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Our Italian cycling holidays in conjunction with Headwater explore corners of the country you might miss when travelling by car or train. Bike through postcard-perfect landscapes with plenty of stops along the way, including city trips and wine tastings.

You’ll be given a bike that suits you (or you can bring your own if you prefer) - see our individual itineraries for details of what else is included, from route maps and GPS navigation, to Headwater's convenient wine-carrying service. 

Cycling tours are marked out of five for difficulty, so keep an eye out for the rating. Some are made for casual riders, while others suit more experienced cyclists. 

Choose your itinerary

Travel through the vineyards and foodie towns of Piedmont, with stays at beautiful, historic hotels along the way.  

Pedal along Chianti's wine route and tick off Tuscan towns like San Gimignano, Siena and Volterra on our Classic Tuscany cycling holiday.

 

Explore Umbria's hill towns, vineyards and sunflower fields by bike on this nine-day itinerary.

Stay in a farmhouse hotel and spend your days cycling through the meadows and vineyards of the Venetian Plain.