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.
This single-centre cycling holiday allows you to explore the area around Bavaria’s Lake Chiemsee at your leisure. Enjoy spectacular mountain views, swimming in the lake and a wealth of historic and natural sites to visit.
DEPARTURE MONTHS
A circular route taking you from Augsburg, through villages and lakes, to the foothills of the Bavarian Alps and the fairytale castles of Neuschwanstein and Hohenschwangau before following the Romantic Road back to Augsburg.
DEPARTURE MONTHS
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
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
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
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
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
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
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
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
