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Cycling holidays with GPS route navigation

The Headwater Navigation App provides our comprehensively researched and carefully checked routes in an easy to use and convenient format, like a car satnav, with easy-to-follow turn-by-turn instructions all along your route.

We offer GPS route navigation on many of our cycling holidays so even if you have no map reading skills - you won't get lost with Headwater!

Find out about the benefits of GPS route navigation to see how our relaxed cycling holidays are now even better!


Cycling from Copenhagen
Denmark

Cycling from Copenhagen

Enjoy daily rides heading out from capital of Denmark, Copenhagen to discover Viking history and relax at sandy beaches.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC04DC
  • Holiday typeSelf-guided cycling
  • Duration4 nights, single centre
  • Activity level
  • Excellent for
  • From US$1850per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • Breakfast
  • Bike hire included
  • Headwater navigation provided
  • 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$2120per person, tour only

  • 27 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 7-night holiday 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$2300per 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 in the Peloponnese
Greece

Cycling in the Peloponnese

Embark on an exhilarating cycling tour through the heart of Greece's Peloponnese region. Pedal diverse terrains - mountains, coast, ancient cities, and charming seaside towns. Explore historical treasures such as Mycenae and Epidaurus, pausing for authentic Greek delights. Each night, relax in meticulously selected hotels, merging luxury with Peloponnesian tranquillity.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07GP
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2630per person, tour only

  • 5 Reviews
  • All accommodation
  • All continental breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Heel of Italy - Matera to Lecce
Italy: Puglia

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$3200per 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)
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 codeC07VN
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1855per 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)
Cycling in The Real Algarve
Portugal: The Algarve

Cycling in The Real Algarve

Discover a land that time forgot as you explore the unspoilt wild coastlines, pretty white villages and deserted cycling routes of the Algarve. The area is a birdwatchers paradise, with endemic and migratory species passing through from Africa and Northern Europe.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06AV
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2300per person, tour only

  • 54 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)
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)
Cotes du Ventoux Cycling
France: Provence

Cotes du Ventoux Cycling

The Vaucluse is characterised by several things but none perhaps as much as the vineyards which cover the patchwork landscape and the ever present shape of Mt Ventoux, 'the Giant of Provence', silent and ever watchful on the horizon. This 6 night cycle takes you around the eastern side of the Vaucluse, where you will have ample opportunities to taste the local produce as you venture right up to the foot of the mountain.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06PV
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2425per person, tour only

  • 36 Reviews
  • All accommodation
  • All continental breakfasts and 4 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

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 codeC07ST
  • Holiday typeSelf-guided cycling
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2750per person, tour only

  • 22 Reviews
  • All accommodation
  • All breakfasts and 4-course evening meals
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Landscapes of the Luberon Cycling
France: Provence

Landscapes of the Luberon Cycling

The picturesque, perched villages of Provence offer stirring images along with a history which, in some places, stretches back over a thousand years. On this 8 night holiday you'll discover vineyards, olive groves, monasteries, chateaux and caves along with the region's famous Ochre Trail and, of course, the lavender which scents the summer air.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08PL
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3035per person, tour only

  • 21 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • 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$2985per 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)
County Kerry Cycling
Ireland

County Kerry Cycling

Cycle a quieter mix of inland and coastal routes close to the famous Ring of Kerry. Experience the 'real' Ireland on the Iveragh Peninsula; it's mystical, beautiful and grand, and you'll certainly soak up the charming Irish welcome en route, with live music and delicious seafood too.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06KE
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2150per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Coastal Croatia  - Pula to Porec Cycling
Croatia

Coastal Croatia - Pula to Porec Cycling

The Istrian peninsula just south of Trieste is a superb backdrop for a cycling holiday. Swim in the clear blue waters of the Adriatic and stay in gorgeous Italianate harbour towns. Great food, interesting routes, masses of history and electrifying sunsets make discovering this coastline particularly memorable.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07IS
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2300per person, tour only

  • 82 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Contrasts of Catalunya Cycling
Spain: Catalonia

