2-Day Florence to Siena Chianti Bike Tour

Planning an escape into the rolling hills of Tuscany? If you love cycling combined with wine, food, and authentic local charm, the 2-Day Florence to Siena Chianti Bike Tour offers a well-rounded taste of one of Italy’s most picturesque regions. While I haven’t personally pedaled these roads, reviews and detailed itineraries paint a vivid picture of an experience that balances adventure, culture, and relaxation.

What really draws us in are the stunning vistas of Chianti’s vineyards, the chance to meet a world-famous butcher, and the opportunity to taste exceptional local wines and olive oils. We also appreciate that the tour is designed for small groups, making it easier to connect with guides and fellow travelers. On the flip side, the physical nature of the ride, especially if you opt out of e-bikes, might be challenging for some. It’s best suited for active travelers who enjoy a mix of scenic cycling and cultural indulgence.

This experience is ideal for those who want more than just a wine-tasting tour—it’s perfect for adventure lovers, foodies, and anyone eager to see Tuscany from the saddle of a bike. If you’re craving a taste of authentic countryside life combined with expert guides and delicious local fare, keep reading for a detailed look at what this two-day journey truly offers.

Good To Know

• Small group size ensures personalized attention and a friendly atmosphere.
• Inclusion of meals, tastings, and accommodations offers great value for a multi-day experience.
• Scenic routes through Chianti’s historic villages provide stunning views and photo opportunities.
• Guides are knowledgeable and personable, enhancing the experience with local insights.
• Optional e-bikes make the ride accessible to a broader range of fitness levels.
• Tour ends in Siena, with suggestions to stay overnight and explore the city further.

You can check if your dates are available here:

An In-Depth Look at the 2-Day Florence to Siena Bike Tour

The Overall Experience

This tour from Florence to Siena takes you through the heart of Tuscany’s celebrated Chianti region over two days. It combines active cycling with immersive cultural moments and plenty of chances to indulge in local specialties. The focus is on quality experiences—think scenic routes, top-notch wine tastings, and meeting passionate local artisans—rather than just ticking boxes.

At $811.92 per person, the cost may seem steep at first glance, but it includes bike rental, meals, wine and olive oil tastings, accommodation, and luggage transfer. This comprehensive package means fewer worries about logistics and more focus on enjoying the region. Plus, the tour is limited to eight participants, ensuring a more personal and relaxed atmosphere.

Day 1: Florence to Panzano in Chianti

The adventure begins in Florence with a warm welcome from the guides, who handle the logistics of luggage transfer—one less thing to stress about. From there, the ride kicks off with about two hours of scenic cycling, primarily on historic roads that offer sweeping views of Florence and the surrounding countryside.

We loved the way the route takes us past elegant villas and the Certosa of Florence, giving a taste of Tuscany’s architectural splendor. The ride through Bellosguardo was particularly captivating, providing plenty of photo stops and moments to appreciate the landscape. As you make your way towards San Casciano, you’ll encounter charming towns that make perfect pit stops for a quick coffee or a candid chat.

The highlight of the afternoon is the visit to a family-run vineyard. Here, you get a behind-the-scenes look at how local Chianti wines and olive oils are produced, culminating in a delicious Tuscan lunch. Guests consistently note the quality of the meal—”The flavors were exceptional, and the wine paired perfectly,” one reviewer shared. You’re encouraged to purchase bottles or oils directly from the farm, which is both convenient and authentic.

After lunch, the route takes you through Mercatale and Greve in Chianti, two towns brimming with history and character. The final ascent toward Panzano is described as the most challenging part, but it’s well worth the effort to meet Dario Cecchini, a butcher celebrated from Netflix’s Chef’s Table. Guests mention that he’s as charismatic in person as on screen, and watching him in action is a memorable highlight.

By late afternoon, you arrive at a stunning villa, where you can unwind, enjoy a peaceful evening, and reflect on the day’s adventures.

Day 2: Panzano to Siena

Day two starts with a hearty breakfast at the villa before setting off on a mostly downhill ride, which many find exhilarating. The route takes you to the town of Radda in Chianti, where a walk through its narrow streets reveals traditional buildings and panoramic views. Reviews highlight that this stop offers a great mix of history and photo opportunities.

