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Siena Guided 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 assist with their transfer to the villa in Siena, where they will stay 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. Dinner: In the villa with a chef.
The day begins with a ride into the heart of Chianti, starting from Siena and reaching the historic Santa Margherita alla Suvera, a fascinating location known for its abbey and ties to Sienese nobility. Surrounded by cypress trees and vineyards, it offers an authentic Tuscan atmosphere. The route continues to Pieve Asciata, a small church steeped in history. Its peaceful atmosphere and the surrounding olive groves and vineyards provide a moment of tranquility and immersion in nature. Next, the journey heads to San Felice, an ancient village that retains its typical Tuscan architecture. Here, you can savor the aromas of the Chianti countryside, including its famous wines and local products. San Felice also provides access to renowned wineries for those interested in learning the secrets of winemaking. The final village before returning to Siena is Castelnuovo Berardenga, a charming medieval town marking the entrance to the Sienese Chianti region. Its ancient walls and panoramic views make it an ideal endpoint for the day. Dinner: In the villa.
Today’s route takes you through the stunning Crete Senesi, one of the most enchanting and unique 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. This journey is a true immersion in authentic Tuscany, where nature, history, and culture blend harmoniously. The area’s medieval villages, such as Asciano, Rapolano Terme, San Giovanni d’Asso, and Castello di Cennina, tell stories of ancient times. Highlights include ancient churches, fortifications, mills, and Renaissance villas, all set in an atmosphere of calm and tranquility that only Tuscany can offer.
Guided tour of Siena and/or cooking class. Dinner: In the city center.
The first stretch leads to Monteriggioni, one of the most famous fortified villages in the region. Along the way, you’ll cycle through rolling hills and vineyards, enjoying the spectacular sight of Monteriggioni’s towers rising on the horizon. Once there, you can explore the medieval village, with its imposing walls and iconic towers that seem to stop time. From Monteriggioni, the ride continues to Abbadia Isola, an ancient Benedictine monastery from the 12th century, surrounded by serene countryside. This tranquil segment offers quiet roads ideal for a relaxing ride. Next, you’ll head toward Villa Cetinale, a historic residence nestled in the Sienese hills. This portion of the route features breathtaking landscapes of forests and vineyards. Villa Cetinale, with its centuries-old park, fountains, and gardens, represents a perfect blend of nature and architecture. Dinner: In the villa.
After a short transfer by van to the town of Rosia, the ride explores the west of Siena, the most authentic and least tourist-exploited countryside. This journey includes small villages such as Belforte, Radicondoli, and Pievescola, each rich in history and surrounded by spectacular landscapes. Return: By van to the accommodation. Dinner: In the villa.
Van transfer to the airport.

tour

Siena Guided 7 Days Gravel

Starting at

€ 2000

taxes included

Siena Guided 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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