Tuscany Bike Tours

What’s the difference between the Crossing Chianti to Siena and San Gimignano to Siena bike tours?
Both end in Siena, but the itinerary and focus differ. Crossing Chianti to Siena includes wine and olive oil tasting at an organic winery and offers a flexible distance (10–18 miles, easy to advanced), making it more wine-focused. San Gimignano to Siena instead visits two UNESCO World Heritage towns – San Gimignano and Siena – plus the medieval fortress of Monteriggioni, on a fixed easy-to-moderate route (10–13 miles), with no wine tasting included. Choose Crossing Chianti to Siena for wine tasting and flexible pacing; choose San Gimignano to Siena to see both San Gimignano’s towers and Siena’s Gothic architecture in one day. Both trips include a support van and can be adapted to each group level.

Which Tuscany bike tour is best for families with young kids?
– The Family Biking Tour is the absolute choice for Families with children, 3+.
We provide child-kid-sized bikes , rear baby seat, towing bar, E-bikes for adults as optional.
– The San Gimignano Easy Tour is most popular choice for families with kids 12+.

Do I need to be an experienced cyclist to join?
No. All our tours are designed for occasional riders as well, and E-bikes are available on every route for extra support on hills.

What’s the difference between the Crossing Chianti to Siena bike & wine tour and the Tuscany Wine Lovers tour?  Both include wine and olive oil tasting, but the focus differs. Crossing Chianti to Siena pairs one wine tasting with a full visit to Siena, and offers a flexible distance of 10 to 18 miles suited to a wide range of fitness levels, minimum age 12. Tuscany Wine Lovers is more wine-focused, with two tastings plus a wine-paired lunch at boutique organic wineries, a shorter 10 to 13 mile ride, and a minimum age of 16, but it does not visit Siena. Choose Crossing Chianti to Siena if you want wine tasting and a Siena visit in one day; choose Tuscany Wine Lovers for a deeper, unhurried wine and food experience.

Are these tours private or shared with strangers?
All our tours are small-group shared tours by default, with a maximum of 2 to 8 people (4 to 8 on Chianti Classic, Downhill to Florence, and Enchanting Florence). You’ll be joined by other travelers, never a large crowd for an immersive, still intimate experience.
The only exception is our Family Biking Tour, which is private by default. A private version of any other tour can be arranged upon request, with a custom price quotation.

What’s included in the price?
Pick-up&drop-off in Florence/ Chianti area at the most convenient meeting point, Piero, Elena Owners of the Company as your professional guides, bike and safety equipment, support van, water, and snacks. Tour-specific inclusions (tastings, lunch) are listed on each tour page.

Can non-cycling family members join?
Yes, non-riding companions can always follow along in our support van at no extra cost.

Do you offer E-bikes?
Yes, our high quality Bianchi E-bikes are available on every tour, ideal for a totally effortless trip ( highly recommended in the warm Summer days )  or less strong riders.

Is Tuscany too hilly for casual cyclists? Tuscany naturally includes rolling hills, especially in Chianti. However, our E-bike option significantly reduces the physical effort required and allows most guests to comfortably enjoy the experience.

What happens if it rains? Our support van provides flexibility in case of changing weather conditions. In severe weather situations, we always work with guests to find the best possible solution.

What time of year is best for a Tuscany bike tour?
Spring (March–May) and fall (September–November) offer the mildest weather and greenest landscapes. We run tours year-round, including warm summer and winter, with routes adapted to the season.

Do you run tours in winter or summer?
Yes. Summer tours start earlier in the day to avoid the heat; winter tours follow shorter, quieter routes. Contact us for season-specific recommendations.

What should I wear? Comfortable athletic or casual activewear is perfectly fine. Guests do not need professional cycling clothing.

How far in advance should we book?
We recommend booking at least a few weeks in advance, especially for spring, summer fall dates, our busiest season.
During peak months like Easter weeks, June, July, Fall availability can fill up very quickly.