Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124
Physical Address
304 North Cardinal St.
Dorchester Center, MA 02124

Discover Chianti’s stunning landscapes, historic castles, and exceptional wines on this 7-hour e-bike tour starting in Siena, including tastings and a Tuscan lunch.

This e-bike tour in Siena offers a detailed exploration of Chianti’s scenic hills, famous castles, and wine traditions. Priced at $277.82 per person, it lasts approximately 7 hours and 15 minutes and is designed for those who enjoy slow, contemplative journeys through Italy’s celebrated wine country. Guided by a certified expert, the tour combines biking, history, and culinary delights, making it ideal for visitors with moderate physical fitness who appreciate authentic Tuscan culture.
What sets this experience apart is its focus on Chianti Classico wine, with a tasting included at the renowned Castello di Brolio, and the opportunity to visit historic castles and picturesque villages. The tour also emphasizes local gastronomy, with a lunch at a family-owned restaurant in San Gusmé, allowing guests to enjoy traditional Tuscan dishes in a tranquil setting. The inclusion of pickup and group discounts further enhances convenience and value.
While no lunch is included in the base price, the overall experience offers a full day of culture combined with active cycling in beautiful landscapes. The small group setting ensures personalized attention, and the tour is suitable for those who enjoy moderate physical activity and history, wine, and food.

Enjoy cycling? We've looked into these other two-wheeled adventures in Siena

This 7-hour and 15-minute tour begins at Via Mentana, 38, Siena, and ends back at the same location. The pickup service simplifies logistics, and the day is paced to include several stops for sightseeing, tasting, and relaxation. The tour is designed for those who enjoy active exploration combined with cultural stops.
The journey kicks off with a ride from Siena to the village of Geggiano, where a short pause allows for storytelling and photo opportunities. From there, the route follows Chianti’s famous white gravel roads, including stretches known for the Eroica cycling race. The landscape features cypress-lined roads and castles, creating a classic Tuscan backdrop.
Passing by Vallepicciola Winery, the ride transitions into hilly terrain with spectacular views of Siena’s skyline and the surrounding vineyards. The white gravel roads and castle vistas enhance the visual appeal of this bike route, which balances riding moments with scenic stops for sightseeing and storytelling.

At Villa di Geggiano, the tour makes a brief stop outside the castle, where guides highlight the Bianchi Bandinelli family’s influence and the production of Chianti Classico. Guests enjoy a photo opportunity with a sweeping view of Siena in the background. This stop emphasizes local history and the importance of wine production in the area.
The visit underscores Chianti’s long-standing tradition of winemaking, providing context for the tastings to come. The villa’s exterior offers a glimpse into Tuscan aristocratic life, making it an enriching moment in the journey.

The route continues through hilly landscapes, passing castles and vineyards, with multiple stops for pictures and storytelling. The ride progresses toward Monti in Chianti, a small hamlet where local caffe gives riders a chance to stretch, refresh, and sample Sienese biscuits and pastry. This break allows for rest and socializing before heading toward the Cacciano Castle.
The climb toward the Brolio Castle involves passing by several castles, with stunning landscape views en route. The 30-minute ride from Monti in Chianti offers a mix of riding and sightseeing, setting the stage for the castle visit.
While in Siena, here are other experiences we've covered

The highlight of the tour is the visit to Castello di Brolio, where a local guide leads a comprehensive tour of the castle’s interiors and grounds. Guests learn about the historical conflicts between Siena and Florence and the Ricasoli family’s role. The guide also explains the castle’s architecture and history, providing rich context.
Inside the castle, visitors explore installations and historical artifacts, gaining insight into local history. The tour concludes with a visit to the wine cellar, where a tasting of Chianti Classico wines is included, offering a chance to savor one of Italy’s most celebrated wines.

