A cyclist in Tuscany views the hills of Chianti from their bike

Exploration between the landmarks

We came to this region twenty years ago and never left. Since then, we’ve mapped the most photogenic routes, guiding curious travellers to the places where history, vines, and vistas meet. From the crisp air of the Chianti hills to the deep notes of a Riserva, let us show you the Tuscany you came to find.

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Our One Day Bike Tours

Wine Tasting & Bike Tour

Visit two typical Tuscan villages as you pedal through Tuscany’s most famous wine region with three wine tastings & a light tuscan lunch on Chianti Classico’s best roads.

Gelato Tasting & Bike Tour

Learn how gelato is made, & enjoy a gelato tasting, followed by a gentle ride through the countryside and finish with a visit of San Gimignano & perhaps another gelato!

Florence to San Gimignano

Cruise down a quiet and gorgeous 12 mile downhill before seeing Tuscany’s Manhattan of The Middle Ages San Gimignano. Then finish with a Chianti wine and olive oil tasting.

Florence to Siena

Choose the 10 mile or the more challenging 16 mile version and either way end the day with free time to explore and have lunch in the Tuscan gem that is the hill top town of Siena.

Chianti Road Cycling

Want a bit more of a challenge? Have you always dreamed of tackling Tuscany’s famous hills on the way up and down? Then this tour is for you!

Wine, Olive Oil & Gelato

Learn how gelato is made, enjoy a wine and olive oil tasting in a beautiful vineyard in the heart of Chianti and visit the picturesque town of San Gimignano

Tuscany By E Bike

Effortless riding around the Chianti Classico on an ebike? Check. Wine tasting with a light Tuscan lunch? Yes. Pedal through Tuscany without breaking a sweat. Nice.

Ride & Cooking Class

A spectacular ride starts your day and then you get to learn how to make an authentic italian two course lunch and enjoy a wine tasting at the same time. Buon appetito!

Coming soon…

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      EXCELLENT  
   Based on 50 reviews 
    
 
 
 
   
 
 
       Posted on Google  
   
   Ron Vaughn 
 
 
 
 Trustindex verifies that the original source of the review is Google. Would 100% ride with this team again. My son and I signed up for a ride. I didn't know it but I was having pre-migraine issues, and I fell apart after about 5 miles. The host completely took care of me and pampered me (I got ride in the support van) and my son had an amazing ride.  These guys are great bikers, know the area better than anyone, and tell amazing bike stories. We felt like we were being hosted by the local pros. I wouldn't go with anyone else.
  
 
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   Nicole Schmidt 
 
 
 
 Trustindex verifies that the original source of the review is Google. This summer my daughter and I spent a day cycling with Jason. It was, by far, the highlight of our trip to Italy. We were looking for a strenuous ride that included gelato, wine tasting and lunch, and as much of Tuscany as we could see in a day. Jason took our preferences into consideration and created the perfect ride. He picked us up at the train station, drove us an hour through the beautiful Tuscan countryside to our starting point, fitted our bikes (good quality and in perfect condition) and helmets and then paid close attention throughout the entire trip to be sure we were having fun, staying hydrated, and getting the most out of the ride. He took pictures and videos which he sent to us the next day. The wine tasting was a blast, and the food delicious. At the end, he dropped us near our hotel. I cannot imagine spending a better day in the region. We would definitely do this trip again and are recommending it to our friends. It's rare to find a competent guide who will create a custom trip with total flexibility throughout--especially for the price. You won't find a better option in Italy. And if you are thinking you might just rent bikes and head into the countryside on your own--do not do it! Hire an expert--it will be the highlight of your trip too!
  
 
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   Kenzie Imhoff 
 
 
 
 Trustindex verifies that the original source of the review is Google. Had an amazing day biking from Florence to Siena with Tuscany Cycling Tours! From the start to the end of the trip, everything was so intentional, customized and beautiful. For example, they picked me up right by the hotel in Florence in the morning and we drove to a small town in the Chianti area, San Donato, where I started the bike. The car follows you the whole time to make sure you know where you’re going. Then, you stop in Castellina where you get thirty minutes to explore the cute town. Finally, you bike through vineyards until arriving outside of Siena where the car then drives you the rest of the way and you get three hours to independently explore the city. In total, it is about three hours of biking and it is completely manageable for all levels: you set the pace. On the way back, you return in car enjoying the views and conversation. Overall, I would highly recommend the tour as it is a much more personalized way to explore the Chianti area and Siena: when you arrive to Siena, you have a greater context to the surrounding area, enjoying your glass of wine with a more profound understanding of where it comes from. Also, Tuscany Cycling Tours was super proactive, communicative and kind, making the whole experience extremely smooth and enjoyable!
  
 
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   Bethany Gorter 
 
 
 
 Trustindex verifies that the original source of the review is Google. We went on a day bike trip in tuscany with 8 family members for my parents anniversary and had SUCH an amazing time with Chris and Jason. Chris tailored the trip perfectly to our families needs and planned such an amazing route. 100% would book with him again and was genuinely the highlight of my Italy trip. Bikes were in great condition and the electric option was great for my family. Thank you Chris!!!
  
 
      Posted on Google  
   
   Paige Van Slooten 
 
 
 
 Trustindex verifies that the original source of the review is Google. Tuscany Cycling tours is the absolute best. I highly recommend you booking this tour. You will not be disappointed. The guides give you so much information about the area and want to make your experience the absolute best. We couldn’t have had a better day cycling through the vineyards and the beautiful hillside of Tuscany. We loved the gelato stop and also touring the big castle on the hill. My kids said it was the best day ever! Thank you Tuscany cycling tours! We will be back next time we are in Italy!
  
