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Cycling in Italy

There's something very special about Italy, whether you're a first time visitor or seasoned traveller you'll soon fall under its spell. Few countries are as diverse, it offers mountains, sparkling coastlines, ancient history and sumptuous cuisine. Whether you're passing through the great art cities of Tuscany and Umbria, or admiring the rolling hills and ancient forests of Venetia with their amazing array of beautiful wild flowers, or enjoying the dramatic coastlines of the Island of Sicily you can really get 'under the skin' of the real country on a Headwater cycling holiday in Italy.

We have an array of journeys for all abilities to enjoy - 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? In-between days are a great opportunity for even more local exploring, using our detailed maps and route notes as your guide.

View 10 holidays below


Contrasts of Puglia Cycling

Contrasts of Puglia Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From Call usper person, tour only

  • 77 Reviews
  • All continental breakfasts and 3 evening meals included
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Secrets of San Gimignano Cycling

Secrets of San Gimignano Cycling

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From Call usper person, tour only

  • 37 Reviews
  • All continental breakfasts and evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Cycling the Wine Trails of Umbria

Cycling the Wine Trails of Umbria

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From Call usper person, tour only

  • 43 Reviews
  • All breakfasts and 6 evening meals included
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Mediaeval Umbrian Cycling

Mediaeval Umbrian Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From Call usper person, tour only

  • 13 Reviews
  • Continental breakfast and 6 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Heart of Veneto Cycling

Heart of Veneto Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £839per person, tour only

  • 58 Reviews
  • All continental breakfasts and evening meals included
  • High quality bikes provided
  • GPS route navigation provided
From the Dolomites to Lake Garda Cycling

From the Dolomites to Lake Garda Cycling

Offering a stunning yet dominant backdrop to the region is the UNESCO Dolomites, their jagged rock walls overlook the deep green meadows, acres of fragrant apple orchards and, further south, the lush vineyards of Trentino below.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £959per person, tour only
  • All buffet breakfasts included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Venetian Villas and Vineyards Cycling

Venetian Villas and Vineyards Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £999per person, tour only

  • 36 Reviews
  • All continental breakfasts and evening meals included
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
Classic Chianti Cycling

Classic Chianti Cycling

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1549per person, tour only

  • 21 Reviews
  • All buffet breakfasts and 8 evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Gastronomic Barolo Cycling

Gastronomic Barolo Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1579per person, tour only

  • 49 Reviews
  • All buffet breakfasts and gastronomic evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
A Taste of Sicily Cycling

A Taste of Sicily Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1799per person, tour only

  • 9 Reviews
  • All continental breakfasts and 6 evening meals
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels