2 day(s)
English
Included
2-day immersive Chianti Classico bike tour from Florence to Siena
Ride scenic backroads through medieval towns, vineyards, and rolling hills
Visits to family-run wineries and farms with wine and olive oil tastings
Meet world-renowned butcher Dario Cecchini in Panzano
€ 679
This activity is managed by our trusted partner FareHarbor.
Additional taxes and fees may apply — total shown at checkout.
Select your preferred date and time from the calendar above.
Free cancellation and unlimited rescheduling leads to total flexibility while you plan your travels
Lowest Price Guarantee — no other provider offers this tour for less
Experience the heart of Tuscany on this immersive 2-day Chianti Classico bike tour, connecting with nature, local life, and authentic Tuscan flavors.
Starting from Florence, ride through scenic backroads from San Casciano to Gaiole in Chianti, avoiding highways and discovering medieval towns, panoramic views, and hidden corners of the countryside. Enjoy stops at family-run wineries and farms to taste Chianti wines, olive oils, and traditional Tuscan dishes. Electric bikes are available for a more relaxed ride.
Day 1 begins with a morning ride through Bellosguardo, taking in villas, ancient roads, and the Certosa of Florence monastery. Continue to San Casciano, visit a wine estate for a guided tour and lunch, and taste multiple wines and olive oils. The afternoon ride passes through Mercatale and Greve in Chianti, ending in the hilltop town of Panzano, where you’ll meet the world-renowned butcher Dario Cecchini, followed by relaxation at a countryside villa with dinner.
Day 2 starts with a downhill ride to Radda in Chianti, then onward to Gaiole for a traditional Tuscan lunch in the town square. The journey continues along scenic semi-downhill routes through Pianella, finishing in Siena, offering an unforgettable blend of cycling, culture, gastronomy, and Tuscan landscapes.
Expert bilingual guide
High-quality bikes or electric bikes
Helmets, water, and basic bike support
Visits and tastings at wineries and farms
Two lunches and one dinner
Luggage transfer between accommodations
Personal expenses
Gratuities (optional)
Drinks or food not specified in inclusions
Passport or ID card
Comfortable shoes
Sunglasses
Sunscreen
Rain gear
Moderate to high cycling fitness required
Comfortable clothing and shoes recommended
Bring a fully charged phone and power bank for navigation
Tour runs in all weather; bring sun or rain protection
Electric bikes available on request for easier riding
Type in your hotel/accommodation to see how far the attraction or departure point is.
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10/10 would recommend Alessio and the Tuscany Bike tours! We visited 2 castles (one of them a currently-operating hotel!) and finished off with a wonderfully made meal at a local restaurant/shop. Alessio was very knowledgeable and personable and we felt his passion for biking as we rode together. He definitely made the tour special and was accommodating with the booking dates as well. If you’re around the area, looking for a short and tour on a bike/e-bike, don’t look elsewhere.
An Unforgettable Day with Tuscany Bike Tours! Our day with Tuscany Bike Tours was absolutely unforgettable, and we cannot say enough good things about our incredible guide, Alessio. From the moment we met him, it was clear we were in the best hands. Alessio wasn’t just a guide — he was a true ambassador for Tuscany, combining deep local knowledge with an engaging personality and a genuine passion for sharing his beautiful region with others. Throughout the ride, Alessio took the time to get to know us personally, which made the experience feel warm and authentic rather than just a standard tour. He shared fascinating stories and insights about the history of the area, the wine-making and olive oil production processes, and countless other interesting facts that brought the Tuscan countryside to life. His enthusiasm was contagious, and his love for what he does made the entire day feel so special. The bike ride itself was absolutely breathtaking — a perfect mix of gentle hills, charming villages, and postcard-worthy vineyard views at every turn. Every stop along the way was thoughtfully planned and allowed us to truly soak in the beauty of Tuscany at a comfortable, enjoyable pace. To top it all off, the tour ended with the most delightful home-cooked meal at a picturesque farmhouse tucked away on a hill, overlooking the rolling vineyards and olive groves. The food, wine, and scenery created a magical atmosphere that we will never forget — it was the perfect ending to a perfect day. We honestly can’t thank Alessio enough for his time, care, and passion. His attention to detail and personal touch made this experience the highlight of our entire trip to Italy. If you’re visiting Tuscany, do yourself a favor and book a tour with Tuscany Bike Tours — you will not regret it! Grazie mille, Alessio, for an experience we will cherish forever!
This tour is a must when you visit Florence! The staff is knowledgeable, accommodating, and super fun to hang out with all day. We used e-bikes which made the actual biking even more pleasant. Lunch and wine at the castle was delicious and the views are breathtaking. I highly recommend especially if you want to see the wine country and get away from the noisy city for a few hours. Ask for Ben. You will not be disappointed :)
I had an amazing time on this bike tour! Our guide, Ben, was awesome — super knowledgeable, patient, and fun to ride with. The day started with a short van ride from the bike store to Castello Guidarrcino, a beautiful castle built in the 1100s where the ride begins and ends. The castle itself is worth seeing — really cool and full of history. The ride takes you through gorgeous Tuscan countryside and several small towns that are just incredible to pedal through. Most of the route is very manageable, even for beginners, but be prepared for one hill with an 18% grade. Thankfully, they offer van support if you need a boost on the climb, which is a nice safety net. Some riders showed up in full road cycling kits, while others were in completely normal clothes. You can do either, but don’t feel like you need to bring advanced gear — this isn’t the Tour de France, and the ride is very accessible no matter your outfit. One thing to note: there aren’t any official bathroom stops between leaving the bike store and returning for lunch, though there are a few discreet spots along the way if nature calls. The experience wrapped up with a fantastic lunch and wine tasting. The food and wine were excellent, and there’s also a winery shop where you can buy olive oil and wine — or even have it shipped internationally. Overall, it was an unforgettable experience. Beautiful countryside, a fun ride, great wine, and an outstanding guide. Highly recommend!
After fast paced tours of the Vatican, Colosseum, and a bus tour of Tuscany, this small intimate bike tour of Chianti was the perfect day for us and one of the best memories of our Italy trip. The roads and scenery were breathtaking, the ride itself was over undulating roads, our guide, Angus, did a great job of keeping the pace manageable, when someone got a flat the support van was there in several minutes to swap out the wheel and get us on our way again. There's one challenging hill about 3/4 of the way into the ride, no worries if it's too much for a beginner, or even more seasoned cyclists, the van will give you a lift to the top so you're able to finish the ride back to the winery. The tour of the winery was every bit as cool as the ride itself, lots of history, great wine paired with an exceptional lunch. These guys are the best, highly recommended if your looking for an active tour of Tuscany without being stuck on a tour bus all day.
