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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.


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$2379per person, tour only

  • 57 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)
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$3449per person, tour only

  • 58 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)
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$2249per 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)
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$2449per person, tour only

  • 107 Reviews
  • All accommodation
  • All continental breakfasts and 2 evening meals
  • High quality bikes provided
  • GPS route 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 typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2749per person, tour only

  • 39 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)
Loire Gastronomic Cycling
France: The Loire

Loire Gastronomic Cycling

A gentle, unhurried introduction to the very essence of the Loire Valley: majestic chateaux, wide rivers, world-famous wines and some of the finest food we've ever eaten in France! Holiday includes two nights in a luxury chateau.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From US$2749per person, tour only

  • 81 Reviews
  • All accommodation
  • All continental breakfast and gastronomic 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

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$2779per person, tour only

  • 27 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$3449per person, tour only

  • 71 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)