Randonnee Tours - Tuscany cycling 8 days: tuscany
Enjoy la dolce vita! Tuscany is the classic Italian destination, and this adventure offers you famous sights and unusual discoveries. Travel at your own pace and take time to experience the best of Tuscan living.

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Active Adventure

Enjoy la dolce vita! Tuscany is the classic Italian destination, and this adventure offers you famous sights and unusual discoveries. Travel at your own pace and take time to experience the best of Tuscan living. Explore winding walkways in Sienna and ride through hilltop villages in the heart of Chianti, San Gigminano, Castellina, Monterrigioni, Asciano, Pienza,and Montepulciano.

Typical Day


Day 1
Arrival in Siena. Siena is one of the most enchanting cities in Italy. Take some time to visit the medieval centre with majestic buildings, such as the palazzo Comunal on Il campo and a profusion of churches and small museums rich in artworks.

Day 2
Starting from Siena, cycle north through fields and vineyards, stopping in San Sano at a favorite restaurant for lunch. Afterwards, you can visit Radda on your way to Castellina.

Day 3
Today choose between a route through the surrounding countryside with a visit to Castle Meleto or a route to San Gigminano, with its medieval towers evoking times past. Back in Castellina, opportunities are many for wine tasting at one of the enotecas in town. Your hotel in Castellina, formerly a palace is now a charming hotel with swimming pool and stunning common rooms.

Day 4
Sovicille: Your route today takes you to Monterrigioni; with its perfectly preserved walls and cobbled streets you will find the charm immediate. Your hotel, located in the country-side with pool and surrounded by an extensive park, may tempt you to relax. For those interested in cooking lessons prior to dinner, please call the office for details.

Day 5
Asciano, this will be a favorite day of riding as you pedal through rolling countryside lined with cypress trees. Asciano is full of museums and monuments, and is also a perfect base to reach the Abbey of Monte Oliveto Maggiore, where monks still produce wine, honey, olive oil and a cure-all herb liquor. Art lovers will not want to miss the frescoes painted by Sodoma and Signorelli that have been preserved here since the 15th century. Your 3-star hotel in Asciano is brand new with swimming pool and gardens.

Day 6
Pienza, We save the most spectacular riding for last as you visit the tiny villages of Petroio and Castelmuzio on your way to Pienza, full of Renaissance monuments; your hotel here is quietly situated 150 meters from the central plaza and has large comfortable rooms and a casualness that you will enjoy (and a brand new pool in 2007).

Day 7
On your final day or riding, you’ll ride to Montepulciano, riding through a ‘photographers’s paradise’. Montepulciano is the biggest and highest of Tuscany’s hill towns at 655 meters with medieval alleyways and lots of Renaissance palaces and churches.The surrounding countryside produces a wine called Vino Nobile di Montepulciano and has been doing so since the 8th century.

Day 8
Departure day. Be sure to spend a final few moments enjoying the delights of Tuscany before you catch your train to your next destination.

Age range, type of group

Level of Activity
Moderate/Challenging 20-40+ miles daily, 1 day gently rolling, 3 days are moderately rolling, 2 days are hilly.

Sleeping and meals

You’ll stay at lovely 3-star hotels: Il Giardino in Siena, has a swimming pool and is located just outside the historical walls of the city. Palazzo Squarcialupi in Castellina (2 nights) A former palace, now one of the top hotels in Chianti. Villa Cennina, Sovicille (1 night) A country hotel, in the hills south of Siena, surrounded by extensive park with large pool and garden. Hotel La Pace, Asciano (1 night) Built in 2002, this 3-star hotel has an excellent family restaurant. Hotel San Gregorio, Pienza (2 nights) We stay in large suites in this hotel, located steps to the historical district of Pienza.
Luxe upgrade available in Pienza (Hotel Il Chiostro) and Sienna (hotel Santa Caterina).

Other Information

Price Includes
-7 nights’ accommodation in country inns and 3 stars hotels
-All breakfasts + 2 dinners
-Use of a top quality 21-speed hybrid bike, complete with pump, patch kit, water bottles. We recommend you to bring your own helmets for safety and hygiene reasons.
-Detailed instruction and maps
-Luggage transfer

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Randonnee Tours - Tuscany cycling 8 days

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Listing # RA-1128246