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 Siena and ride through hilltop villages in the heart of Chianti, San Gigminano, Castellina, Monterrigioni, Asciano, Pienza, Montepulciano, and Montalcino.
Siena, Province of Siena, Italy
Siena, Province of Siena, Italy
Asciano, Province of Siena, Italy
Pienza, Province of Siena, Italy
Montepulciano, Province of Siena, Italy
Montalcino, Province of Siena, Italy
What’s Included in the Cost of Your Trip?
INCLUDED IN REGULAR TRIP
9 nights hotels
All breakfasts and 2 dinners
Details with detailed pre-trip information
Detailed route instructions and maps
Personal meet & greet with our local Area Manager
Area manager available on call throughout the tour
Access to Loyalty Program and other exclusive benefits
We require that you bring your own helmet for safety and hygiene reasons
We recommend to start this tour on a Thursday to see the market in Sinalunga held every Tuesday.
ARRIVE / DEPART
Classic Accommodation: US $2,950
Single Supplement: US $740
Luxe Accommodation: US $3,450
Single Supplement: US $865
Hybrid or Racing Bikes: US$400
E-bikes are generally available but are on an ‘on request basis ‘ and will be confirmed on receipt of your booking registration. E-bikes provided are the best rentals available in the region. Our regular fleet of hybrid and race bikes are fun to ride and light and fast, but if having an e-bike will make your trip, we’ll do our best to provide. E-bike rentals are non-refundable.
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.
Castellina in Chianti
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.
Ride Distance: 46 km, elevation gain 690 m.*
Castellina in Chianti
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.
Ride Distance: 52 km, elevation gain 699 m or 62 km, gain 868 m.*
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.
Ride Distance: 64 km, elevation gain 576 m or53 km, gain 693 m.*
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.
Ride Distance: 43 km, elevation gain 541 m or 23 km, gain 255 m.*
Following quite rolling roads south, you’ll 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).
Ride Distance: 30 km, elevation gain 495 m.*
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. We’ll recommend local enotecas where you can taste.
Ride Distance: 37 km, elevation gain 485 m or 45 km, gain 651 m.*
Ride through a classic Tuscan tableau of cypress trees, pines and olive groves to the ancient village of Bagno Vignoni; see a Roman bath favored by members of the Medici family. Continue to Montalcino, a picturesque town famous for Brunello wines and medieval architecture.
Ride Distance: 45 km, elevation gain 750 m.*
On this day loop from Montalcino, you will cycle to Buonconvento, a picturesque 14th Century medieval village and to the Bibbiano fortress that overlooks the Ombrone Valley.
Ride Distance: 48 km, elevation gain 532 m or 24 km, gain 182 m.*
Departure day. Be sure to spend a final few moments enjoying the delights of Tuscany before you catch your train to your next destination.
*Distance and elevation gains may vary depending on hotels chosen for specific departure
This charming 3-star hotel is a favourite in Sienna. Boasting a beautiful view over the countryside and a 10 minute walk to the historical center, its location is also ideal for cycling out of town on Day 2. The rooms feature high ceilings and the breakfast is superb.
This charming hotel has comfortable rooms, and a lovely swimming pool. Located close enough to walk (150 m) to restaurants in Castellina-in-Chianti.
Located among the hills of the Crete Senesi and the Val di Merse, this hotel boasts outstanding views in every direction, a large swimming pool and a tranquil setting. There is a restaurant catering to guests on site.
This property is our newest discovery; this family-owned 17th century property is surrounded by vineyards (the family makes outstanding wines), olive trees and organic gardens. There is a heated swimming pool to enjoy on the property. There isn’t a restaurant on the property but there are two good options, one right next door and another 900m distant.
This 3-star hotel has very large rooms and swimming pool and is conveniently located steps to the historical district of Pienza. Breakfast is served in an adjoining restaurant.
The Vecchia Oliviera Hotel is a fascinating ancient olive-oil mill that has been carefully renovated. Both its location and warm service make it a relaxing place to stay. Swimming pool.
This 18th century villa has been converted into a cozy hotel. Guest rooms overlook the valley. It is steps away from the medieval city gates with lots of restaurants to choose from.
This palazzo boasts a superb location, right in the historic center of village, largue sumptuous lounges and bar, and a large outdoor swimming pool.
This 4-Star Tuscan villa boasts panoramic views over vineyards, with a pleasant swimming pool in a very quiet setting. There is a small bar serving light food; good restaurants can be reached 1 km distant.
This eighteen-century property is one of the most magnificent 4-star hotels in Tuscany. There is a large swimming pool, a hydro-massage bath tub, and tennis-courts, all surrounded by an amazing landscape and a good restaurant on site.
Formerly a Franciscan convent, this 4-star charming hotel boasts comfortable rooms, outdoor swimming pool and a fine restaurant with terrace overlooking the stunning Val d'Orcia valley.
This charming hotel is Montalcino's best - family run, on a quiet street in the historic centre. "...the best part is the view of the cliff-clinging houses of Montalcino to your left and the rumpled patchwork of green valleys stretching out below." - Lonley Planet