Contrasts of Catalunya Cycling

Packed with contrast and variety, this easy 6-night cycling tour takes in the unspoilt Catalan coast, passing through olive groves, peach orchards and stunningly beautiful, pretty coloured villages. All the hotels have pools, and 2 nights are spent in a luxury 14th century castle.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06CN
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2375per person, tour only

  • 51 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)
Cycling in Andalucia: Seville to Cadiz
Spain: Andalucia

Cycling in Andalucia: Seville to Cadiz

Discover one of Spain's most iconic areas by bike. From the capital city of Andalucia, Seville, cycle through small towns to reach your final destination, the ancient city of Cadiz. You'll follow country lanes, ride alongside rivers and through Mediterranean woodland and agricultural land taking in some of the highlights of the region including Jerez, home of flamenco and sherry and Arcos de la Frontera, one of Andalucia's most dramatically positioned white villages.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06AD
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$200per person, tour only

  • 12 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Cycling in Mallorca: Coast to Coast
Spain: Mallorca

Cycling in Mallorca: Coast to Coast

Easy cycling across Mallorca, taking in coastal trails and beautiful inland routes

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07MA
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2540per person, tour only

  • 14 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Contrasts of Norfolk Cycling
United Kingdom: Norfolk

Contrasts of Norfolk Cycling

This self-guided 7-night cycling tour takes in some of the best Norfolk has to offer, cycling on coastal routes and quiet country lanes between charming villages and to places of interest including Sandringham and Holkham Hall. Enjoy the natural surroundings with the possibility of bird spotting and seal spotting.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07NO
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2630per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
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)
Lake Constance Cycling
Austria / Germany / Switzerland: Lake Constance

Lake Constance Cycling

Looking for a holiday where relaxing cycling effortlessly intertwines with nature, culture, delightful cuisine, refreshing swims, and historic sights? Your dream trip is here! Our Lake Constance Cycling trip guides you through picturesque towns, vineyards, and captivating historic sites in Germany, Switzerland, and Austria. Indulge in local treats, dip into turquoise waters, and embrace vibrant events.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC10LC
  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2960per person, tour only

  • 80 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Dordogne Valleys & Villages Cycling
France: The Dordogne

Dordogne Valleys & Villages Cycling

Wonderful gastronomic meals, world-famous wines, fabulous historic sites and postcard-pretty villages are just a few of the highlights of this popular 8-night cycling tour. You're usually close to the rivers too, so lots of swimming, plus all hotels have pools.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08DO
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2990per person, tour only

  • 39 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)
Porto Coastal Cycling
Portugal: Mainland Portugal

Porto Coastal Cycling

Varied beach-front cycling along some of the most spectacular stretches of coast we've ever seen! Starting in wine capital, Porto, your route heads south beach and bay-hopping to Aveiro, Portugal's Venice before finishing beside the beach at Praia de Mira.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07OP
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3050per person, tour only

  • 57 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)
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 Lake Garda with e-bike
Italy: Veneto

Cycling Lake Garda with e-bike

Spend 6 nights on Lake Garda, the playground of cycling! Your unique hotel has been transformed from an old rail station, close to the waters edge.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06LG
  • Holiday typeSelf-guided cycling
  • Duration6 nights, single centre
  • Activity level
  • Excellent for
  • From US$1580per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Contrasts of Catalunya Cycling - Short Break
Spain: Catalonia

Contrasts of Catalunya Cycling - Short Break

Packed with contrast and variety, this easy 4-night cycling tour takes in the unspoilt Catalan coast, passing through olive groves, peach orchards and stunningly beautiful, pretty coloured villages. All the hotels have pools and 1 night is spent in a luxury 14th century castle.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC04CN
  • Holiday typeSelf-guided cycling
  • Duration4 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2000per person, tour only

  • 4 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)
Cycling from Stockholm
Sweden

Cycling from Stockholm

A 5 night single centre holiday based in Stockholm with daily cycle routes around the city and into the archipelago. A fabulous region to explore by bike with many cultural highlights including UNESCO Drottningholm Palace along with the natural highlights of the islands.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC05SI
  • Holiday typeSelf-guided cycling
  • Duration5 nights, single centre
  • Activity level
  • Excellent for
  • From US$1879per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • Breakfast
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Highlights of Norfolk Cycling
United Kingdom: Norfolk

