Chianti, Olive Oil & Gelato Tasting Family Bike Tour

Discover the heart of Tuscan cuisine through a delightful cycling adventure that celebrates three of Italy’s most beloved foods: world-famous Chianti wine, golden extra virgin olive oil, and artisan gelato crafted with passion and tradition. This gentle, family-friendly tour combines the joy of cycling through Tuscany’s countryside with authentic tastings of the region’s most iconic flavors. Unlike intensive cycling tours, this experience prioritizes discovery, education, and the simple pleasure of enjoying exceptional food in spectacular surroundings.

Price – €170 per person*

*minimum of two participants required

 
 
 
 
  EXCELLENT  
  
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 Ron Vaughn 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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!!!
  
 
  
 
 
 
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 Paige Van Slooten 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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 
 
 
 
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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.
  
 
  
 
 
 
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 Alex Lenz 
 
 
 
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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..
  
 
  
 
 
 
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 Lesley Reller 
 
 
 
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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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Tour Details

• Distance: 15-20 kilometers (9-12 miles) downhill
• Duration: Full day including tastings
• Difficulty: Easy, suitable for anyone comfortable riding on the road
• Group Size: Small groups of 2-8 for personalized attention
• Terrain: Mostly gentle descent with a couple of flat sections
• Meeting Point: Florence (pick up at another location can be arranged on request)

Cycling Through Culinary Paradise

Your journey begins in picture perfect Castellina In Chianti. We ride on peaceful country roads that wind through the very landscapes where these treasured ingredients are born. Pedal past ancient olive groves where silver-green leaves shimmer in the Tuscan sun, cruise alongside prestigious vineyards that have produced world-class wines for centuries, and enjoy the gentle rhythm of cycling through working farms and traditional countryside. The carefully planned route takes advantage of natural topography, featuring a gentle descent that make cycling effortless and enjoyable.

The First Treasure: Artisan Gelato

We do our gelato tasting at a beloved local gelateria where master artisans create exceptional gelato using traditional methods passed down through generations. Watch skilled gelato makers at work, learn about the difference between authentic Italian gelato and mass-produced alternatives, and sample flavors that showcase the best of Tuscan ingredients.

From classic favorites like rich pistachio and creamy stracciatella to seasonal specialties featuring local honey, fresh fruits, or even Vin Santo dessert wine, each spoonful represents the artistry and passion that defines authentic Italian food culture.

The Second Treasure: Liquid Gold

Experience the magic of Tuscan olive oil production at a working farm where they produce some of Italy’s finest extra virgin olive oil. Learn about the delicate timing required for harvest, the traditional pressing methods that preserve maximum flavor, and the characteristics that distinguish exceptional olive oil from ordinary varieties.

Taste oils with different flavor profiles while your guide explains the nuances that have earned Tuscan olive oil the nickname “liquid gold.” Discover how to identify quality oil and understand why this simple ingredient forms the foundation of Mediterranean cuisine.

The Third Treasure: Chianti Wine Heritage

Complete your culinary trilogy with a visit to a family-owned vineyard where passionate winemakers share their craft and stories. Learn about the specific grape varieties that create Chianti Classico’s distinctive character, the traditional methods that have evolved over centuries, and the deep connection between terroir and flavor.

Taste carefully selected wines while enjoying panoramic views of the vineyards that produced them. Your hosts share insights into food pairing, proper tasting techniques, and the cultural significance of wine in Tuscan daily life.

Educational and Entertaining

Throughout your journey, our knowledgeable guides share fascinating stories about Tuscan food culture, traditional production methods, and the families who have preserved these artisanal traditions. Learn about seasonal cycles, sustainable farming practices, and how modern techniques enhance rather than replace time-honored methods.

This isn’t just tasting but genuine education about the passion, skill, and patience required to create these exceptional products. Children discover where their food comes from, while adults gain deeper appreciation for artisanal craftsmanship.

What’s Included

• Comfortable hybrid bicycles suitable for all ages
• Professional helmets and safety equipment
• Expert English-speaking guide
• Authentic gelato tasting at local artisan shop
• Extra virgin olive oil tasting
• Chianti wine tasting at one of our favourite local vineyard
• Educational insights into traditional production methods
• Van support

If this tour sounds great but you don’t have many or any wine drinkers in your group, why not do our Gelato Tasting Bike Tour?

  Top notch service for cyclists! - Wonderful experience riding all over the countryside with 4 friends. The guides were punctual, professional and were able to adapt last minute to allow us more riding than we originally... read more planned. Highly recommend them!

Viktoria K
May 7, 2026

  Highlight of Tuscany - Our 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... read more 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.

Karen P
November 9, 2025

  An amazing tour with the BEST guides! - What 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... read more with them today. We will definitely be returning and bringing more friends!

Karin M
October 6, 2025