Cycling in Italy

Here is our range of cycling holidays in Italy

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
Treasures of Tuscany
Location:Tuscany, Italy.
Holiday type:Independent cycling, hotel-to-hotel.
Managed locally by Headwater employed rep.
Activity level: 2 bikes
Duration:9 days (8 nights)
Hotels:Mid range/good value
Meals:Continental breakfast and 6 evening meals.
Prices from:Please call.
Departs:Every two days from 01 May 2010 to 16 Oct 2010
  JFMAMJJASOND
Good for:Wine tasing Swimming opportunities Art and history Local culture Choices for children
Cycling in Italy: Treasures of Tuscany


Cycling holiday, Italy
Heart of Venetia Cycling
Location:Venetia, Italy.
Holiday type:Independent cycling, single centre.
Managed locally by Headwater employed rep.
Activity level: 1 bike
Duration:8 days (7 nights)
Hotels:Mid range/good value, friendly/quirky
Meals:Continental breakfast and evening meals.
Prices from:Please call.
Departs:Saturdays from 08 May 2010 to 16 Oct 2010
  JFMAMJJASOND
Good for:Wine tasing Art and history Local culture Choices for children
Cycling in Italy: Heart of Venetia Cycling


Cycling holiday, Italy
Secrets of Sicily Cycling
Location:Sicily, Italy.
Holiday type:Independent cycling, hotel-to-hotel.
Managed by Headwater appointed agent.
Activity level: 2 bikes
Duration:9 days (8 nights)
Hotels:A mix of luxury/stylish, mid range/good value
Meals:Continental breakfast and all evening meals.
Prices from:Please call.
Departs:Selected Saturdays from 03 Apr 2010 to 16 Oct 2010
  JFMAMJJASOND
Good for:Swimming opportunities Art and history Fauna and flora Bird watching Local culture
Cycling in Italy: Secrets of Sicily Cycling


Cycling holiday, Italy
Secrets of San Gimignano Cycling
Location:Chianti, Italy.
Holiday type:Independent cycling, hotel-to-hotel.
Managed locally by Headwater employed rep.
Activity level:Upper 2 bikes
Duration:9 days (8 nights)
Hotels:Luxury/stylish
Meals:Continental breakfast and all evening meals.
Prices from:Please call.
Departs:Every two days from 30 Nov 1999 to 14 Oct 2010
  JFMAMJJASOND
Good for:Gastronomic meals Wine tasing Swimming opportunities Art and history Fauna and flora Local culture
Cycling in Italy: Secrets of San Gimignano Cycling


Cycling holiday, Italy
Gastronomic Barolo Cycling
Location:Piedmont, Italy.
Holiday type:Independent cycling, hotel-to-hotel.
Managed locally by Headwater employed rep.
Activity level: 2 bikes
Duration:9 days (8 nights)
Hotels:Luxury/stylish
Meals:Continental breakfast and all evening meals.
Prices from:Please call.
Departs:Every two days from 30 Nov 1999 to 14 Oct 2010
  JFMAMJJASOND
Good for:Gastronomic meals Wine tasing Swimming opportunities Art and history Local culture
Cycling in Italy: Gastronomic Barolo Cycling


Cycling holiday, Italy
Contrasts of Puglia Cycling
Location:Puglia, Italy.
Holiday type:Independent cycling, hotel-to-hotel.
Managed by Headwater appointed agent.
Activity level: 2 bikes
Duration:8 days (7 nights)
Hotels:Mid range/good value
Meals:Continental breakfast and evening meals.
Prices from:Please call.
Departs:Selected Saturdays from 03 Apr 2010 to 16 Oct 2010
  JFMAMJJASOND
Good for:Wine tasing Swimming opportunities Art and history Local culture
Cycling in Italy: Contrasts of Puglia Cycling


Cycling holiday, Italy
Aspects of Assisi Cycling
Location:Umbria, Italy.
Holiday type:Independent cycling, hotel-to-hotel.
Managed locally by Headwater employed rep.
Activity level: 2 bikes
Duration:9 days (8 nights)
Hotels:Mid range/good value
Meals:Continental breakfast and evening meals.
Prices from:Please call.
Departs:Every two days from 03 May 2010 to 14 Oct 2010
  JFMAMJJASOND
Good for:Wine tasing Swimming opportunities Art and history Local culture Choices for children
Cycling in Italy: Aspects of Assisi Cycling


Cycling holiday, Italy
Villas and Vineyards Cycling
Location:Venetia, Italy.
Holiday type:Independent cycling, hotel-to-hotel.
Managed locally by Headwater employed rep.
Activity level: 1 bike
Duration:9 days (8 nights)
Hotels:A mix of mid range/good value, friendly/quirky
Meals:Continental breakfast and evening meals.
Prices from:Please call.
Departs:Every two days from 05 May 2010 to 16 Oct 2010
  JFMAMJJASOND
Good for:Wine tasing Art and history Local culture Choices for children
Cycling in Italy: Villas and Vineyards Cycling





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?

More about our cycling holidays...

Cycling holidays in Europe & The Med
Watch our cycling video
How our cycling holidays work
Maps, notes and finding your way
Our bike rating system explained
Browse our range of cycling holidays

Perfect cycling holidays for...

Families with teenagers
Families with under 12's
Solo travellers
Foodies
Wine lovers
Nature lovers & botanists
Bird watchers
Fine arts & historic sites
Local culture & tradition
Last minute departures

Cycling holiday destinations...

Cycling holidays in Austria
Cycling holidays in Britain
Cycling in Cyprus
Cycling holidays in the Czech Republic
Cycling holidays in France
Cycling holiday in Germany
Cycling in Gozo
Cycling holidays in Italy
Cycling in Portugal
Cycling holidays in Spain
Cycling in Switzerland

Other cycling holiday choices...

Short break 'taster' cycling holidays
Value 'lite' cycling holidays
Extended cycling tours

"Thank you for a great holiday. We hadn't booked with Headwater before, or even done a cycling holiday - but we definately will again!"

Mrs Milner, Congleton

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