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You move on between hotels every two days, and we transport your bags, so on our cycling holidays in Italy you don't need to carry a lot in your panniers and you're free to explore Italy. In-between days are a great opportunity for some local exploring, using our detailed maps and route notes as your guide while you are cycling in Italy on the quiet backroads. We've a wide range of cycling holidays in Italy - from easy, flat cycling through the Ventian vineyards, to an exhilarating tour of Chianti. Or perhaps you'd prefer a relaxing coastal route exploring the delights of Sicily? To find out more about any cycling holiday in Italy, simply follow the links below.
For full holiday details click on the appropriate cycling holiday. Italy offers a great selection of activity holidays, take a look at our activities section for further information or visit our cycling holidays section to find out how cycling in Italy with Headwater works.
Cycling holiday, Italy
Chianti : Secrets of San Gimignano Cycling
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Upper 2 bike cycling holiday (hotel-to-hotel). Departs spring, summer, autumn for 9 days (8 nights)
Accommodation: stylish/luxury, friendly/quirky, gastronomic food, swimming opportunities. Good for: art/culture/history, flora & fauna, wine discoveries.
Cycling holiday, Italy
Piedmont : Gastronomic Barolo Cycling
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2 bike cycling holiday (hotel-to-hotel). Departs summer, autumn for 9 days (8 nights)
Accommodation: stylish/luxury, gastronomic food, swimming opportunities. Good for: art/culture/history, wine discoveries.
Click for details of our tour only 'lite' holiday.
Cycling holiday, Italy
Sicily : Secrets of Sicily Cycling
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2 bike cycling holiday (hotel-to-hotel). Departs spring, autumn for 9 days (8 nights)
Accommodation: friendly/quirky, swimming opportunities. Good for: art/culture/history, flora & fauna, birdwatching.
Cycling holiday, Italy
Tuscany : Secrets of Siena Cycling
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2 bike cycling holiday (hotel-to-hotel). Departs spring, summer, autumn for 11 days (10 nights)
Accommodation: mid range, swimming opportunities. Good for: art/culture/history, wine discoveries.
Cycling holiday, Italy
Umbria : Perugia to Assisi Cycling
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2 bike cycling holiday (hotel-to-hotel). Departs spring, summer, autumn for 9 days (8 nights)
Accommodation: mid range, swimming opportunities. Good for: art/culture/history, flora & fauna, wine discoveries, local culture.
Cycling holiday, Italy
Venetia : Villas and Vineyards Cycling
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1 bike cycling holiday (hotel-to-hotel). Departs spring, summer, autumn for 9 days (8 nights)
Accommodation: friendly/quirky. Good for: art/culture/history, wine discoveries.
Didn't find the cycling holiday in Italy you were looking for? Try letting our Holiday Finder help you choose, or give our sales team a call on 1-800-567-6286. If you'd like to browse through our extensive range of cycling holidays why not order a copy of our free full colour brochure?