Highlights of Norfolk Cycling

Discover some of the highlights of North Norfolk. Cycle on quiet country lanes from village to village with many places of interest along the way - visit Sandringham and Houghton Hall. Go bird spotting at RSPB Snettisham and seal spotting at Blakeney.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC05NO
  • Holiday typeSelf-guided cycling
  • Duration5 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1935per person, tour only

  • 10 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Hilltop Villages of Provence Cycling - Short Break
France: Provence

Hilltop Villages of Provence Cycling - Short Break

Provence is a place whose natural light and landscapes have served as inspiration to such iconic figures as Van Gogh, Cezanne, Picasso and Dumas (not to mention Peter Mayle!), and this 4 night holiday has been designed to give you a taste of the famous hilltop villages which dot its breath-taking, lavender-scented Luberon region.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC04PL
  • Holiday typeSelf-guided cycling
  • Duration4 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2090per person, tour only

  • 6 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)
Azores Cycling
Portugal: The Azores

Azores Cycling

In Terceira Island, explore the stunning coastline and the luxurious green pastures. Enjoy landscapes of dramatic lava coastline and natural pools, visit a volcano pit, a UNESCO World Heritage Town, and ride along lush green sceneries.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06AZ
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2150per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Highlights of Lake Constance by bike
Austria / Germany / Switzerland: Lake Constance

Highlights of Lake Constance by bike

Explore Lake Constance by bike on gentle cycling trails, stopping for lunches at waterfront restaurants and discovering some of the cultural and historic highlights of this region, staying in Austria, Switzerland and Germany.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07LC
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2180per person, tour only

  • 19 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Unspoilt Ring of Kerry Cycling
Ireland

Unspoilt Ring of Kerry Cycling

Cycle a quieter mix of inland and coastal routes close to the famous Ring of Kerry. Experience the 'real' Ireland on the Iveragh Peninsula; it's mystical, beautiful and grand, and you'll certainly soak up the charming Irish welcome en route, with live music and delicious seafood too.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07KE
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2255per person, tour only
  • All accommodation
  • All breakfasts and 1 evening meal
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Cycling through the Unspoilt Costa Blanca
Spain: Andalucia

Cycling through the Unspoilt Costa Blanca

A 6 night cycling holiday exploring the unspoilt inland area of Alicante discovering pretty Spanish villages and the Mariola National Park before enjoying two nights by the beach in the charming towns of Denia and Javea.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06CB
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2360per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Coast of Eastern Crete
Greece

Cycling the Coast of Eastern Crete

Embark on a scenic cycling tour through Eastern Crete, exploring picturesque villages and golden beaches. Indulge in local delights, from signature cheeses to Raki, all while pedalling along the stunning coastline. Stay in charming family-run accommodations and witness the island’s rich biodiversity. A perfect blend of nature, culture, and gastronomy makes this cycling holiday unforgettable.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07CT
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2390per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling Valencia and the Orange Blossom Coast
Spain: Valencia

Cycling Valencia and the Orange Blossom Coast

A 7 night holiday in the Valencia region with 2 nights in the city of Valencia exploring off the beaten track inland valleys and gentle coastal cycling past secluded beaches and un-spoilt Nature Reserves and finishing in the charming town of Peniscola.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07VA
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2405per person, tour only

  • 7 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling the Algarve's Rota Vicentina
Portugal: The Algarve

Cycling the Algarve's Rota Vicentina

Follow the Rota Vicentina cycling path from Setubal to the Cape Sao Vicente, along rugged coastline with amazing views over cliffs and large sandy beaches.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07RV
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2420per person, tour only

  • 6 Reviews
  • All accommodation
  • All Breakfasts included
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling Stockholm's Archipelago
Sweden

Cycling Stockholm's Archipelago

Experience the Scandinavian flair of Stockholm and its beautiful archipelago. There are more than 30.000 islands but you'll visit just a few! Following waterfront and forested trails you'll discover small towns and nature reserves before returning to the capital, Stockholm.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06SI
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2450per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • Breakfast
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Hilltop Villages of Provence Cycling
France: Provence

