Winner Best Activity Holidays - Italia Magazine 2015-16Cycling in Italy

Here is our range of cycling holidays in Italy

You move on between hotels, 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 Venetian 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.

Heart of Veneto Cycling

albara and its terrace

From $1256 per person

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This single centre cycling holiday is a perfect choice for people wanting a genuine grass-roots Italian experience. You'll stay on a family-run farm, in the heart of the Venetian countryside, with private pool and vineyards. Venice, Verona and Padua are all possible day trips.

Departures:
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  • 7 nights, single centre
  • All continental breakfasts and evening meals included
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Especailly good for solo travellers.

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Venetian Villas and Vineyards Cycling

Church building in Venetia, Italy.

From $1525 per person

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Wonderfully easy hotel-to-hotel cycling route exploring the pretty villages, villas and castles of the Venetian countryside. Lots of historic interest and great regional cooking! A day trip to Venice is a 'must' with Padua and Vicenza also within reach.

Departures:
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  • 8 nights, hotel-to-hotel
  • All continental breakfasts and evening meals included
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Eco-friendly holidays.
  • Especailly good for solo travellers.
  • Perfect for couples.

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Secrets of Sicily Cycling

Scopello coast, Sicily

From $1732 per person

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This 7-night cycling route explores Sicily's unspoilt western coast, a sun-drenched landscape of golden bays, azure waters, swaying vines and tiny farming hamlets unchanged over the years. Lots of historic interest too: mediaeval Erice, ancient Segesta and sea-facing Marsala.

Departures:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts and evening meals included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.
  • Option to hire electric bikes.

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Contrasts of Puglia Cycling

Cycling along the Puglian coast

From $1729 per person

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Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello and whitewashed Ostuni.

Departures:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts and 3 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Option to hire electric bikes.

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Secrets of San Gimignano Cycling

Poppy field with San Ginignano town

From $1868 per person

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This 8-night cycling holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in high quality hotels, enjoy superb meals and relax by panoramic pools - views extend as far as Corsica on a clear day!

Departures:
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  • 8 nights, hotel-to-hotel
  • All continental breakfast and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Perfect for couples.

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Italian Alps to Lake Garda Cycling

Torbole, Trentino

From $1851 per person

Soak up the natural beauty of northern Italy's timeless mountain scenery in the provinces of South Tyrol and Trentino, as you ride from the alpine pass at Resia to the shores of Lake Garda. The cycling is mostly along riverside cycle paths, through orchards and vineyards, with a backdrop of lakes and mountains, and you'll discover the historic cities of Merano, Bolzano and Trento along the way.

Departures:
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  • 9 nights, hotel-to-hotel
  • All buffet breakfasts and 3 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Beautiful lakes and rivers.

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Cycling in Emilia Romagna

Fantastic art cities

From $2089 per person

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One of the flattest cycling routes in our programme, this is a great holiday for older couples or first timers. Highlights include gorgeous Comacchio, historic Ravenna, the university town of Bologna, with its leaning towers, and the splendid Renaissance city of Ferrara.

Departures:
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  • 8 nights, hotel-to-hotel
  • All Continental breakfast and 6 evening meals included
  • Holidays with gastronomic meals.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Option to hire electric bikes.

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Classic Chianti Cycling

San Gimignano city  from Tuscan countryside.

From $2378 per person

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This 10-night cycling tour combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in high quality hotels, enjoy superb meals and relax by panoramic pools with views that extend as far as Corsica on a clear day!

Departures:
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  • 10 nights, hotel-to-hotel
  • All buffet breakfasts and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.

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A Taste of Sicily Cycling

Ragusa Ibla

From $2497 per person

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This ten-night, self-guided cycling holiday provides a wonderful introduction to Sicily’s south east, a part of the island renowned for its beautiful, unspoilt coastline, spectacular Baroque architecture and sumptuous regional cuisine.

Departures:
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  • 10 nights, hotel-to-hotel
  • 10 breakfasts and 6 evening meals
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Follow stunning coastal routes.
  • Delightful island holidays.

View holiday

Classic Puglia Cycling

Overlooking Alberobello, Puglia

Please call for details

Firmly tucked away in the South, Puglia is a sun-soaked region of deserted white sand beaches, unspoilt villages and gently rolling hills backing the clear emerald seas of the Adriatic. Highlights include UNESCO Alberobello, whitewashed Ostuni and beautiful Baroque Lecce.

Departures:
J
F
M
A
M
J
J
A
S
O
N
D
  • 10 nights, hotel-to-hotel
  • All continental breakfasts and 3 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Option to hire electric bikes.

View holiday

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Headwater's Cycling in Italy 4.5731707317073 328
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  • Relaxed activity holidays since 1985

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