Crossing Chianti to Siena
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.
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)
- Time to visit Siena : two hour stop to explore the village highlights & lunch on your on
- Minimum Age: 12 years old
- Non-riding travel companions are always welcome to join the experience! Feel free to contact us for more details.
PRICE
€ 160 per person
( min. 2 participants required )
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
- Morning Transfer & San Donato in Poggio After an 8:45 AM pick-up in Florence (please notice that we are happy to organize your pick-up&drop-off at the most convenient free parking lot in the countryside if you are staying outside of 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.
- 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.
- 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.
- 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.
- 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.
PERFECT FOR
If this sounds like your kind of Tuscany…
Travelers who want the classic Tuscany experience by bike: vineyards, quiet country roads, Chianti wine, medieval landscapes and time to explore Siena. The route can be adapted to different fitness levels, with van support throughout the day, making it a particularly good choice for recreational riders who want to ride without feeling pressured
CONSIDER THIS INSTEAD
If your priority is…
- You only have one day in Florence and don’t want to leave the city. Enchanting Florence covers the artisan quarters, the Arno and Piazzale Michelangelo in five hours, no transfer. (12+)
- Wine is the whole reason you are coming to Tuscany. Tuscany Wine Lovers includes two tastings at boutique producers and a full wine-paired lunch. (16+)
- You want medieval hill-top towns rather than vineyards. San Gimignano to Siena links three of them — San Gimignano, Monteriggioni and Siena — in a single day. (12+)
- You are travelling with children under 12, or want a private day built around your family. The Family Biking Tour is private by default, with kids’ bikes, towing bars and baby seats. (3+)
- You are a trained cyclist who wants real climbing. Chianti Classic takes on Radda, Brolio and Gaiole — 25 to 32 km of genuine Chianti hills. (14+)
- You only have half a day. Downhill to Florence starts at Monte Senario and drops you back in the city by early afternoon. (12+)
WHAT MAKES BIKE FLORENCE & TUSCANY DIFFERENT
Bike Florence & Tuscany is a founder-led Tuscany Biking Company specializing in authentic small-group experiences departing directly from Florence and surroundings.
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
- 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.
WHAT OUR GUESTS SAY
EXPLORE TUSCANY WITH OUR EXCLUSIVE TUSCANY BIKE TOURS
