Private Bike Tour & Chianti Wine Tasting in Tuscany
Overview
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A full-day cycling tour from Florence into the enchanting Chianti region promises a delightful escape into the Tuscan countryside. Pedal along serene country roads surrounded by cypress trees, vineyards, and olive groves, while stopping at local wineries for three tastings. This small-group tour ensures a personalized experience, complete with a light Tuscan lunch. Enjoy the rich history, food, and wine of Tuscany as you explore picturesque hilltop towns and earn your gelato or pasta along the way.
- Discover the scenic Chianti region on a guided cycling tour
- Enjoy two wine tastings and a light Tuscan lunch included
- Small groups for a personalized experience (max 8 people)
- Expert insights into local culture, history, and cuisine
Additional Info
Public transportation options are available nearby
Not recommended for travelers with spinal injuries
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Travelers should have at least a moderate level of physical fitness
What To Expect
Fonterutoli
Dating back from 998 this village is home to the Mazzei family and is famous as the meeting point of the knights in the race between Florence and Siena (ask your guide!)
Castellina In Chianti
Certainly one of the most picturesque of the Chianti towns, this hill top gem gives you a chance to have a stroll, soak in the atmosphere and perhaps top up your espresso levels or have a second breakfast
Options
Private Bike Tour & Chianti Wine Tasting in Tuscany
What‘s Included
Wine Tasting of Chianti and other Tuscan wines in two wineries
Bottled water
Alight Tuscan lunch will be provided during the ride along with your second wine tasting
Use of bicycle
Coffee and/or Tea
Snacks
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
26 reviews
Total reviews and rating from Viator & Tripadvisor
Florence to Siena - easier bike ride
Excursion258752,May 26, 2026
- Review from Tripadvisor
5.00Fantastic family experience! My family of 4 (two teenagers and two adults) enjoyed the amazing Italian countryside scenery and experience of being in small towns outside of Florence to our destination of Siena. Chris Small was a fabulous guide who gave us insight into the culture and history of the area and ensured each of us had a memorable time! Highly recommend to anyone especially families wanting special memories together! Would love to do this again!
Highlight of Our Honeymoon - Don't Miss Out
meganwO5163FQ,Nov 29, 2025
- Review from Tripadvisor
5.00We truly can’t say enough wonderful things about this experience! Biking through Tuscany ended up being the absolute highlight of our honeymoon. From the incredible hospitality of our guide, Chris, to the welcoming staff at each wine tasting stop, every detail made the day unforgettable. The scenery was breathtaking, the wine was amazing, and the whole experience felt so thoughtfully curated. I’ll be recommending this adventure to everyone I know traveling to Tuscany. Fair warning though, this tour has completely ruined store-bought olive oil for us!
Highlight of Tuscany
karenpA3932CL,Nov 9, 2025
- Review from Tripadvisor
5.00Our experience on this bike tour just could not have been any better. My husband and I opted for the Florence to Siena "soft tour" which is 13 miles long. Chris, our guide was exceptional in every way. He not only transported us from Florence and then from Siena, but he was very informative, explanatory and personable. He went out of his way to make us feel comfortable and informed. The ride itself covered breathtaking terrain and even included a stop at a winery. Do not hesitate to sign up for any of the bike ours offered by this group - you won't regret it.
A worthwhile experience
P4855JSjacobk,Oct 13, 2025
- Review from Tripadvisor
5.00We had an incredible day on this tour. It was truly the highlight of our two week trip across Italy. Chris gave us his personal attention throughout the day, even supplying us with rain jackets when the weather briefly took a turn for the worst. He was an absolute treasure trove of knowledge on a wide-range of subjects: the history of the region, cycling, the food and, of course, the wine. Better yet, he was great company and very easy to talk to. It was clear he puts a painstaking amount of attention to detail in planning out and customizing the various tours he offers. If you're looking for a fun way to get out of the city and experience the Tuscan wine country, I can't recommend this tour enough. It was well worth the time and money.
Wonderful Cycling Week in Tuscany
Scenic48552801541,Oct 10, 2025
- Review from Tripadvisor
5.00My wife and I had a wonderful 7 day cycling vacation in Tuscany, thanks in large part to Chris. Everything was well planned - lodging, biking routes, and of course the food. Chris was an excellent host and guide for the week. He is extremely knowledgeable about theTuscany region and an avid cycling enthusiast. He shares this expertise in an enthusiastic and humourous way that enriches the entire experience.
Incredible experience - just book it!
655christyr,Oct 8, 2025
- Review from Tripadvisor
5.00We are a group of 3 couples who love to do fun experiences when traveling together. We booked the Private Bike Tour & Chianti Wine Tasting in Tuscany tour for mid-September and had the absolute best time! Our guides, Chris and Francisco, were some of the best guides we've ever had! They were so knowledgeable and so much fun at the same time. They were perfect and gauging our group and provided the best experience. Each of our wine stops was unique. We absolutely loved the stop at Cantine Guidi in Chianti Classico - the lunch was simply amazing along with the staff at the winery. One of the owners even spent time with our groups while we lunched - we felt so lucky! The other stop that we loved was at Fattoria Montecchio - it was incredibly beautiful and the wine, cheese, olive oil was so delicious. If you're considering this company/tour, book it! It was one of the highlights of our trip in Italy!
Private cycling tour of Tuscany / Chianti
mrsasser,Oct 6, 2025
- Review from Tripadvisor
5.00Chris did an awesome job organizing the cycling tour! His wealth of local knowledge and captivating storytelling kept us entertained throughout. He is incredibly familiar with the roads and knows the best cafe stops. Great experience overall, I highly recommend the experience!
An amazing tour with the BEST guides!
karinm416,Oct 6, 2025
- Review from Tripadvisor
5.00What an amazing tour! Tuscany Cycling Tours really know their stuff. The guides were so friendly and knowledgeable and anticipated all of our needs. Incredible. Stop shopping around and book with them today. We will definitely be returning and bringing more friends!
Views, climbs, wine & fun
PollPeartravels,Oct 5, 2025
- Review from Tripadvisor
5.00Chris set up beautiful, challenging rides with great coffee stops. Dinners were special & great conversation! Highly recommend
Awesome Tuscon E-bike Tour!!
343curty,Oct 1, 2025
- Review from Tripadvisor
5.00Our recent e-bike tour with Chris through the Tuscan countryside was amazing and one of the highlights of our 2-week stay in Italy!! Chirs was a perfect guide -- prompt, very engaging and informative about the area and helpful in leading us along our tour route -- and the e-bikes and equipment were top-notch. The itinerary included a short tour in Gaiole in Chianti, a Ricasoli wine tasting, and lunch at a stunning hilltop restaurant that rates as one of the best meals of our trip. Thanks again for a great adventure Chris -- memories of riding through scenic Tuscan vineyards and olive groves will stay with us for a long time!!
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Operated by Tuscany Cycling Tours