Private Bike Tours in Tuscany: Your Ride, Your Pace

Just you, your person (or people), and the best roads in Chianti — no waiting around, no compromises.

You’ve put real thought into this trip. You’ve picked the hotel, you know where you want to go, and you want a day in the Tuscan countryside that actually feels like yours. That’s exactly what a private one day bike tour in Tuscany with us is.

Every one of our tours — from the Chianti Wine Tasting ride to the Gelato tour, the Florence to San Gimignano downhill and Florence to Siena (both the longer and shorter versions) — can be reserved exclusively for your group of 2 to 4 people. Scroll down to see the full list of our tours.

Already know which of our tours you’d like to book? Send us an email by clicking the link below or contact us via Whats app:

 
 
 
 
  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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What Makes A Ride With Us Different

When you book privately, the day revolves around you. Want to spend a bit longer at the winery? Fine by us. Want to take the views in slowly rather than push the pace? That’s what we’re here for. You get the same routes, the same guides, the same quality — just without anyone else along for the ride.

All our guides have been leading rides through these hills for over 15 years. They know the roads, the producers, the stories. They also know what it’s like to experience Tuscany for the first time, because they’ve been there themselves — and they’ve never quite left.

How the Pricing Works

Any of our standard tours can be made entirely private for a flat Private Exclusivity Fee of €150, on top of the usual per-person price for whichever tour you choose.

So for example, if you and a partner book the Chianti Wine Tasting tour privately, you pay the standard per-rider price for two people, plus €150. That’s it — your own guide, your own vehicle, your own day.

Meeting Points in Florence

To get you out of the city and into the hills as quickly as possible, we meet at convenient points just outside Florence’s historic centre. Depending on where you’re staying, you’ll be looking at a short 10–15 minute walk or a quick taxi ride. We’ll share the exact details once we confirm your booking.

How to Book

We don’t use automated booking for private tours. These days matter, and we want to make sure everything is right before you commit.

Step 1 — Have a look through our tours listed below and see which one (or which combination) catches your eye.

Step 2 — Get in touch: via email with the link below, whats app through the “message us” button or the form on oiur contact page. Tell us a bit about who’s coming, what you’re celebrating if anything, and what kind of ride you’re after.

Step 3 — We will get back to you personally with availability and everything you need to know before the day.

  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

  Florence to Siena - easier bike ride - Fantastic 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... read more 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!

Excursion258752
May 26, 2026

  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

Frequently Asked Questions: Private Tuscany Bike Tours