Siena offers a perfect backdrop for bike tours—its rolling hills, historic towns, and winding country roads make pedaling here a joy. Unlike flatter regions, Siena’s terrain invites slow, scenic rides that reveal authentic Tuscany. We’re especially fond of tours that blend stunning landscapes with cultural stops, like visiting a restored monastery or tasting fine Chianti wines. For example, the Small Group E-Bike Chianti Tour with farm lunch from Siena offers not only easy riding with electric bikes but also a chance to enjoy a local farm and winery—a delicious combination of scenery, food, and wine. It’s great for those who want to experience Tuscany intimately and comfortably.
Below, you’ll find a selection of 11 top bike tours in Siena. These range from half-day guided excursions to full-day private adventures, with options for all fitness levels and interests. Whether you’re after a relaxed cultural ride, a wine-tasting tour, or a rugged Eroica trail, this list covers what you need.
1. Small Group E-Bike Chianti Tour with farm lunch from Siena
This full-day e-bike tour takes you into the scenic Chianti Hills, with a focus on comfort and culture. The tour includes bike and helmet provision, as well as basic training—perfect for beginners or anyone wanting a relaxed ride. Over approximately 6 hours, you’ll cycle about 20 km on quiet, traffic-free roads, crossing vineyards, olive groves, and wooded areas. The highlight is a stop at a restored monastery and a local farm or winery, where you’re treated to a traditional Tuscan meal paired with generous wine tastings.
What makes this tour special is the small-group size—it keeps things intimate and allows the guide to tailor stops to your interests. The guides are praised for their helpfulness and warmth, and reviews cite the spectacular views and delicious food as unforgettable. The value is high considering the inclusions—bike, lunch, wine, and expert guidance. It’s ideal for those who want a full immersion into Chianti’s landscape with plenty of cultural stops.
Bottom line: If you prefer comfort, small-group intimacy, and a farm-to-table experience, this tour is a top pick.
2. Chianti Classico E-Bike Tour
This half-day tour showcases Chianti’s most iconic sights, including a 12th-century castle and a historic vineyard. Priced at around $309, it provides a rich, cultural experience combined with scenic riding. The tour includes a visit to the Castello di Brolio, where you can stroll the garden and private chapel, learning about its centuries-long history. You’ll then ride through Villa a Sesta and end in Castelnuovo Berardenga, a charming town full of character.
The guided commentary enhances understanding of the region’s wine heritage and landscape, making this ideal for wine lovers and history buffs. Reviews highlight the fully charged bikes and the delightful winery visit. The tour’s value is boosted by the inclusion of bottled water and wine tasting, making it a well-rounded experience.
Bottom line: Perfect if you want a shorter but comprehensive ride with excellent wine stopovers and historical insights.
3. E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles
For around $278, this 7-hour tour dives deeper into Chianti’s culinary and castle heritage. It’s a slow-paced, contemplative journey along gravel roads of the Eroica route, crossing picturesque villages and famous castles like Brolio. The highlight is a guided visit to a castle, giving a taste of long-standing Tuscan traditions. The tour also includes a Chianti wine tasting and an exploration of local food customs.
Guests who enjoy cultural storytelling and a relaxed pace find this tour particularly engaging. Reviewers mention the beautiful landscapes and the well-paced stops for photos and insights. The inclusion of castle visits and wine tasting provides excellent value for a full day’s adventure.
Bottom line: Best suited for those interested in both history and gastronomy in Tuscany, with a leisurely but immersive experience.
4. Private Ebike Tour in Chianti
This private 6-hour ride is about personalized Tuscan discovery. The tour includes bike and helmet delivery, a walk through a medieval village, and stops on white gravel roads with stunning vineyard views. Ending with a Tuscan lunch with wine, it’s perfect for couples or small groups who want an intimate experience.
Reviewers praise the flexibility of the itinerary, and guides are commended for their attention to detail. The value lies in the tailored route and private attention, making it especially suitable for travelers who prefer personalized service. The tour is ideal for those wanting a comprehensive yet relaxed day in Chianti.
Bottom line: Excellent for couples or small groups seeking a customized, private cycle experience.
5. Private E-bike Tour in Chianti from San Gimignano
Starting from San Gimignano, this 6-hour private tour offers a personalized way to explore Chianti. The guide meets you directly at your hotel or a designated spot. The route includes quiet rural roads, stops at a family farm, and a wine cellar with a tasting and traditional meal paired with local wines. You’ll also enjoy views of Siena’s skyline from the countryside.
Rated highly for personalized attention and authentic experiences, this tour is perfect if you want a more exclusive look at Tuscany. Reviewers highlight the tasty lunch and knowledgeable guide as key features. The upgraded private transportation adds extra flexibility, making it suitable for travelers with a full day to spare.
