Traveling alone?
Join a self-guided tour that has already been scheduled. We can’t run self-guided trips for one person, but we may have already booked a self-guided tour that works for you. More info


Group of three?
Tour prices are based on double room occupancy. Groups of three on self-guided trips have two options:
Option 1: Request a triple room. With a triple there is no single supplement. Option 2: Pay a single supplement (US$ 50/night) for the single room.

During the Palio (Siena's famous horserace) hotel prices triple. A surcharge of US$ 100 (per person) will apply if you stay in Siena 6/29, 6/30, 7/1, 7/2, 8/13, 8/14, 8/15, or 8/16.

• All lodging (3 and 4 star hotels)
• All breakfasts
• One lunch
• Winery visit and wine tasting
• Luggage transfer from hotel to hotel
• Private van transfer from Florence on day one
• 4 beautiful rides (15, 7, 13 and 20 miles). Extra miles available.
• Use of high-end hybrid bicycle
• Use of cell phone for emergencies

Want an easier tour?
Add a fifth night for US$ 200 (per person)

Make your trip one day longer with EASIER cycling and stay in beautiful Castellina.

Optional cooking class?
Add a cooking class for US$ 100 (per person)

Spend half a day with an Italian chef. Create a three course meal using fresh local ingredients (vegetarian classes available).

What if it rains?

Winery and Castle Admission
All of these wineries and castles can be visited on this tour. Entrance fees, if applicable, are usually less than US$ 8.

Self-Guided Siena Cycling Wineries and Castles

All of these wineries and castles can be visited on this tour. Entrance fees, if applicable, are usually less than US$ 8.

Albergaccio Machiavelli Winery, San Casciano
The Albergaccio Machiavelli winery was founded in 1693. Today they produce 300,000 bottles of wine, primarily Chianti Classico and Chianti Classico Riserva. Sangiovese, Canaiolo, and Pinot Nero grapes grow on 27 hectares of land. Nicolo’ Machiavelli wrote The Prince while living on this estate.

Il Molino di Grace Winery, Panzano
Il Molino di Grace (the ‘windmill of grace’) is the brainchild of American entrepreneur Frank Grace. This winery opened its doors in 1999 and produces critically acclaimed Tuscan wines. Cycling by you can’t miss the bold sculpture of two figures carrying grapes.

Badia a Coltibuono Winery, Radda
(Entrance not included in tour price)
The Badia a Coltibuono estate (which translates to “Abbey of the Good Harvest”) was founded by Vallombrosan monks in the 11th century and immediately became a center for wine production. Today the abbey is privately owned and still produces premium organic wines.

Brolio Castle, Radda
(Entrance not included in tour price)
The Brolio Castle dates from the 11th century and has been property of the Ricasoli family since 1141. The castle tour includes the Italian gardens, the family chapel and tomb, and the living quarters of Baron Ricasoli, a leading figure in Italian history.

Brolio Winery, Radda
(Entrance not included in tour price)
Brolio is one of Tuscany's largest wineries producing 1.5 million bottles of wine per year. See hundreds of French oak barrels in huge wine cellars. The tour concludes in a magnificent tasting room where you try three estate wines.