 
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   Kris Arnheim 
 
 
 
 Trustindex verifies that the original source of the review is Google. Our family bike tour with Tuscany Cycling Tours was truly the highlight of our trip to Italy! We were traveling with our three kids (ages 17, 15, and 12), and it ended up being everyone's favorite day of the vacation. Chris and the entire team were incredibly knowledgeable, friendly, and fun, making us feel comfortable from the moment we arrived. The ride through the breathtaking Tuscan countryside was absolutely stunning. We loved stopping in charming little towns along the way, and the visit to the winery was the perfect addition to an already unforgettable experience. The pace was great for our family, and the tour offered the perfect mix of beautiful scenery, local history, culture, and fun. It was such a unique way to experience Tuscany that we never would have discovered on our own. If you're visiting Florence, don't hesitate to book with Tuscany Cycling Tours. It was worth every penny, and we'd recommend it to anyone looking for an authentic, memorable, and incredibly enjoyable day in Tuscany. Thank you, Chris and team, for giving our family memories we'll cherish forever!
  
 
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   Stefan Ball 
 
 
 
 Trustindex verifies that the original source of the review is Google. The ride was very beautiful and a highlight of my trip. Chris was a great guy to ride with and explained a lot about the area. I would definitely come back to ride for a longer trip since I only did a day ride.
  
 
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   Maya Lopatynsky 
 
 
 
 Trustindex verifies that the original source of the review is Google. We did a private hybrid e‑bike tour with Tuscany Cycling Tours in the middle of our 8‑day Italy trip (Rome, Florence, and Venice), and it ended up being the highlight of the entire vacation. Chris picked us up in Florence and drove us out to a small Chianti town for cappuccinos before we started riding, which immediately made the day feel relaxed and personal. On the bikes, he was incredibly patient with us as beginners, always checking in on how we were doing and adjusting the pace so we could really enjoy the views. He shared stories about past multi‑week cycling trips he has led, pointed out historic villas that have been there for over 200 years, and taught us about local life and traditions along the way. The route itself was stunning – rolling hills, vineyards, and classic Tuscan vistas that look like a postcard. He also brought us to a small family‑run winery for a tasting and lunch, which was honestly the best meal of our trip (the ragu was unforgettable). We loved it so much that we ended up buying a full case (24 bottles) to ship home to the US. The whole experience felt curated, thoughtful, and never rushed. If you’re looking for a memorable way to experience the Tuscan countryside, I can’t recommend Tuscany Cycling Tours and Chris enough. We’re already talking about coming back to do a longer multi‑day cycling trip with him in the future.
  
 
      Posted on Google  
   
   Alex Lenz 
 
 
 
 Trustindex verifies that the original source of the review is Google. A fantastic experience that we recommend! Family of 5 with 3 older kids/young adults. We booked an e-bike tour of Tuscany with Chris & Jason. One of our kids doesn't ride much and the guys were awesome getting him up to speed and feeling comfortable on the bike. The tour itself was phenomenal. They picked us up at our hotel and we drove about 45 minutes outside of Florence. We rode for a couple of hours (with strategic view/rest stops) and around noon we rolled into a private family vineyard where the owner hosted us for lunch and a wine tasting. We also had the opportunity to buy some wine and olive oil directly from Guid 1929 (name of vineyard) before we left. Amazing. To wrap up, we rode back to almost our starting point and our capstone was homemade gelato from a local shop. All-in-all, arguably the best day on our trip, and the pictures/drone video that were sent to us afterwards make for a great memory. Bonus, we didn't use our screens basically the entire day. I'm looking forward to doing another trip with Tuscany Cycling Tours..
  
 
      Posted on Google  
   
   Lesley Reller 
 
 
 
 Trustindex verifies that the original source of the review is Google. This tour was a highlight of our trip to Italy! We enjoyed all 3 stops and Chris was so entertaining and informative! Highly recommend riding through the hills of Tuscany. It was memorable!
  
 
  
  
 
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Discover Tuscany by Bike

Welcome to Tuscany Cycling Tours, your gateway to the most beautiful bike rides in Italy. Based in Florence and run by experts with over 30 years of combined experience, we offer unforgettable one-day bike tours through the rolling hills, vineyards, and medieval villages of Tuscany. Whether you’re looking for a leisurely Chianti bike tour with wine tasting or a more challenging cycling adventure, our guided tours are the perfect way to experience the heart of Tuscany.

Join us for a day you’ll never forget—pedal past olive groves, stop at historic wineries, and explore hidden corners of the Tuscan countryside with a guide who knows the roads like the back of their hand. Our Tuscany bike tours are designed for all levels of riders and start less than an hour’s drive from Florence.

					  Wonderful Cycling Week in Tuscany - My 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... read more 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.				
Scenic48552801541
October 10, 2025 

					  Views, climbs, wine & fun - Chris set up beautiful, challenging rides with great coffee stops. Dinners were special & great conversation! Highly recommend				
PollPeartravels
October 5, 2025 

					  Highlight of Our Honeymoon - Don't Miss Out - We 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,... read more 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!				
Megan T
November 29, 2025 

Why Choose Us?

Over 30 years of Bike Tour Experience

Our two founders have a combined three decades of taking happy guests on bike tours in Tuscany as well as all over Italy from the Dolomites to Puglia. Over the years we have served thousands of happy guests, and received hundreds of five star reviews and now we bring all that together for your cycling tour in Tuscany!

The Best One Day Bike Tours From Florence

We aim to give you the best experience on your ride in Chianti with us. Whether it’s a gentle cruise and a gelato at the end or a more challenging custom road bike tour, we can make a memorable day on two wheels in Tuscany. Get in touch and tell us what your perfect Tuscan bike ride would be like…