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Experience Tuscany on a 2-day guided e-bike tour from Florence to Siena, exploring Chianti's scenic vineyards, medieval towns, and enjoying wine and Tuscan cuisine.


This 2-day e-bike tour from Florence to Siena offers a deep dive into the heart of Chianti’s rolling hills, combining scenic cycling, cultural stops, and authentic Tuscan flavors. The tour includes all necessary arrangements, making it ideal for those who want a hassle-free experience of Tuscany’s most famous landscapes and towns. The experience is designed for active travelers aged 14 and up, with a minimum height requirement of 150 cm.
A key feature is the overnight stay in a picturesque villa surrounded by vineyards, giving participants a chance to relax and unwind in a true Tuscan setting. The fully-inclusive package covers visits to boutique wineries, wine tastings, traditional Tuscan lunches, and encounters with local personalities such as Dario Cecchini, the renowned butcher of Panzano. This tour is perfect for those seeking a combination of outdoor activity, cultural exploration, and delicious food and drink.
One consideration: the tour ends in Siena, with limited options for the return trip, so an overnight stay in Siena is recommended to fully enjoy the city’s beauty.
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The tour begins at “We Like Tuscany”, located at the coordinates 43.76612854003906, 11.243185043334961, with a simple call to ring the bell on the left of the grey gate. The initial meeting point offers the convenience of luggage transfer, so travelers can start cycling without baggage concerns.
With small group sizes capped at 8 participants, the experience promises personalized guidance and a more intimate atmosphere. The guides communicate in English and Italian, offering insights into the local culture and scenery along the way.

The first day kicks off in Florence, with a scenic two-hour ride that takes cyclists along historic roads, passing elegant villas and offering spectacular views of the city and the famous Certosa of Firenze monastery.
The route heads into the San Casciano area, a charming town at the heart of Chianti. Here, a visit to a family-owned wine estate provides a chance to tour the property and taste Chianti wines and locally produced olive oil. A traditional Tuscan lunch follows at the estate, offering a genuine taste of regional cuisine paired with more wine.
Post-lunch, the ride continues through the medieval villages of Mercatale and Greve in Chianti, each steeped in history and charm. The final challenge for the day is a climb up to Panzano in Chianti, where travelers meet the legendary butcher Dario Cecchini—a highlight for those interested in Tuscan culinary traditions.
By late afternoon, the group reaches a stunning villa, perfect for relaxing at the pool or enjoying the peaceful vineyard surroundings before a delicious dinner.
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The second day begins with breakfast at the villa before embarking on a long downhill ride that takes cyclists through Tuscany’s lush scenery. The first stop is Radda in Chianti, a picturesque medieval town known for its scenic views and historic streets.
After exploring Radda, the tour continues with another descent into Gaiole in Chianti, famed as the home of the Le Ruca vintage bike race. Here, participants enjoy a traditional Tuscan lunch with wine, savoring regional flavors before the final stretch.
The last ride takes in more scenic views, leading to the city of Siena, where the tour typically concludes at the train station. If travelers choose to stay in Siena, the guide will assist with drop-off near the city center, though the tour does not include the ride back to Florence.

The stops in Radda, Gaiole, and Greve each offer a glimpse into Tuscany’s rich history and vibrant food culture. Radda’s quaint streets and panoramic views provide a perfect photo opportunity, while Gaiole’s association with Le Ruca connects cycling culture with local tradition.
The visit to Dario Cecchini in Panzano is a unique chance to see a renowned butcher in action, a true highlight for food lovers. The villa stay at the end of Day 1 provides a serene setting to unwind, with options for swimming and relaxing after a day of active exploration.

The tour starts at “We Like Tuscany” in Florence, with luggage transfer included, ensuring a smooth beginning. The group size remains small, fostering a personalized experience with attentive guides.
Participants are advised to bring passport or ID, comfortable shoes, sunglasses, sunscreen, and rain gear just in case. The tour is designed for those aged 14 and above, with a minimum height of 150 cm.
The end point is Siena, where luggage can be dropped at the San Domenico church or the train station. Since Siena has a restricted traffic zone, the van cannot enter the city center, so plan accordingly for your onward journey.
The journey offers a mix of picturesque landscapes, from historic roads to vineyard-covered hills. The ride through medieval towns like Mercatale, Greve, Radda, and Gaiole enriches the experience, adding layers of history and local charm.
The downhill segments are especially enjoyable, providing relief after climbs and allowing for scenic leisurely rides. The presence of boutique wineries ensures tasting authentic Chianti wines, complemented by delicious Tuscan lunches and olive oils.
The chance to meet Dario Cecchini, the legendary butcher from Netflix’s “Chef’s Table,” is a real highlight. His in-action demonstrations showcase Tuscan culinary craft, adding a memorable highlight to the trip. This encounter offers insight into local food traditions that go beyond just tasting.
The overnight stay occurs at a charming villa surrounded by vineyards, offering a peaceful retreat after a full day of cycling. Guests can relax at the pool, enjoy the scenic views, or simply unwind before dinner, making this a well-rounded experience blending activity with comfort.
The tour concludes in Siena, leaving ample opportunity to explore the city’s stunning architecture and historic sites. The drop-off is near the city center, facilitating easy access to local accommodations or further sightseeing.
A recommendation is to plan an overnight stay in Siena to enjoy its vibrant streets, famous square, and incredible cuisine. Since the tour ends there, travelers get to explore Siena’s charm at their own pace.
For those interested in further Tuscan adventures, similar experiences include wine tastings, pasta cooking classes, and day trips to Pisa or San Gimignano. Links provided in the source guide offer a variety of options for extending the Tuscan journey.
This 2-day guided tour offers a blend of active cycling, culinary delights, and cultural stops. The inclusion of boutique winery visits, meeting a famous butcher, and staying in a picturesque villa make it stand out.
The small group size ensures personalized attention, while the scenic routes and historic towns promise a memorable exploration of Tuscany’s iconic landscapes. The all-inclusive nature simplifies planning, making this an appealing choice for active travelers who want to experience Tuscany authentically.
Is this tour suitable for beginners?
Yes, the tour is designed for active individuals aged 14 and above with a minimum height of 150 cm. The use of e-bikes makes climbing easier, and the guides will accommodate different riding levels.
What should I bring for the tour?
Participants should bring passport or ID, comfortable shoes, sunglasses, sunscreen, and rain gear. It’s also advisable to carry a small backpack for personal items.
Can I stay longer in Siena after the tour?
Yes, since the tour ends in Siena, you are encouraged to stay overnight to explore more of the city’s sights and enjoy its vibrant atmosphere.
Are dietary restrictions accommodated?
The tour can accommodate vegetarians and vegans, and requests related to food allergies or specific dietary needs should be communicated in advance.
What happens if I need to cancel?
You can cancel up to 24 hours before the tour for a full refund. The booking process also allows you to reserve now and pay later with flexible options.