Florence to Siena Bike & Wine Tour Through Chianti

A Scenic Tuscany Bike & Wine Experience From Florence to Siena Through Vineyards, Medieval Villages & Rolling Hills

A full-day Tuscany bike tour designed for travelers who want to experience the real Chianti countryside at a relaxed, enjoyable pace with van support, local guidance and E-bike options available.

This is not a hardcore cycling tour.
It’s an immersive Tuscany experience designed for travelers who want to actively experience Chianti without racing through it.

• Small groups only
• Led directly by the Company owners, Piero & Elena
• Flexible ride distance (10–18 miles) – novice to expert cyclists
• Full van support throughout the day
• Real Tuscany, away from mass tourism
• Wine&EVO tasting at an organic Chianti winery
• Time to visit Siena
• Electric bikes available

Tour Details & Quick Facts

• Duration: Full Day (Pick-up at 8:45 AM, Drop-off at 5:00 PM)
• Biking Distance: 10 to 18 miles (16 to 29 km), adjustable to your fitness level
• Difficulty: Easy to Advanced (Choose your starting point)
• E-Bike available upon request
• Group Size: Small group – 2 to 8 people – Private tour  – larger groups can be accommodated upon request.
• Route : Castellina in Chianti – Lornano – Siena (opt.departure from San Donato in Poggio longer distance – Active Riders)
• Minimum Age: 12 years old
• Non-riding travel companions are always welcome to join the experience! Feel free to contact us for more details.

What is Included

• Round-trip air-conditioned van transfer from a designated meeting point in Florence. Please note that if you are staying outside Florence, we will be happy to arrange a customized countryside meeting point for your convenience.
• Expert guidance by owners Piero & Elena (Licensed Tour Operator since 2013)
• Full guidance and van support
• High-quality 27-speed light-frame fitness bicycle, helmet, and water bottle
• Optional : High-end E-bikes upgrade are available upon request for an easier ride.
• Full wine tour and tasting (Chianti Classico, extra virgin olive oil, and balsamic vinegar) at a local organic winery (tasting fees included)
• Snacks and fresh fruit during the bike ride
• City maps and insider recommendations for lunch in Siena

Tour Highlights

• Explore San Donato in Poggio, one of Italy’s most beautiful medieval villages.
• Walk through the 15th-century arched passages of Castellina in Chianti.
• Cycle safely on scenic roads surrounded by vineyards, olive groves, and cypress trees.
• Discover the history of the “Black Rooster” symbol at the historic Fonterutoli Castle.
• Stop at an historical winery along the way for wine education, tasting best selection of organic Chianti wines, balsamic vinegar, EVO.
• Enjoy free time to sightsee and have lunch in Siena’s historic center ( approx 2-hour stop ).

Ready To Experience Tuscany By Bike?

Your Itinerary Step-by-Step

1. Morning Transfer & San Donato in Poggio After an 8:45 AM pick-up in Florence, we drive comfortably into the Chianti Classico region. Our first stop is the picture-perfect village of San Donato in Poggio, where you can enjoy a morning cappuccino and take your first photos of Tuscany.
2. Castellina in Chianti & Bike Fitting We then head to Castellina in Chianti to explore its medieval square and historic arched passages. Here, we fit you with your bicycle and safety equipment.
3. The Chianti Scenic Ride Start your pedaling adventure on gentle, low-traffic roads. We will stop at gorgeous viewpoints for souvenir photos and pass by the amazing Fonterutoli Castle, an antique hamlet owned by a noble family since 1435, where you will learn about the iconic “Black Rooster” symbol of Chianti.
4. Organic Wine & Olive Oil Tasting Our ride takes us past beautiful vineyards to the historical residence of Lornano, an authentic organic winery. We will stop here for a guided tour and a rich tasting of Chianti Classico wine, extra virgin olive oil, and balsamic vinegar.
5. Siena Exploration & Return to Florence To avoid city traffic, we end the biking portion with one last panoramic view before driving you to the medieval walls of Siena. You will have free time to explore the Gothic Cathedral, Piazza del Campo, and enjoy a local lunch or gelato. After your visit, our van will drive you safely back to Florence by 5:00 PM.

Join our Florence to Siena bike & wine tour through Chianti and discover Tuscany at a slower, more authentic pace.

WHAT MAKES BIKE FLORENCE & TUSCANY DIFFERENT

Since 2013, we have focused on combining:

• genuine local guidance
• scenic secondary roads
• flexible pacing
• authentic Tuscan atmosphere
• small groups
• personal attention

Rather than creating high-volume tourist experiences, our goal is to help guests experience Tuscany in a more personal, relaxed and memorable way.

FAQ (Frequently asked Questions)

• Can beginners join this Tuscany bike tour? Yes. Many guests are recreational riders rather than experienced cyclists. Different distances to travel, E-bikes and van support make the tour accessible to a broad range of fitness levels, from novice to expert.
• Is this Tuscany bike tour difficult? No. The tour is designed for different fitness levels and includes multiple ride options ranging from about 10 to 18 miles.The support van is available throughout the day. Electric bikes are also available.
• 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.
• Is van support included? Yes. Our support van remains available throughout the tour for assistance, breaks or weather-related support.
• Are E-bikes available? Yes. E-bikes are available and highly recommended for guests looking for a more relaxed 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.
• Is lunch included in the price? Lunch is not included, allowing you the freedom to choose your preferred meal during your free time in Siena . We will provide a map and our best local restaurant recommendations.
• What should I wear? Comfortable athletic or casual activewear is perfectly fine. Guests do not need professional cycling clothing.