Hilltop Villages of Provence Cycling

Provence is a place whose natural light and landscapes have served as inspiration to such iconic figures as Van Gogh, Cezanne, Picasso and Dumas (not to mention Peter Mayle!), and this 6 night holiday has been designed to give you a taste of the famous hilltop villages which dot its breath-taking, lavender-scented Luberon region.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06PL
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2525per person, tour only

  • 16 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)
Classic Catalan Cycling
Spain: Catalonia

Classic Catalan Cycling

This 8-night holiday explores the wonderfully undiscovered Catalan countryside, a region of pine-fringed valleys dotted with historic castles, hilltop fortresses, ancient wine villages and beautiful countryside. It's wonderfully quiet cycling too, where you can discover unspoilt Catalonia (Catalunya).

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08CL
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2525per person, tour only

  • 9 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)
Vineyards of La Rioja Cycling
Spain: Rioja

Vineyards of La Rioja Cycling

This 7 night holiday offers peaceful cycling along quiet country lanes and tracks in La Rioja, home of the famous La Rioja Spanish wine. Cycle through the heart of this celebrated wine region amongst the vineyards and past wineries and wine museums and where a glass of wine waits at every turn.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07RI
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2540per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling in Portugal: From the Mountains to the Sea
Portugal: Mainland Portugal

Cycling in Portugal: From the Mountains to the Sea

You cycle through small villages and extensive vineyards, following the River Minho towards the Atlantic Ocean. The scenery is a stunning combination of high mountains, rolling river scenes, historic towns and dramatic coastal landscape.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07MI
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2425per person, tour only

  • 11 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Best of the Cotswolds Cycling
United Kingdom: The Cotswolds

Best of the Cotswolds Cycling

A 6-night self-guided cycling tour on some of the best off the beaten track routes in the Cotswolds, staying in the beautiful and historic villages of Broadway and Bourton-on-the-Water.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06CO
  • Holiday typeSelf-guided cycling
  • Duration6 nights, twin centre
  • Activity level
  • Excellent for
  • From US$2750per person, tour only
  • All accommodation
  • Breakfast daily
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
Cycling in the Douro Valley
Portugal: Mainland Portugal

Cycling in the Douro Valley

Explore the Douro Valley and its historical villages on our 6-night self-guided tour. Starting from the medieval village of Castelo Rodrigo, close to the Spanish border you'll cycle through uniquely terraced vineyards on your way to port wine town of Peso da Regua.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC06DV
  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2750per person, tour only

  • 5 Reviews
  • All accommodation
  • All breakfasts and one evening meal.
  • Bike hire included
  • Headwater navigation 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)
Vineyards of Vaucluse Cycling
France: Provence

Vineyards of Vaucluse Cycling

For wine-lovers, this 8-night tour circles the famous Cotes de Rhone vineyards, and includes 2 nights in Vaison la Romaine - France's most extensive Roman site with 6000-seat theatre, baths, houses and streets. Swimming pools 6 nights out of 8.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08PV
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3005per person, tour only

  • 17 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)
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$2875per 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)
Porto to Coimbra Cycling
Portugal: Mainland Portugal

Porto to Coimbra Cycling

Enjoy cycling from wine capital, Porto, south along the coast and bay-hopping to Aveiro, Portugal's Venice before heading inland and finishing in Coimbra, Portugal's old capital with UNESCO recognised heritage.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC09OP
  • Holiday typeSelf-guided cycling
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3185per person, tour only

  • 50 Reviews
  • All accommodation
  • All continental breakfasts and 4 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Stockholm to Copenhagen Cycling
Sweden / Denmark

Stockholm to Copenhagen Cycling

Cycle between two Nordic capitals, departing from Stockholm and following in part the Kattegat route along Sweden's West Coast. There is a lot to discover, from the UNESCO Drottningholm Palace and Hamlet's Kronborg Castle to the fascinating archipelago of Gothenburg, culminating in Denmark's capital, Copenhagen.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07SD
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3200per person, tour only
  • NEW FOR 2024  
  • All accommodation
  • Breakfast
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Secrets of Slovenia Cycling
Slovenia

