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Cycling holidays in Italy

Listed below are the holidays that match your search criteria, to view any of the holidays shown simply click on the 'View holiday' button.
To refine your search use the panel above to select the activity type, country, departure months, etc. You can make multiple selections in each of the drop-down categories, or clear your selections by clicking the appropriate 'X' button.


Puglia - Cycling the Heel of Italy
Italy: Puglia

Puglia - Cycling the Heel of Italy

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 US$1999per person, tour only

  • 4 Reviews
  • All accommodation
  • All breakfasts
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Bolzano, Verona & Venice Ride
Italy: The Dolomites

Bolzano, Verona & Venice Ride

Spectacular riding from the stunning Dolomites to Venice. Starting from Bolzano, the capital of the South Tyrol, you'll follow gentle riverside tracks through fragrant orchards and vineyards to reach Lake Garda. Continue the ride through the beautiful cities of Verona, Padova and finally exploring the canals and waterways of Venice.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2049per person, tour only
  • All accommodation
  • All breakfasts
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Heart of Veneto Cycling
Italy: Veneto

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 US$2049per person, tour only

  • 55 Reviews
  • All accommodation
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Venetian Villas and Vineyards Cycling
Italy: Veneto

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 US$2349per person, tour only

  • 43 Reviews
  • All accommodation
  • All continental breakfasts and 6 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Secrets of Sicily Cycling
Italy: Sicily

Secrets of Sicily Cycling

Explore the undiscovered western coast of Sicily by bike to find pristine nature reserves, ancient monuments and Baroque towns. Highlights include Segetsa amphitheatre and Selinunte Archeaological Park.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2549per person, tour only
  • All accommodation
  • All breakfasts and 1 evening meal
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
A Taste of Tuscany Cycling
Italy: Tuscany

A Taste of Tuscany Cycling

This single-centre cycling holiday introduces you to quintessential Tuscany; it has all the ingredients to create a wonderful lasting impression of this rightly famous region: the landscapes, the food, the people and, of course, perfect cycling routes.This is not just a cycling holiday it is an immersion into local Tuscan life.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2699per person, tour only

  • 9 Reviews
  • All accommodation
  • All buffet breakfasts and 4-course evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Secrets of San Gimignano Cycling
Italy: Tuscany

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 US$2949per person, tour only

  • 46 Reviews
  • All accommodation
  • All continental breakfasts and 6 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
From the Dolomites to Lake Garda Cycling
Italy: The Dolomites

From the Dolomites to Lake Garda Cycling

Discover a unique fusion of German and Italian landscapes and architecture as you cycle through relaxed waterfront towns, cosmopolitan cities and traditional pastel-painted Alpines villages to Riva, 'Pearl of Lake Garda'.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3249per person, tour only

  • 27 Reviews
  • All accommodation
  • All buffet breakfasts
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling through Baroque Sicily
Italy: Sicily

Cycling through Baroque Sicily

This eight-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
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3299per person, tour only

  • 10 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Julian Alps to the Adriatic Cycling
Slovenia / Italy

Julian Alps to the Adriatic Cycling

Our 10 night holiday takes you from the turquoise waters of Lake Bled, nestled below Slovenia's jagged Julian Alps, along the Alpe Adria Trail, passing into Italy. Wind down through the mountains to the island of Grado on the Adriatic coast. On route pass through the historic towns of Venzone, Udine and Palmanova.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3849per person, tour only

  • 73 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Wine Trails of Umbria
Italy: 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 medieval 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 US$2579per person, tour only

  • 57 Reviews
  • All accommodation
  • All breakfasts and 6 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Contrasts of Puglia Cycling
Italy: Puglia

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 US$2699per person, tour only

  • 108 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Matera to Monopoli Cycling
Italy: Puglia

Matera to Monopoli Cycling

Start at Matera, one of the oldest inhabited cities in the world and cycle through the Alta Murgia National Park, the largest natural park in Italy. Reach the Adriatic coastline at Trani, known as the 'Pearl of Puglia' and continue your ride, south, along the coast to Bari and your final destination, Monopoli.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2849per person, tour only
  • All accommodation
  • All breakfasts and 1 evening meal
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Gastronomic Barolo Cycling
Italy: Piedmont

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 US$3649per person, tour only

  • 58 Reviews
  • All accommodation
  • All buffet breakfasts and 4 gastronomic evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Medieval Umbrian Cycling
Italy: Umbria

Medieval 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

  • 14 Reviews
  • All accommodation
  • Continental breakfast and 6 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling in Tuscany: Pisa to Florence
Italy: Tuscany

Cycling in Tuscany: Pisa to Florence

Cycle from the iconic leaning tower of Pisa to the Ponte Vecchio in Florence, passing through beautiful Tuscan landscape that inspired artists and composers such as Leonardo da Vinci and Puccini. The gentle cycling is mainly along riverside paths and quiet roads, and there are the opportunities to lengthen the rides, or take the train at some stages to spend extra time at your destinations.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2049per person, tour only
  • All accommodation
  • All breakfasts
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Wine Villages of Piedmont
Italy: Piedmont

Cycling the Wine Villages of Piedmont

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 US$2949per person, tour only
  • All accommodation
  • All buffet breakfasts
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Classic Chianti Cycling
Italy: Tuscany

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 US$3349per person, tour only

  • 25 Reviews
  • All accommodation
  • All buffet breakfasts and 6 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Highlights of Puglia Cycling
Italy: Puglia

Highlights 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, whitewashed Ostuni and beautiful Baroque Lecce.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3799per person, tour only
  • All accommodation
  • All continental breakfasts and 3 evening meals included
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Landscapes of Matera and Puglia Cycling
Italy: Puglia

Landscapes of Matera and Puglia Cycling

Start at Matera, one of the oldest inhabited cities in the world and a UNESCO World Heritage site and cycle through the Alta Murgia National Park. Follow the Adriatic coastline between Trani and Bari before heading inland through unspoilt villages and gently rolling hills. Discover Alberobello, with its trulli houses, and the white village of Ostuni as you wind your way back towards the sea.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration14 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$4449per person, tour only
  • All accommodation
  • All breakfasts and 3 evening meals
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Italian and Swiss Lakes
Italy / Switzerland: Piedmont

Cycling the Italian and Swiss Lakes

Cycle around four iconic lakes in two countries - Italy and Switzerland. Visit Lake Orta, Lake Como, Lake Maggiore and Lake Lugano.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2779per person, tour only
  • All breakfast, 2 lunches and 1 dinner included
  • All accommodation (see below)
  • All transport and listed activities
  • Tour leader throughout
  • Flights from London (if booking incl. flights)
  • Local bike hire

    Cycling holidays in Italy

    Overall customer rating, based on 535 reviews