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Tuscany Bike Tours

Explore Italy’s pedaling paradise! Cycle through the heart of Tuscany on bike tours with local guides.
Cycling trips
The best of road biking in Tuscany
MTB tours
Off-road rides on scenic trails
Friends toasting together at dinner
Food & wine tours
Savor the scenery & flavors of Italy
Self-guided trips
Pedal at your own pace
Cycling trips
The best of road biking in Tuscany
Explore adventures
MTB tours
Off-road rides on scenic trails
Explore adventures
Friends toasting together at dinner
Food & wine tours
Savor the scenery & flavors of Italy
Explore adventures
Self-guided trips
Pedal at your own pace
Explore adventures
Worldwide adventures with the best local guides
Unique adventures
Certified local guides
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All bike tours in Tuscany

Lorna

All aspects of the cycling tour were excellent from the initial contact and followup emails back and forth in the months preceding our trip to the details provided at the very start of the trip in San Gimignano. Instructions were clear and the self guided maps and information provided were accurate and relatively easy to follow. Great bikes! Solid, easy to ride and well tuned. We were surprised somewhat to see that the tires provided were slicks instead of tires with some tread. We were a little concerned on the first day when it rained that the roads would be slippery but it wasn’t an issue. Overall, yes, good value for the money.

Gary

I would not hesitate to recommend your cycling holidays – its a mix of orienteering and cycle touring and its really a hell of a lot of fun. Sometimes you work hard – then you coast downhill for a beer. And all the way, awesome views of Tuscany. It was just absolutely fantastic.

Elaine

Didn’t have to worry about the logistics, just cycling and eating! This route took us to places we would not normally have visited on a standard tourist route in Italy and allowed us to meet the locals and see aspects of Italian life outside of the main tourist areas. Overall standard of accommodation was a pleasant surprise and pleased so many had pools. Our guide was really excellent; she was friendly, professional and knowledgeable about the route and places to visit on the way. Didn’t have to worry about the logistics, just cycling and eating!

Robert T

I wanted to thank you all for the wonderful self-guided bike tour my wife and I did 2 weeks ago. I loved every second of it. The bikes were incredible and the directions were so easy to follow. The routes were great and the hotels were amazing. We look forward to riding with Cicloposse again next year.

Mark and Julie

I would like to thank you for a fantastic trip that you organised for Julie and myself in may last year We have been telling everyone how much fun we had so don’t be surprised if you get a few more Australian enquiries Hope you both have a great year

Kathy and Rick P.

Rick and I just arrived back in the USA and wanted to take a moment to let you know that we had a wonderful Gravel Bike Trip. We thank you for the extraordinary job organizing, responding and planning the tour. The hotels were lovely and everyone was so helpful. Your Bike Trip Handbook was very helpful and will be a treasured souvenir from our trips. We will definitely look into taking another bike tour with your company and have already passed the word on to many of our friends and relatives. Maybe Sardinia! We do not have Instagram but will share our five star rating on sites listed. It was great working with you and I wish you the best with your tours this Summer. Thanks Again.

Carolyn Hayes

This was a fabulous experience in every sense – majestic 13th century towns, incredible vistas, wonderful caring guides, amazing farmhouse accomodation, a world class chef, a genuine family with local knowledge and a generous spirit wanting you to feel and live the Tuscan way.
We felt like we had the privilege to be brought into their world and didn’t want to leave. The cycling was outstanding and cooking lessons encouraging and informative – I highly recommend you do this!

Scott Vold

Amazing trip and experience. Top shelf production from start to finish – guides, terrain, equipment, food, lodging…all far exceeded my expectations. Already dreaming of returning….

Sarah

What an opportunity to see the Tuscan countryside in such an intimate way as cycling / mountain biking. How else could we get a guided tour – the best trails, lodging and meals all figured out for us?

When one guest lacked stamina the first day, Skedaddle got him an e-bike and for the rest of the days he did great. When another guest needed stitches a guide took her to the hospital in the van right away. These are examples of good service.