Secrets of Slovenia Cycling

Our 7 night holiday starts at picture postcard Lake Bled in the Julian Alps, follows the emerald Soča River, takes you through the 'Tuscany' of Slovenia and across the mysterious world of the Karst to the medieval town of Piran on the Adriatic coast.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07SN
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3425per person, tour only

  • 7 Reviews
  • All accommodation
  • All continental breakfasts and 1 evening meal
  • 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$3380per 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)
Mountain Biking the Valais Matterhorn Region
Switzerland: Valais

Mountain Biking the Valais Matterhorn Region

This mountain biking trip takes you across a vast landscape of mountains and valleys, to vineyards and glaciers, all the while accompanied by the crisp Swiss air and far-reaching vistas. You’ll stay in beautiful-chalet style accommodations, nestled amongst the Valais Alps.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07VL
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3749per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Cycling Maine's Coast & National Park
USA: Maine

Cycling Maine's Coast & National Park

Cycle the very best of Maine’s diverse coastline, from the quiet beauty of Pemaquid Point and up to the shores of Penobscot Bay, you’ll end your New England adventure with a victory lap of Acadia National Park. Luxury accommodation, exceptional local food, and scenic trails await.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC07MN
  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$4920per person, tour only
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Walking and E-biking in the Swiss Alps
Switzerland: The Bernese Oberland

Walking and E-biking in the Swiss Alps

This 7 night holiday explore the peaks of the Bernese Oberland of Switzerland on foot and by e-bike to help you combat those hills. Stay at the beautiful Alfa Soleil with excellent cuisine in a chocolate box perfect setting of Kandersteg.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeM07AF
  • Holiday typeMulti activity holiday
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2435per person, tour only

  • 13 Reviews
  • All accommodation
  • All breakfasts, picnic or light restaurant lunches and 4 course dinners included each day
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Austrian Lakes Activities
Austria: Salzburg

Austrian Lakes Activities

Stay in a luxury 4-star hotel with a top-of-the-range wellness centre and choose from a host of activities: walking, cycling (route notes for both provided), water sports, boat trips, and ice caves. Complimentary Headwater bikes are included for the duration of your stay.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeM07SZ
  • Holiday typeMulti activity holiday
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$2540per person, tour only

  • 67 Reviews
  • All accommodation
  • All continental breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Catalonia Activities
Spain: Catalonia

Catalonia Activities

Combine a stay at the beach with your choice of gentle walking and cycling routes for an active family holiday. You stay in the fishing village of Calella de Palafrugell, where the rocky coastline has small coves to explore.

We provide a range of fully researched, self-guided walking and cycling routes, typically at activity level 1, making this an ideal family activity holiday with children. Throughout your stay, a complimentary Headwater bike for your exclusive use is provided to give you total flexibility.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeM07CL
  • Holiday typeMulti activity holiday
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From US$1910per person, tour only

  • 12 Reviews
  • All accommodation
  • All breakfasts
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)
Cycling the Camino de Santiago
Spain: Galicia

Cycling the Camino de Santiago

The Spanish Camino de Santiago is one of THE most ancient pilgrims routes in the world. Since the 9th century, the French Way has led thousands of pilgrims on an 800km journey across northern Spain, winding from the Pyrenees across the wheat fields of old Castile to pass through to Leon. Your journey begins in Leon. Leon is the seat of the Spanish Kings and is full of soaring cathedrals and hushed convents. The route then builds through the Galician countryside to a spectacular finale at Santiago de Compostela's majestic Baroque cathedral, the last resting place of St James the apostle.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeC08CS
  • Holiday typePilgrimage
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2945per person, tour only

  • 4 Reviews
  • All accommodation
  • 8 breakfasts and 4 evening meals
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Dordogne Activities
France: The Dordogne

Dordogne Activities

Combine three of our exciting holidays to experience the ultimate activity holiday in the Dordogne. Two days of safe, leisurely canoeing with a choice of easy walking or cycling on the other days.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday codeM08DO
  • Holiday typeMulti activity holiday
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3200per person, tour only

  • 29 Reviews
  • All accommodation
  • All continental breakfasts and 5 evening meals
  • Bike hire included
  • Headwater navigation provided
  • Flights from London (if booking incl. flights)