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Siena Self 7 Days Gravel

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Siena is the ideal destination for cycling tourism, thanks to its perfect mix of breathtaking landscapes, medieval villages, and scenic roads. The Sienese territory offers countless routes suitable for both experienced cyclists and those looking for a relaxing ride. According to all our customers, what sets the Sienese area apart is the variety of landscapes found within a relatively small area. We can roughly divide the Sienese countryside into four main areas: Chianti to the north, the Crete Senesi to the southeast, the Val d’Orcia to the south, and the west of Siena extending to the upper Maremma. The Chianti region lies in the heart of Tuscany, between the cities of Florence, Siena, and Arezzo. The entire area is characterized by rugged hills, green landscapes covered with kilometers of vineyards and olive groves, medieval walls, and castles. The unique climate and soil make Chianti particularly suited for producing high-quality wines and oils. The region is also rich in castles, medieval villages, and wineries steeped in history and charm. The Crete Senesi are renowned for their striking and surreal landscapes. The clay hills, eroded by rain and wind over the centuries, create a fascinating panorama often compared to a lunar landscape. Declared a UNESCO World Heritage Site in 2004, the Val d’Orcia is known for its iconic views, featuring rolling hills, cypress trees, vineyards, and medieval villages. Must-visit spots include Pienza, Montalcino, San Quirico d’Orcia, and Bagno Vignoni. The countryside west of Siena is undoubtedly the least known to the general public, but no less fascinating. Without a doubt, it has remained the most authentic and least exploited area for tourism. Notable villages include Sasso Fortino, Rocca Tederighi, and Tatti, which overlook the Maremma and offer stunning sea views.
In the morning, guests will arrive at Florence or Pisa Airport, where the Slice Adventures staff will take care of their transfer to the villa in Siena, where they will stay for the entire vacation. Later, a professional mechanic will assist guests in unpacking and assembling their bikes or adjusting the position for those who have rented bikes.
Start your day cycling into the heart of Chianti, beginning in Siena and heading toward the historic Santa Margherita alla Suvera. This enchanting location, famous for its abbey and ties to Sienese nobility, is the perfect starting point to immerse yourself in the beauty of the Tuscan countryside. Surrounded by cypress trees and vineyards, it exudes authentic Tuscan tradition. Continue along the route to Pieve Asciata, a quaint church steeped in centuries of history. Its tranquil atmosphere offers moments of peace and serenity, while the surrounding landscape of olive groves and vineyards provides a sense of immersion in nature. Next, head to San Felice, an ancient village that retains its typical Tuscan architecture. Here, you’ll have the opportunity to savor the aromas of the Chianti countryside, including its famous wines and local delicacies. San Felice is also a starting point for exploring some of the region’s most renowned wineries. The final stop before returning to Siena is Castelnuovo Berardenga, a charming medieval town marking the entrance to the Sienese Chianti region. With its ancient walls and panoramic views of Tuscan hills and vineyards, it’s the perfect way to end the day.
Today’s ride takes you to the stunning Crete Senesi, one of the most striking and fascinating areas of Tuscany. Located south of Siena, the Crete Senesi are characterized by rolling clay hills, rocky formations, and white gravel roads winding through cypress trees and wheat fields. The Crete Senesi offer a true journey back in time. This area has witnessed centuries of history, reflected in its medieval villages such as Asciano, Rapolano Terme, San Giovanni d’Asso, and Castello di Cennina. Highlights include ancient churches, fortifications, mills, and Renaissance villas, all set in a tranquil atmosphere unique to Tuscany.
Rest day with a guided tour of Siena.
The first stretch of the route heads toward Monteriggioni, one of the most famous fortified villages in the region. As you cycle through rolling hills and vineyards, you’ll enjoy spectacular views of Monteriggioni’s iconic towers rising on the horizon. Once there, explore the medieval village with its imposing walls and timeless towers. From Monteriggioni, the ride continues to Abbadia Isola, a 12th-century Benedictine monastery set in a landscape that blends history and nature. This segment offers quiet roads through the countryside, perfect for a relaxing ride. Next, head to Villa Cetinale, a historic residence nestled in the Sienese hills. This stretch of the route is characterized by breathtaking landscapes of forests and vineyards. Villa Cetinale, with its centuries-old park, fountains, and gardens, represents a perfect harmony of nature and architecture.
After a short van transfer to the town of Rosia, today’s ride explores the west of Siena, the most authentic and least tourist-exploited countryside. The route includes small villages such as Belforte, Radicondoli, and Pievescola, each rich in history and surrounded by spectacular landscapes. Return: By van to the accommodation.
Transfer by van to the airport.

tour

Siena Self 7 Days Gravel

Starting at

€ 1000

taxes included

Siena Self 7 Days Gravel

Please review the bike rental prices and additional services at this link.

You can specify additional services (e.g., yoga lessons, museum visits) later. After submitting the form, our staff will contact you by email.

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