Your taste of Tuscany, on two wheels

Sensory overload, in the best possible way

Famed for its wine and vistas, Tuscany houses some of the most scenic bike rides in the world. Cruise through iconic rolling hills & vineyards cradled by sunshine. Immerse yourself in charming medieval villages and savor the region’s legendary cuisine and Chianti wines. Breathe in the beauty, history, and deliciousness of Tuscany – all at your own pace, on two wheels.

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Landscape in Val d'Orcia (Tuscany) with bicycle
Woman cycling in Rio Nell` Elba on the Island of Elba

Pedal, sip, savor: the best of Tuscan biking

Seasoned local guides

    • With expert local guides, you’ll never miss a scenic trail, an epic panorama, or a great restaurant.

Hassle-free logistics

    • Leave the boring stuff to us — we take care of the logistics, you enjoy the journey!

Itineraries to fit all needs

    • Guided or self-guided, cycling or MTB, beginner or advanced — you’ll find it all here!
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Best areas for bike tours in Tuscany

Chianti

In Chianti, you’ll glide through sun-drenched vineyards, quintessential medieval villages, and rolling hills that define Tuscany’s postcard-perfect beauty. Afterwards, reward yourself with world-famous wines and exquisite local cuisine.

Crete Senesi

If you want a more adventurous route, head to the unique clay roads of the Crete Senesi. Here, you can discover hidden medieval gems, explore lunar-like terrain, and indulge in the region’s prized Brunello di Montalcino wines.

Val d’Orcia

UNESCO-protected landscapes unfold among Val d’Orcia’s cypress-lined roads, charming hilltop towns, and golden stone farmhouses. Immerse yourself in the region’s tranquility and savor its unique flavors – from creamy pecorino cheese to hearty pappardelle pasta dishes.

Tuscany bike riders shadow

Frequently asked questions about Tuscany bike tours

  • Tuscany is absolutely fantastic for road cycling.

    First off, Tuscany has varied terrain, from gentle rolling hills to challenging climbs. There are bike tours in Tuscany, Italy, to suit all cyclists, from beginners to experienced riders. Also, the scenery is spectacular – cyclists can enjoy stunning views of vineyards, olive groves, and medieval towns as they ride.

    Tuscany has a strong cycling culture, and there are many cycling events and festivals held throughout the year. The fantastic food and wine you can enjoy off the trails are just a bonus!

  • Absolutely! Cycling and visiting wineries are two of the most popular activities in Tuscany, and combining them makes for an unforgettable experience. The rolling hills of Tuscany are perfect for cycling, and many wineries are located along scenic country roads.

    However, make sure to factor in the effects of wine tasting on your cycling ability. It is important to drink responsibly and to avoid cycling after consuming too much alcohol.

  • While the region of Tuscany is very bike-friendly and Tuscan bike tours are world-famous for a reason, Florence’s bikeability is a mixed bag. Here’s our list of pros and cons:

    + Growing infrastructure: Florence is investing in cycling infrastructure, with over 90km of bike paths currently available and plenty of plans to add more.
    + Flat areas: The historic center of Florence is relatively flat and easy to bike around. Many streets are closed to car traffic, creating pedestrian and bike-friendly zones.
    + Bike rentals: There are plenty of bike rental places in Florence, making it a convenient option for visitors.

    – Limited bike lanes: Many streets in Florence, especially outside the center, lack designated bike lanes, making you cycle alongside scooters and cars.
    – Cobblestones: Many streets in the historic center are lined with cobblestone, which can be bumpy and uncomfortable to cycle on.
    – Hilliness: While the center is flat, there are some hilly areas around Florence, which can be challenging for less fit cyclists.

Get in touch
We’re happy to answer any of your questions. Send us an inquiry or talk to one of our adventure planners free of charge.
Get in touch
We're happy to answer any of your questions. Send us an inquiry or talk to one of our adventure planners free of charge.
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