2-Day Florence to Siena Chianti Bike Tour

Thinking about cycling through Tuscany’s rolling hills, ancient towns, and vineyards? This 2-day Florence to Siena Chianti bike tour offers a wonderful way to see some of Italy’s most iconic landscapes while enjoying local food and wine. From scenic rides on historic roads to meeting legendary butchers and tasting top-quality Chianti, this tour has a lot to offer for adventure-minded travelers.

What we love about this experience is the balance it strikes — you get active, you get relaxed, and you get a true taste of Tuscany’s soul. The guided aspect ensures you’re never lost or confused, and the small group size promises a personal touch. One thing to consider is that the tour involves some climbing and cycling; unless you upgrade to an e-bike, it might be a workout for some. Still, this trip is best suited for active travelers who want a genuine, hands-on experience of Tuscany’s countryside.

If you’re looking for a memorable couple of days that mix cycling, good company, excellent food, and stunning scenery, this tour should be high on your list. It’s perfect for those who enjoy outdoor activity but also want to indulge in the region’s culinary delights.

Key Points

Scenic Routes: Ride along historic roads offering breathtaking views of Chianti’s vineyards and medieval villages.
Authentic Experiences: Visit family-run estates, meet local artisans, and enjoy traditional Tuscan lunches.
Small Group Size: Limited to 8 participants, ensuring a personalized and relaxed atmosphere.
Cultural Highlights: Explore towns like Radda, Gaiole, and Greve in Chianti, with visits to legendary figures like Dario Cecchini.
Inclusive Options: Vegetarian, vegan, or special dietary needs can be accommodated with advance notice.
High Value: The package includes bikes, helmets, tastings, meals, accommodation, and luggage transfer, making it a comprehensive experience.

You can check availability for your dates here:

In-Depth Review of the 2-Day Florence to Siena Chianti Bike Tour

An Overview of What’s Included and Why It Matters

This tour, priced at $811.92 per person, offers more than just cycling. It’s a well-rounded experience that combines active exploration with genuine Tuscan hospitality. The price covers nearly everything — bikes with 24 speeds, helmets, water bottles, professional guides, two lunches, a breakfast, dinner, and a night’s stay at a charming villa. Plus, the luggage transfer means you don’t have to lug your bags along the routes, making the ride more enjoyable.

Not included are your transportation back to Florence, which the tour ends at Siena’s train station. If you plan to stay longer in Siena, that’s worth considering, but the logistics are straightforward. Upgrading to an e-bike for an extra $100 per person is strongly recommended if you’re concerned about the physical demands. With limited availability, it’s best to ask early—electric bikes can make those climbs much easier and less tiring.

Day 1: From Florence to Panzano

The adventure begins in Florence, where the friendly team sets the tone for a day of discovery. They handle the logistics, including luggage transfer, so you start without any worries. The first two hours are a warm-up, with a ride through Bellosguardo, an area known for sweeping views and elegant villas. Along the way, you’ll pass the Certosa of Florence, a monastery that’s been part of Tuscany’s landscape for centuries.

As the ride continues toward San Casciano, you’ll notice the countryside transforming into the classic rolling hills and vineyards that define Chianti. The highlight here is a visit to a family-run estate, where you can tour the grounds, taste their locally produced olive oil, and enjoy a hearty Tuscan lunch paired with Chianti wines. The opportunity to sample two types of olive oil and wines directly from the source is a true highlight — tasting the region’s flavors where they’re made.

Post-lunch, the route takes you through charming villages such as Mercatale and Greve in Chianti. These towns are full of character, with markets, cafes, and historic piazzas. The climb up to Panzano is the most challenging part of the day, but the reward is a visit to Dario Cecchini — possibly Italy’s most famous butcher, known from Netflix’s Chef’s Table. Meeting him, or watching him in action, brings an authentic slice of Tuscan culinary culture.

By late afternoon, you arrive at a stunning villa, your home for the night. Here, you can relax in your private room and prepare for the next day’s journey, perhaps over a glass of local wine or olive oil.

Day 2: From Panzano to Siena via Radda and Gaiole

The second day kicks off with breakfast amid the peaceful surroundings of the villa. The ride begins with a long downhill stretch, a perfect warm-up as you glide through the Tuscan landscape. You’ll pass through Radda, a quintessential hilltop village with narrow streets and panoramic views, perfect for a brief stroll before heading downhill again.

