slice adventures - bike tour operator- logo

Siena Self 7 Days Road

difficulty level

Exp. level

route type

rec. perdiod

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 Airport, and the Slice Adventures staff will transfer them to the villa in Siena, where they will stay for the entire vacation. Later, a test ride will be conducted to ensure the bikes and everyone’s saddle positions are properly adjusted.
A classic route for locals, this ride features the climb to Castellina in Chianti, a charming medieval village in the heart of Chianti. Known for its famous Chianti Classico wine, Castellina offers scenic vineyards, olive groves, ancient Etruscan walls, and picturesque alleys. The village is dominated by the Rocca, a medieval fortress with a panoramic tower. After a moderate series of climbs and descents, the route leads to Radda in Chianti, another iconic town renowned for producing Chianti Classico wines. The final climb reaches Badia a Coltibuono, followed by a descent to Gaiole, home of L’Eroica, a famous vintage cycling event.
This route crosses extraordinary, highly characteristic landscapes, featuring rolling hills, challenging ascents and descents, and breathtaking views. You will visit the towns of Asciano, Buonconvento, and San Giovanni d’Asso. A must-visit stop is the Abbey of Monte Oliveto Maggiore.

 Guided tour of the city and dinner in Siena.

This is undoubtedly my favorite route. Despite the 90 km distance, it is not particularly demanding, with much of the route shaded. It runs from Siena toward the sea. From Rocca Tederighi, perched on the rocks, you can see the sea and enjoy a fantastic view. You will undoubtedly fall in love with this part of the countryside, the most unspoiled around Siena. The route begins and ends in Rosia, with a transfer organized by Slice Adventures staff.
A day full of interesting stops, each village offering unique features. Pienza, Montalcino, San Quirico, and Bagno Vignoni are each exceptional in their own way, showcasing excellent wines like Brunello, Pecorino di Pienza cheese, and extra virgin olive oil.

Breakfast at the accommodation and departure to Florence Airport.

tour

Siena Self 7 Days Road

Starting at

€ 1000

taxes included

Siena Self 7 Days Road

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.

gpx tracks

Day 1

Day 2

Day 3

Day 4

Guided tour today. GPX not available

Day 5

Day 6

Gallery