Tuscany Bicycle Tours

Pedal the romantic hills of central Italy.

Review Standard Itineraries

Browse our most popular itineraries, visiting the most desirable sites in the region.


Request Custom Tour Proposal

If you prefer to have a special tour a different from our standard itineraries, request a custom tour.


Food, wine, culture, and romance.  What else could be on your wish list for a cycling tour? On our Tuscany bike tours every town has its own rich history and secrets for you and your loved ones to discover.  And the food… oh the food.  Even the most low-key restaurants have amazing delectable food.

All of our Tuscany bike tours are private custom self-guided tours, where you can name the dates, riding distance, and other details of your tour. You have worry-free routing by GPS, and a guide/concierge always available to help you when you need it.

Your begin in Florence and pedal through well-known areas and towns within the region: Chianti, San Gimignano, and Siena.  Longer tours include rides and stays in Montepulciano,  Montalcino, and Cortona.

As with all of our self-guided bike tours, we offer something for everyone—from relaxed options that can be completed on e-bikes or hybrid bikes, to aggressive routes for avid cyclists on road bikes.  Our suggested itineraries range from 4 to 10 nights, or we can custom design a tour for you.

Our tours in Tuscany are Self-Guided, but if you prefer a Guided Tour in Tuscany we can organize a custom guided road and mountain bike tour for you!  Please contact us if you are interested!

For general information on how our Self-Guided Tours work, please click HERE. Also, discover more about how we create our self-guided bike tours so that they are the best available by reading this blog post.

Join us on one of our Tuscany Bike Tours!



“We thoroughly enjoyed every aspect of this tour – well thought out bike routes, very good hotel accommodations (nice, clean rooms and substantial breakfasts), and excellent choice of breweries and brewery restaurants (including brewery tours when available). It was obvious that a great deal of attention to detail had been given to this tour and customer service and client satisfaction was of ut… Read more




San Gimignano







Let us Start Curating Your Cycling Vacation!

Contact Us

USA & Canada: +1-877-275-9241

International: +1-415-322-0421

Email: info@outfittertours.com

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