Next, a descent takes you to Gaiole, the home of the famous L’Eroica vintage bike race. Here, the guides introduce you to local restaurateurs like Alessandra, who treats the group to a fantastic Tuscan lunch. Reviewers praise her hospitality and the authentic flavors, emphasizing that the meal is a real highlight.

The final stretch involves a scenic, gentle ride into Siena, a city renowned for its medieval architecture and vibrant culture. Since the tour ends at Siena’s train station, guests are advised to plan an extra night in the city. Siena’s car restrictions mean the van can’t go into the historic center, but guides work to get you as close as possible.

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What’s Included and What to Consider

The package includes 24-speed bikes and helmets, making it suitable for most riders. If you’re not used to cycling or worried about the physical exertion, upgrading to an e-bike for an extra $100 per person is highly recommended. The minimum age is 14, and a minimum height of 150 cm (around 4’11”) is advised for safety reasons.

Meals are thoughtfully included—two lunches, one breakfast, and one dinner—giving you fuel for the rides and a chance to savor local cuisine. The wine and olive oil tastings are highlights, with an option to purchase and ship bottles home, a handy way to bring a bit of Tuscany back with you.

Luggage transfer is seamless, and accommodation is in a comfortable villa, adding to the relaxed, boutique feel of the trip. Keep in mind that transport back to Florence is not included, so planning an overnight stay in Siena is recommended if you want to explore more.

The Real Value and Who Will Love It

At its core, this tour delivers a carefully curated taste of Tuscany’s landscapes, cuisine, and culture—crafted for active travelers who want to combine movement with authentic local experiences. The small group size fosters intimacy, allowing guides to tailor the experience and share insider tips.

The inclusion of meals, tastings, and accommodations means you won’t need to worry about extra costs, making it a solid value for a two-day adventure. Plus, the optional e-bike upgrade broadens accessibility, particularly for those who may find the physical challenge a bit daunting.

While the physical demands might be a consideration for some, especially on the climbs, the scenery, food, and wine more than compensate for the effort. The tour’s pacing, with leisurely stops and scenic routes, ensures it remains enjoyable even if you’re not a seasoned cyclist.

Final Thoughts

This 2-Day Florence to Siena Chianti Bike Tour offers a well-rounded immersion into Tuscany’s heartland. It balances active exploration with indulgent tastings and cultural encounters, all delivered by guides who know the region inside out. It’s best suited for travelers who enjoy a bit of exercise paired with authentic experiences, and who want to discover Tuscany’s villages and vineyards beyond the usual tourist trail.

If you’re looking for a memorable, intimate way to experience the region’s scenic beauty, delicious food, and world-famous wines, this tour ticks all the boxes—just be prepared for some pedaling and lively countryside air.

Frequently Asked Questions

Is this tour suitable for beginners?
If you’re comfortable riding a bicycle for a few hours and enjoy scenic routes, yes. Opting for the e-bike upgrade is highly recommended if you’re worried about the physical effort.

What is included in the price?
The tour fee covers bike rental, helmets, water bottles, professional guides, wine and olive oil tastings, two lunches, one breakfast, one dinner, one night in a villa, and luggage transfer.

Can I buy wine and olive oil from the vineyard?
Yes, you can purchase and even arrange shipping directly from the vineyard, making it easy to take a taste of Tuscany home.

What should I bring?
Bring comfortable shoes, sunglasses, sunscreen, rain gear, and your ID or passport. Dress for cycling and variable weather conditions.

How long are the cycling days?
The first day involves about two hours of riding, with some challenging climbs. The second day features mostly downhill riding, with enough scenic stops to keep it interesting.

Will I be able to explore Siena after the tour?
Yes, the tour ends near Siena’s train station, and it’s recommended to spend at least an extra night to enjoy the city’s sights and atmosphere.

Is the tour suitable for vegetarians or those with allergies?
Yes, the tour can accommodate vegetarian, vegan, and special dietary needs if notified in advance.

What if it rains?
Bring rain gear, and the guides will do their best to adapt the route if needed. The tour is generally prepared for variable weather.

Is transportation back to Florence included?
No, you’ll need to arrange your own transportation or plan to stay overnight in Siena.

In summary, this tour offers a perfect blend of active exploration, cultural richness, and culinary delights—ideal for those eager to see Tuscany from a fresh perspective, on two wheels. Whether you’re a seasoned cyclist or a curious traveler longing for authentic Italian countryside, it’s a ride worth considering.

You can check if your dates are available here: