Cycling 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.

Gastronomic Barolo Cycling

mel near vineyards with bike in piedmont

Please call for details

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Superb hotels, world-famous wines and exceptional cuisine are just some of the reasons to choose this 8-night cycling holiday! The cycling takes you through softly rolling hills, sun-drenched hamlets and via the pretty wine towns of Barbaresco and Barolo.

Departures:
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  • 8 nights, hotel-to-hotel
  • Continental breakfast and 8 gastronomic evening meals
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.

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Secrets of San Gimignano Cycling

Poppy field with San Ginignano town

Please call for details

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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
  • Continental breakfast and 6 evening meals
  • 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

Torbole, Trentino

Please call for details

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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  • 8 nights, hotel-to-hotel
  • Buffet breakfasts and 4 evening meals (3 evening meals in August)
  • 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.
  • Good choice for families.
  • Explore the high peaks.
  • Beautiful lakes and rivers.

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Aspects of Assisi Cycling

Leaving Assisi on a bike

Please call for details

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This 8-night holiday combines gentle pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages. Highlights include mediaeval Bevagna, Etruscan Perugia, picture-postcard Spello and ancient Assisi.

Departures:
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  • 8 nights, hotel-to-hotel
  • Continental breakfast and evening meals
  • 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.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Good choice for families.

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Classic Chianti Cycling

San Gimignano city  from Tuscan countryside.

Please call for details

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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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F
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M
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  • 10 nights, hotel-to-hotel
  • Continental breakfast and 6 evening meals
  • 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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Contrasts of Puglia Cycling

Cycling along the Puglian coast

Please call for details

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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
  • Continental breakfast and 3 evening meals
  • 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.

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Cycling in Emilia Romagna

Town hall at Emilia-Romagna

Please call for details

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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
  • Continental breakfast 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.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.
  • Option to hire electric bikes.

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Heart of Venetia Cycling

albara and its terrace

Please call for details

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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
  • Continental breakfast and evening meals
  • 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.
  • Good choice for families.

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Mediaeval Umbrian Cycling

Cycle to Eggi

Please call for details

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This 10-night holiday combines gentle pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages with 4 nights spent in Spoleto with its fantastic architecture and opportunities to visit Rome and Norcia, famed for its cured meats.

Departures:
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M
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  • 10 nights, hotel-to-hotel
  • Continental breakfast and evening meals
  • 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.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Good choice for families.

View holiday

Secrets of Sicily Cycling

Boats and house, Scopello coast, Sicily Island

Please call for details

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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
  • Continental breakfast and all evening meals
  • 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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Venetian Villas and Vineyards Cycling

Church building in Venetia, Italy.

Please call for details

****#

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:
J
F
M
A
M
J
J
A
S
O
N
D
  • 8 nights, hotel-to-hotel
  • Continental breakfast and evening meals
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Good choice for families.

View holiday

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Headwater's Cycling in Italy 3.6241134751773 282
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