Feefo - Independent reviews
  Contact Us

Request a Brochure | Newsletter

Advanced options

Cycling Holidays 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.


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$2379per person, tour only

  • 93 Reviews
  • All accommodation
  • All continental breakfasts and 3 evening meals
  • High quality bikes provided
  • GPS route 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$2549per person, tour only

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

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 US$2549per person, tour only

  • 24 Reviews
  • All accommodation
  • All buffet breakfasts
  • High quality bikes provided
  • Route notes and maps 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$3099per person, tour only

  • 65 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • High quality bikes provided
  • GPS route 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$3579per person, tour only

  • 56 Reviews
  • All accommodation
  • All buffet breakfasts and gastronomic evening meals
  • High quality bikes provided
  • GPS route 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

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1779per 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 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$1399per 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)
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$1799per 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$1899per person, tour only

  • 55 Reviews
  • All accommodation
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • GPS route 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$2149per person, tour only

  • 39 Reviews
  • All accommodation
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • GPS route 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$2379per person, tour only

  • 5 Reviews
  • All accommodation
  • All buffet breakfasts and 4-course evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • 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 US$2599per person, tour only

  • 14 Reviews
  • All accommodation
  • Continental breakfast and 6 evening meals
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
  • 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$2679per person, tour only

  • 43 Reviews
  • All accommodation
  • All continental breakfasts and evening meals
  • High quality bikes provided
  • GPS route 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$2879per person, tour only

  • 8 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • High quality bikes provided
  • GPS route 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 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
  • GPS route 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$2999per person, tour only

  • 25 Reviews
  • All accommodation
  • All buffet breakfasts and 6 evening meals
  • High quality bikes provided
  • GPS route 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$3179per person, tour only
  • All accommodation
  • All continental breakfasts and 3 evening meals included
  • High quality bikes provided
  • GPS route navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Adriatic: Venice to Porec
Italy: Veneto

Cycling the Adriatic: Venice to Porec

Cycle through three different countries from Italy to Croatia

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1249per person, tour only
  • All breakfasts
  • All accommodation (see accommodation section)
  • All luggage transfers
  • Route notes and maps
  • Local bike hire

    Cycling Holidays Italy

    Overall customer rating, based on 481 reviews

Frequently asked questions

What is the best time of year for cycling in Italy?

We have designed our cycling holidays to be between April and October although it's worth bearing in mind that the further south you go, the hotter you get! For this reason, we don't offer any cycling trips during July and August for our Sicilian holidays. If you'd rather cycle in cooler weather, we'd recommend going North or just choosing a date either side of the peak summer months.

What is included in the price for Italian cycling holidays?

As standard, all our Italian cycling holidays include travel to and from the airport and between the first and last hotel. Once there, luggage is transferred from each hotel, high quality hybrid bikes are provided along with GPS or detailed instructions and maps. All breakfasts are included along with any evening meals detailed in your itinerary.

What abilities are catered for on our cycling holidays in Italy?

We've designed our cycling holidays for all levels of fitness. We've created a grading system based on the difficulty of the routes to help you choose a holiday that you'll be comfortable with. In addition we have marked each trip with an Activity Rating Level on each holiday page and in our brochure so that you'll be fully up to speed with what each trip entails. Some of our holidays contain more than one choice of routes offering an easier alternative to the main route.

Will Headwater arrange travel to and from Italy?

Travel to and from Italy can be included with all packages. Our team will find the mode of travel you'd prefer and book it for you on your behalf. Upgrades to business, club and first class are available on request.

Is customer service available 24/7 in Italy while on holiday?

Our team is on hand around the clock ready to deal with any problems that might arise. Our team in Italy is made up of Headwater-employed reps, local partners and hoteliers - so you'll never be far from someone who can help.