Next, the route takes you to Gaiole, home of the famous LEroica vintage bike race. Here, you’ll meet Alessandra, a local restaurant owner, who will treat you to another delicious Tuscan lunch — think fresh pasta, local wines, and friendly conversation. This stop offers a wonderful chance to connect with genuine Tuscan hospitality and learn about local traditions.

The final leg of your journey is a scenic ride into Siena. The route is gentle and winding, allowing you to soak in the landscape without feeling rushed. The tour concludes at Siena’s train station, but if you decide to stay, the city’s medieval charm — with its narrow streets, historic piazza, and stunning cathedral — is well worth a longer visit.

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What Travelers Say

Feedback from previous participants highlights the knowledgeable guides and the breathtaking scenery as key strengths. One review mentions, “We loved the way our guide explained the history of the towns while pointing out the details of the landscape,” emphasizing the educational value. Others appreciate the quality of the wine and olive oil tastings, with many describing the experience as “authentic and delicious.”

Several reviews note the physical aspect—some found the climbs challenging but manageable, especially with the option to upgrade to an e-bike. The small group size also receives praise for creating a relaxed and friendly atmosphere: “It felt like cycling with friends rather than a tour group,” one participant said.

Practical Considerations

The tour is suitable for active travelers aged 14 and up, with a minimum height of 150 cm. It’s not recommended for pregnant women or those with mobility issues. Packing comfortable shoes, sun protection, and rain gear is advised — weather can be unpredictable in Tuscany.

Since the tour ends in Siena, arranging your accommodation there is a smart move to fully enjoy the city’s beauty. Keep in mind that the tour does not include transportation back to Florence, which you’ll need to organize separately, but the Siena train station is well connected.

Final Thoughts: Is This Tour for You?

If you enjoy cycling and are curious about authentic Tuscan culture, this tour offers a balanced mix of activity, scenery, and local flavor. It’s particularly suited for those who want more than just sightseeing — you’ll get a true taste of Tuscany’s food, wine, and history. The small group format and professional guides make it a safe and intimate experience, ideal for travelers seeking a personalized adventure.

The price, reflecting a comprehensive package of bikes, meals, accommodations, and tastings, offers good value for those wanting a well-organized, multi-faceted trip. The opportunity to meet famous figures like Dario Cecchini and explore scenic villages with a knowledgeable guide makes this a memorable experience — perfect for foodies, wine lovers, and active travelers alike.

Frequently Asked Questions

What is included in the tour?
The tour includes bikes with 24 speeds, helmets, water bottles, professional guides, two lunches, breakfast, dinner, one night at a villa, and luggage transfer. Tastings of wine and olive oil are also part of the experience.

Is transportation back to Florence included?
No, the tour concludes at Siena’s train station. You’ll need to arrange your own transportation back to Florence.

Can I upgrade to an e-bike?
Yes, for an additional $100 per person, you can upgrade to an e-bike, which is recommended if you’re concerned about the physical demands of the routes.

How physically demanding is the tour?
Expect some climbs and moderate cycling, especially the final ascent to Panzano. The e-bike option helps reduce difficulty. Participants should be comfortable riding with some hills involved.

Are dietary restrictions accommodated?
Yes, vegetarians and vegans can be accommodated. Please inform the tour provider in advance if you have specific dietary needs.

What should I bring?
Comfortable shoes, sunglasses, sunscreen, rain gear, and your passport or ID are recommended. Weather can vary, so pack accordingly.

Is the tour suitable for children?
It’s designed for ages 14 and older, with a minimum height of 150 cm. It’s not suitable for very young children or those with mobility issues.

What is the group size?
Limited to 8 participants, ensuring a relaxed, personalized experience.

Final Word

This 2-day Florence to Siena Chianti bike tour offers a generous slice of Tuscany’s essence — scenic cycling, delicious local food, wine tastings, and charming towns. It’s a fantastic choice for active travelers who want to connect with the region’s culture in a hands-on way. If you’re ready for rolling hills, authentic experiences, and a memorable journey, this adventure is worth considering. Just remember to bring your enthusiasm, your sense of adventure, and perhaps a good pair of biking shoes — and enjoy every pedal stroke of this Tuscan escapade.

You can check availability for your dates here: