Florence to Siena Bike Tour: An Epic Journey Through Renaissance Tuscany

Embark on an extraordinary cycling adventure between two of Italy’s most magnificent cities. You will traverse the legendary landscapes of Chianti while experiencing the transition from Renaissance Florence to medieval Siena. This remarkable point-to-point journey offers two distinct experiences designed to accommodate different cycling preferences and abilities. Whether you choose the full challenge or the shorter version, you’ll witness some of Tuscany’s most spectacular countryside, connecting two UNESCO World Heritage cities through the timeless beauty of rural Italy.

Price – €160 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 Full Version: 28 kilometers (17 miles)
• Distance Short Version: 18 kilometers (11 miles)
• Duration: Full day
• Difficulty Full Version: Challenging with a climb of 230m/750 feet gain over 10km/6 miles
• Difficulty Short Version: Easy to moderate, rolling terrain and downhill with one climb of less than a mile
• Group Size: Small groups of 2-8 for personalized attention
• Transportation: Return transfer from Florence included (a pickup at your hotel/villa in another location can be arranged by request)
• Free Time: 3 hours for independent Siena exploration

The Challenge Route: Florence to Siena

For experienced cyclists seeking an authentic adventure. The full 28 kilometer route delivers an unforgettable day of cycling through diverse Tuscan terrain. Departing from Florence by van, we drive into the rolling hills of Chianti and begin the ride in San Donato. After a few minutes to wander around this charming hill top village, we embark on the challenging climb to Castellina in Chianti.

Once in Castellina we have some free time for an espresso, cappuccino or a cold drink and perhaps the famous cyclists’ second breakfast. There’s more riding after this as our route follows closely the Romea Senese. The ancient pilgrim’s trail from Florence to Siena. We stop for a photo by the legendary town of Fonterutoli. The alleged meeting place of the famous knight’s race between Florence and Siena. Ask your guide to know more!

The final part of the ride gets us to within sight of Siena’s ancient walls. Where we jump back in the van for a final 5 minute transfer to the edge of the historic centre.

The Soft Route: Scenic Cycling with Wine Tasting!

Perfect for recreational cyclists, families, or those preferring a more relaxed pace. The shorter version covers 18 kilometers of the most beautiful section of the full ride while we skip the long climb. This gives us a little extra time so later in the day we will stop for a quick (2 glass) wine tasting. There we get some insight into Chianti wine, its production and place in this region.

You’ll still experience the magic of cycling through Chianti’s vineyards. Stopping in charming Castellina in Chianti, and having free time in Siena’s historic center.

Discovering Siena’s Medieval Splendor

Both routes conclude with up to 3 hours to explore Siena independently, one of Europe’s best-preserved medieval cities. Wander the fan-shaped Piazza del Campo, where the famous Palio horse race has taken place twice yearly since 1644. Climb the Torre del Mangia for panoramic views across the Tuscan hills you’ve just conquered. Or visit the magnificent Gothic cathedral with its intricate marble facades and Renaissance artwork.

Siena’s winding streets reveal hidden treasures at every turn—artisan workshops, and traditional trattorias. Explore the different Contrade (or areas of the city) that compete in the Palio. There are 17 in total, can you find them all..?

Cultural Insights Along the Way

Throughout your journey, discover the stories that shaped this legendary landscape. Learn about the ancient rivalry between Florence and Siena and the strategic importance of hilltop towns. How centuries of careful cultivation created the harmonious blend of agriculture and architecture that defines Chianti today.

Your knowledgeable guide shares fascinating insights about local wine production, traditional farming methods, and the cultural significance of the places you encounter. These stories transform your cycling experience into a deeper understanding of Tuscan life and history.

What’s Included

• High-quality hybrid bicycle
• Expert English-speaking guide
• Professional helmet and safety equipment
• Scenic photo stops and cultural commentary
• Return transportation from Siena to Florence
• Full van support throughout the tour
• Recommendations for Siena exploration

Is the longer version of our Florence to Siena Tour not challenging enough for you? Then you should check out our One Day Road Cycling Tour in Chianti instead!

  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

  Incredible experience - just book it! - We 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... read more 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!

Christy R
October 8, 2025

  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