Bottom line: Ideal for those wanting a full-day, tailor-made experience combining cycling, wine, and regional scenery.
6. Saturnia and Città del Tufo in E Bike
This full-day tour covers Saturnia’s thermal springs and Pitigliano’s ancient city in the Maremma. With 6-8 hours of riding, you experience Etruscan ruins, medieval streets, and natural sulfur pools. The highlight is visiting Le Cascatelle di Saturnia, where you can relax in natural limestone pools.
Reviews are limited but positive, emphasizing the unspoiled nature of the sites and the well-organized itinerary. The tour is great for history lovers and those seeking a mix of nature and archaeology.
Bottom line: Best for travelers seeking a full-day adventure with a focus on history, natural thermal pools, and scenery.
7. By Ebike: Visit an Art Park and Wine Taste in the Classic Chianti
This 5-hour tour combines art, wine, and landscape. It features stops at hidden sculptures scattered across the hills, culminating in a wine tasting at a historic estate. Starting with storytelling, the ride covers gravel and paved roads, passing through villages and castles.
Rated just 1 review, but reviews mention beautiful scenery and informative storytelling. It’s suited for art lovers who want a relaxed ride with a splash of culture.
Bottom line: Perfect for travelers who want a shorter, arts-focused ride with wine.
8. Chianti E-Bike Tour from Siena
This half-day tour closely follows the Eroica route, offering 4-5 hours of riding through vineyards and olive groves, ending with a wine tasting at a winery. It’s a good introduction for first-timers, with mixed gravel and paved roads and breathtaking vistas.
Rated highly for the scenery and smooth ride, the tour is suitable for those with limited time but a love for Tuscan landscapes. The guided stops are well-paced, and the wine tasting is a highlight.
Bottom line: Ideal for a short, scenic ride with a focus on wine and countryside.
9. Maremma Natural Park E-bike Tour
This 6-hour guided tour explores the Maremma Natural Park, with a 30 km circuit taking in ruins, beaches, and wildlife. You’ll visit peaceful wild beaches, see ancient abbeys, and enjoy panoramic views from hilltop locations.
Reviews are positive, especially for the breathtaking scenery and easy, well-planned route. It’s perfect if you want nature and light exercise without intense riding.
Bottom line: Great for nature lovers wanting a relaxed yet scenic day in Tuscany’s coast.
10. Private E-bike Tour in Chianti from Siena
This full-day private tour offers tailored exploration, following the Via Francigena, the historic pilgrimage route. The personal guide, hotel pickup, and private lunch make this the most exclusive experience on the list. The ride includes vineyard views, medieval villages, and wine and food stops.
Guests praise the intimate atmosphere and insightful storytelling. It’s perfect for travelers seeking a luxurious, customized tour with all logistics taken care of.
Bottom line: Best for luxury travelers or those wanting a completely personalized day in Tuscany.
11. Siena: Guided Bike Tour
This 3-hour guided ride takes you through Siena’s outskirts and Monteriggioni, a medieval fortress town. With a focus on local scenery, the tour includes a light lunch with local products and wine. It’s a shorter option, perfect for those with limited time but who still want to experience Siena’s countryside.
Rated on the basis of reviews, this tour is about authenticity and simplicity, making it suited for casual cyclists and family groups.
Bottom line: Excellent for a short, relaxed introduction to Siena’s rural landscape.
How to Choose Your Siena Bike Tour
Picking the right bike tour depends on your budget, fitness level, and interests. For a full-day experience with food and wine, the Small Group E-Bike Chianti Tour offers exceptional value. If you prefer a private, personalized ride, the Private E-bike Tour in Chianti from Siena is perfect, especially if you’re traveling as a couple or small group. For those keen on history and castles, the E-Bike Tour: Explore the Chianti, its Enogastronomy and Castles is a must.
Consider your fitness level—most tours cater to casual cyclists, but the Eroica route and full-day private tours demand more stamina. Think about group size: small groups tend to enhance the experience, while private tours offer tailored insights. Booking in advance is recommended, especially during peak seasons in spring and fall.
Final Thoughts
From half-day guided rides to full-day private adventures, Siena’s bike tours cater to a wide range of travelers. If you want to soak in Tuscan scenery and sample local wines, the Chianti Classico E-Bike Tour offers excellent value. For a more personalized experience, the Private E-bike Tour in Chianti provides tailored routes and intimate moments. And if your time is limited, the Siena Guided Bike Tour is a quick, authentic way to see the countryside.
No matter your choice, these tours reveal Tuscany’s beauty on two wheels—just bring your sense of adventure and a good pair of shoes for those post-ride gelatos. Early booking is advisable, especially in high season, to secure your spot on the perfect ride. Happy cycling!
