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Reserve This Tour Get Detailed Itinerary

Price

US$ 900 per person
(Single Supplement)

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.

Save US$ 100 per person
Use our bike bags (panniers) instead of the luggage transfer
» more info

Optional Charges
» Cooking Class (US$ 75 per person)

Dates

Any date from March 1 to October 31
5 Days, 4 Nights
Route Rating
Moderate: 10-20 miles per day cycling over hilly terrain.

Meet / Finish
Florence / Volterra
Highlights
  • Winery visit with guided wine and oil tasting
  • Towers of San Gimignano
  • Roman amphitheater of Volterra
  • Beautiful Tuscan scenery and peaceful country roads
  • The town of Volterra

What's Included
  • All lodging (3-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 (19, 9, 13 and 21 miles). Extra miles available.
  • Use of high-end hybrid bicycle
  • Use of cell phone for emergencies

Cancellations: Terms and Conditions

» Tour Summary
» Map and Distances
» Hotels
» Photos
» Bicycles


Wineries and Castles
Optional cooking class?
Add a cooking class for US$ 100 (per person)
Chianti cooking class
Spend half a day with an Italian family at their country house. Learn to make traditional Tuscan cuisine with produce from the family garden. (vegetarian classes available).

What if it rains?

On self-guided bike tours there is no van support. However, we do move your luggage from hotel to hotel. In the event of rain you can catch a ride with us when we move your bags. We provide our guests with a cell phone. You can call in the morning and make arrangements for a lift.


Why Self-Guided?
Explore Tuscany at your own pace. We provide detailed route notes, luggage transfers, great accommodations, restaurant suggestions, and sightseeing notes. You choose the dates we take care of the details.

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 San Gimignano 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.
Palazzo Pretorio Castle, Certaldo Alto
(Entrance not included in tour price)
Palazzo Pretorio was originally the castle of the Conti Alberti family. Its facade is decorated with coats of arms. Inside is a museum with frescoes and Etruscan and Roman antiquities. The castle is the highest structure in Certaldo and offers amazing views of the surrounding countryside.
Tenuta Torciano Winery, San Gimignano
The Giachi family has been making wine for three centuries. Today Pierluigi Giachi continues the family tradition producing Tuscan reds and the white Vernaccia di San Gimignano. The winery offers guided tastings, but not winery tours.
Castelvecchio Castle, San Gimignano
An abandoned castle reachable only by a 30-minute walk. The fortress was abandoned after the plague of the 15th century. Today you can explore the remains of a defensive tower, houses, shops and a Romanesque church. Castelvecchio was one of 20 castles which formed a defensive ring around San Gimignano.