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.


Cycling from the Dolomites to Venice
Italy: The Dolomites

Cycling from the Dolomites to Venice

From the northeastern Dolomites, cycle through the Alta Val Pusteria below the famous Drei Zinnen, through the valley of the ice cream makers and across the plains to reach Venice.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07DL
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2045per person, tour only

  • 2 Reviews
  • All accommodation
  • All buffet breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Heel of Italy - Alberobello to Lecce
Italy: Puglia

Cycling the Heel of Italy - Alberobello to Lecce

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 codeC07PI
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2255per person, tour only

  • 30 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
The Wine Trails of Umbria Cycling
Italy: Umbria

The Wine Trails of Umbria Cycling

This trip combines scenic pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages. Highlights include panoramic Montefalco, picture-postcard Spello and ancient Assisi.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07UR
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2375per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Brenner Pass to Venice Cycling
Italy: Trentino

Brenner Pass to Venice Cycling

Taking you from the stunning Dolomites to Venice. The cycle route starts at the Brenner Pass, on the border with Austria and you'll follow gentle riverside tracks through fragrant orchards and vineyards. Enjoy a ferry ride across Lake Garda and continue through the beautiful cities of Verona, Padova to the canals and waterways of Venice.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC09VE
  • Holiday typeSelf-guided cycling
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2780per person, tour only

  • 3 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Heel of Italy - Matera to Lecce
Italy: The Bay of Naples

Cycling the Heel of Italy - Matera to Lecce

This 11 night cycling holiday starts in UNESCO Matera, in the Basilicata region and moves on to Puglia. Discover unspoilt villages and gently rolling hills, sandy beaches and interesting towns. Highlights include whitewashed Ostuni and Baroque Lecce.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC11PI
  • Holiday typeSelf-guided cycling
  • Duration11 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3185per person, tour only

  • 5 Reviews
  • All accommodation
  • All breakfasts and 2 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
E-bike Cycling on the Costa Smeralda
Italy: Sardinia

E-bike Cycling on the Costa Smeralda

Let the e-bike do the hard work for you on this wonderful cycling trip discovering the highlights and lesser known inner heartlands of Sardinia's renowned Costa Smeralda. Have lunch in glamorous Porto Cervo, pedal around the stunning island of La Maddalena and admire the pristine white beaches lapped by those famous emerald waters.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07SM
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2720per person, tour only

  • 3 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Heart of Veneto Cycling
Italy: Veneto

Heart of Veneto Cycling

The 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 codeC07VN
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1970per person, tour only

  • 69 Reviews
  • All accommodation
  • All continental breakfasts and evening meals
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Bolzano, Verona & Venice Ride
Italy: Veneto

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. Ride through the beautiful cities of Verona, Padova and finally exploring the canals and waterways of Venice.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07VE
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2150per person, tour only

  • 14 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Route notes 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 Segesta's amphitheatre and Selinunte Archeaological Park.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07MR
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2360per person, tour only

  • 20 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • 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 codeC08VN
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2540per person, tour only

  • 54 Reviews
  • All accommodation
  • All continental breakfasts and 6 evening meals
  • Bike hire included
  • 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

Introducing you to quintessential Tuscany, this cycling holiday 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 codeC07ST
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2750per person, tour only

  • 24 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Secrets of San Gimignano Cycling
Italy: Chianti

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 codeC08TY
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3185per person, tour only

  • 55 Reviews
  • All accommodation
  • All continental breakfasts and 5 evening meals
  • Bike hire included
  • 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 codeC08BS
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3200per person, tour only

  • 18 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • Bike hire included
  • 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 codeC10SV
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$4070per person, tour only

  • 99 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals included
  • Bike hire included
  • 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 codeC07PU
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2795per person, tour only

  • 120 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • Bike hire included
  • 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 codeC08PD
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3635per person, tour only

  • 80 Reviews
  • All accommodation
  • All buffet breakfasts and 4 gastronomic evening meals
  • Bike hire included
  • 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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07PF
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2135per person, tour only

  • 5 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Emilia Romagna – Bologna to Parma Cycling
Italy: The Bay of Naples

Emilia Romagna – Bologna to Parma Cycling

Discover the flavours and art cities of Emilia Romagna on this tasty tour pedalling from Bologna to Parma.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07EM
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2600per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Undiscovered Sardinia Cycling
Italy: Sardinia

Undiscovered Sardinia Cycling

Superb cycling discovering the south west of Sardinia, with its glittering turquoise seas and pure white sand beaches. The trip includes island hopping to St Antioco and St Pietro, visiting the archaeological site of Nora and pedalling along Sardinia's spectacular Costa del Sud.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07SA
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2600per person, tour only

  • 13 Reviews
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Navigation app provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Italian Lakes
Italy: Lombardy

Cycling the Italian Lakes

Journey between seven beautiful Italian Lakes as you explore this colourful and cultural region.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07TL
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2780per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation 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 codeC08PB
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3065per person, tour only

  • 5 Reviews
  • All accommodation
  • All buffet breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Classic Chianti Cycling
Italy: Chianti

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 codeC10TY
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3605per person, tour only

  • 26 Reviews
  • All accommodation
  • All buffet breakfasts and 5 evening meals
  • Bike hire included
  • 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 codeC10PU
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3920per person, tour only

  • 7 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals included
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)

    Cycling holidays in Italy

    Overall customer rating, based on 652 reviews