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Headwater bestsellers - our most popular cycling holidays

After more than three decades spent searching out the very best hidden gems the world has to offer, we're pleased to say we've uncovered some real winners. These are our most popular cycling holidays - known to please, charm and delight in equal measures. A mix of different destinations, cycling styles and a variety of scenery are all represented amongst these favourites, but what unites them is our passion for these idyllic corners of the world.

Headwater has been helping travellers discover the best of these beautiful regions for years, uncovering local traditions, travelling through the landscapes along the quietest, prettiest routes and meeting the people who call each place home. We'd love to share them with you.


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)
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 2 evening meals included
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
  • Flights from London (if booking incl. flights)
Classic Cotswolds Cycling
United Kingdom: The Cotswolds

Classic Cotswolds Cycling

This self-guided 5-night cycling tour is a fairly easy bike ride through some of the most picturesque villages and some of the best scenery that the Cotswolds has to offer. Visit world-famous and quaint English golden-stone villages including Chipping Campden, Bourton-on-the-Water and the Saxon capital of Winchcombe.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration5 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$1979per person, tour only
  • All accommodation
  • Breakfast daily
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
Cycling along the Danube from Vienna to Budapest
Austria / Slovakia / Hungary: The Danube

Cycling along the Danube from Vienna to Budapest

Enjoy meandering rides along the Danube river and through 3 iconic cities - from Vienna in Austria, through Bratislava in Slovakia and on to Budapest in Hungary. The cycling is mostly along the river through small villages and nature reserves but the real highlights are some of the stunning architecture to be seen in the cities.

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)
Loch Ness and the Highlands Cycling
United Kingdom: Scotland

Loch Ness and the Highlands Cycling

Known for tales of the seldom seen monster, the area around Loch Ness is also famous for having some of the most spectacular natural scenery in the UK. Here numerous other lochs await discovery along with ruined castles, shady forests, tranquil waterways, high viewpoints, hidden waterfalls, a huge variety of wildlife (including many birds of prey and notably golden eagles) and a history that at times seems indiscernible from the area's timeless folklore.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2279per person, tour only
  • All accommodation
  • All breakfasts
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
Contrasts of Norfolk Cycling
United Kingdom

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 typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2379per person, tour only

  • 8 Reviews
  • All accommodation
  • All breakfasts
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
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 typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2449per person, tour only

  • 39 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)
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 typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2449per person, tour only

  • 63 Reviews
  • 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 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 typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2579per person, tour only
  • All accommodation
  • All breakfasts
  • High quality bikes provided
  • 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 typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2649per person, tour only
  • All accommodation
  • All breakfasts
  • 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)
Lake Constance Cycling
Austria / Germany / Switzerland: Lake Constance

Lake Constance Cycling

With over 250km of gentle cycling trails - plus the option to hop on/off the local train (with your bike) - this region is perfect for exploring by bike. You'll visit Baroque churches, Gothic cathedrals, fairytale palaces - and the views are pretty special too!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2779per person, tour only

  • 55 Reviews
  • All accommodation
  • All breakfasts
  • High quality bikes provided
  • Route notes and maps 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 typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2849per person, tour only

  • 31 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)
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 typeSelf-guided cycling
  • Duration6 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
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 typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3149per person, tour only

  • 40 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)
Oxford to Bath Cycle
United Kingdom

Oxford to Bath Cycle

Cycle between Oxford, 'City of Dreaming Spires' and Bath, a UNESCO World Heritage City on an 8 night holiday riding along canal paths and quiet country roads. Discover pretty Cotswolds villages, Roman history and beautiful gardens along the way.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$3179per person, tour only
  • All accommodation
  • Breakfasts daily
  • High quality bikes provided
  • Headwater navigation provided
  • Luggage transfers between hotels
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$3479per 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)