpacking and assembling their bikes or adjusting the position for those who have rented bikes. Once everyone is ready, a test ride will be conducted to check the bikes and ensure everyone’s saddle position is properly adjusted.

Day 2: 67 km, 2000 m

This gravel route departing from Montepulciano is an exciting adventure through the Tuscan hills, perfect for outdoor enthusiasts and lovers of natural beauty. The journey begins with a visit to Monticchiello, a charming medieval village, before continuing to Castiglioncello del Trinoro, where breathtaking views await. After a rewarding climb, the route descends to Sarteano, known for its historic castle and picturesque center. From Sarteano, the ride proceeds to Chianciano Terme, renowned for its thermal waters, before returning to Montepulciano. With a mix of gravel roads, vineyards, and medieval villages, this itinerary offers a perfect combination of nature, sport, and culture for an unforgettable experience in the Tuscan countryside.

Day 3: 76 km, 2470 m

Starting from Montepulciano, this gravel route takes you through the stunning Val d’Orcia, one of the most beautiful regions in Tuscany. After leaving Montepulciano, the ride heads to Pienza, a UNESCO World Heritage Site, celebrated for its historic center and panoramic views of the surrounding countryside. From there, the journey continues along white gravel roads and trails immersed in nature, reaching San Quirico d’Orcia, another enchanting medieval village known for its gardens and historic streets. The route concludes with a return to Montepulciano, passing through breathtaking landscapes, vineyards, and rolling hills, offering a perfect blend of nature, history, and culture.

Day 4: Rest Day

Guided tour of the San Casciano archaeological site, followed by dinner in the city center.

Day 5: 84 km, 2140 m

Departing from Montepulciano, this captivating gravel route guides you through stunning landscapes of rolling hills and historic villages. The ride begins toward Cetona, a small medieval gem surrounded by unspoiled nature. The route then continues to Radicofani, where the medieval castle towers above the valley, offering unparalleled views of the Tuscan countryside. The itinerary alternates between gravel roads and asphalt, weaving through green landscapes, vineyards, and picturesque villages, before returning to Montepulciano. This adventure combines history, culture, and nature, offering an authentic Tuscan gravel experience.

Day 6: Torrenieri and Montalcino

Starting from Montepulciano, this scenic gravel route explores some of the most iconic locations in Val d’Orcia. The ride begins in Torrenieri, a tranquil village marking the gateway to Tuscany’s rolling hills. From there, the route leads to Montalcino, famous for its Brunello wine and the medieval castle overlooking the valley. The route alternates between white gravel roads and asphalt, offering breathtaking views of vineyards, cypress trees, and gentle hills. After exploring Montalcino, the return to Montepulciano provides spectacular vistas, completing an adventure that combines nature, history, and winemaking traditions.

Day 7: Bye Bye

Breakfast at the accommodation and transfer by van to the airport.