After touring the castle and cellar, guests visit Barone Ricasoli, where they sample one glass of Chianti Classico or other wines from their selection. The wine tasting lasts about 30 minutes and provides an opportunity to sample different varieties. Additional glasses can be purchased if desired.
This part of the experience highlights the quality and diversity of Chianti wines and offers expert insights from the staff. It’s a relaxed moment to appreciate local winemaking craftsmanship.

Following the wine tasting, the group makes a quick stop at Agribar Brolio, an old-style bar known for its atmosphere and history. Here, guests enjoy water, snacks, and a chance to rest before resuming the ride. This 15-minute pause helps reset the pace and prepares everyone for the later stages of the day.
The tour then proceeds to Borgo di San Gusmé, where a guided visit and wine tasting at Brolio/Ricasoli set the stage for the lunch break. The restaurant is located in this charming hamlet, known for its monuments and local culture. Guests spend around 1 hour and 30 minutes enjoying Tuscan specialties in a tranquil setting.
The lunch experience offers a chance to relax, explore the village, and savor typical Tuscan dishes, making this a genuine culinary highlight of the tour.
The final part of the journey involves returning to Siena on gravel and local roads, with several short stops for storytelling and photo opportunities. The cycling pace is leisurely, allowing ample time to absorb the scenery and appreciate the landscape. The return route emphasizes the rural beauty of Chianti and the enduring charm of its villages.
The trip concludes back at the starting point, with a total riding time of around 1 hour and 30 minutes, ensuring a satisfying yet manageable activity for most moderate fitness levels.
This private experience includes a guided castle tour, wine tasting at Ricasoli, and the use of high-quality bicycles. The certified guide from the National MTB Academy offers in-depth local knowledge. Emergency mechanical assistance is available, ensuring peace of mind during the ride.
Not included are the lunch at the restaurant, bottled water, and other food or beverages consumed during cycling. The meeting point is accessible and near public transportation, making it easy to join.
This e-bike adventure appeals to active travelers who want to explore Chianti’s landscapes at a relaxed pace. It’s perfect for those who enjoy historical castles, wine tastings, and Tuscan cuisine. The small group format enhances the experience with personalized insights and flexibility.
While not suited for low fitness levels, the tour is manageable for anyone comfortable with moderate cycling. The emphasis on cultural and culinary highlights makes it ideal for enthusiasts of food, wine, and history.
This e-bike tour in Siena offers a well-rounded immersion into Chianti’s landscape, castles, and wines. With guided visits, wine tastings, and a Tuscan lunch, it provides a full day of discovery in some of Italy’s most beautiful settings. The stunning views, historic sites, and delicious food make it a rewarding experience for those seeking cultural depth and active exploration.
The balance of cycling, sightseeing, and tasting ensures an engaging and enjoyable day, especially for moderate fitness enthusiasts who appreciate authentic local flavors. While the lunch is not included in the base price, the overall value remains high considering the guided tours, tastings, and scenic routes.
“I just completed an unforgettable experience with an ebike tour in Chianti and I can't help but recommend it to anyone looking for a unique adventu…”
Is the tour suitable for children or families?
This tour is designed for those with moderate physical fitness and may not be ideal for very young children or those requiring assistance.
Are the bicycles provided suitable for all riders?
Yes, the use of bicycles is included, and the tour features professional mechanical assistance in case of breakdowns.
Can I customize the wine tasting options?
Guests receive one glass of Chianti Classico included in the tasting, with additional options available for purchase.
Is lunch included in the tour price?
No, lunch at a family-owned restaurant is not included but is part of the overall experience.
What should I bring for this tour?
Bring comfortable clothing, moderate fitness level, and sun protection. Bottled water is not provided but can be purchased or brought along.
How far in advance should I book?
The tour is frequently booked about 70 days in advance, so planning ahead is recommended.
What weather conditions are acceptable?
The experience requires good weather; in case of rain or poor conditions, the tour may be canceled or rescheduled.
Is transportation provided to the starting point?
Pickup is offered at Siena, simplifying arrival, but private transportation is not included.