On our cycling holidays you move on between hotels every two days, and we transport your bags, so when you're cycling you don't need to carry a lot in your panniers and you're free to travel at your own pace. In-between days are a great opportunity for local exploring or for relaxing by the pool! We've a wide range of cycling holidays to choose from, for all abilities.
Click on the appropriate 'View Holiday' button for full holiday details or take a look at our activities section for further information about how our cycling holidays work.
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Secrets of San Gimignano Cycling
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Cycling holiday in Italy | Hotel-to-hotel | Upper 2 bikes
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 panormic pools - views extend as far as Corsica on a clear day!
Departures: JFMAMJJASOND
Contrasts of Catalunya Cycling
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Cycling holiday in Spain | Hotel-to-hotel | 1 bike
Packed with contrasts and variety, this easy 6-night cycling tour takes in the unspoilt Catalan coast, passing through olive groves, peach orchards and stunningly beautiful sun-coloured villages. All the hotels have pools, and 2 nights are spent in a luxury C14 castle.
Departures: JFMAMJJASOND
Contrasts of the Alentejo Cycling
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Cycling holiday in Portugal | Hotel-to-hotel | Upper 1 bike
With 300+ days of sunshine a year, it's little wonder that this holiday is such a winner with Headwater cyclists! But it's not just the weather: Portugal's Alentejo offers wonderfully deserted beaches, tiny white villages, gently rolling hills and colourful fishing harbours - all untouched by tourism.
Departures: JFMAMJJASOND
Heart of Provence Cycling
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Cycling holiday in France | Hotel-to-hotel | 2 bikes
There are few better places to explore by bike than Provence: ancient villages, sleepy squares, olive groves, vineyards and fields of lavender stretching as far as the eye can see. All hotels have private pools.
Departures: JFMAMJJASOND
Highlights of Gozo Cycling
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Cycling holiday in Gozo | Hotel-to-hotel | Lower 1 bike
Wonderfully easy year-round cycling staying in luxury hotels - all with pools - and taking in ancient archaelogical treasures, hidden hilltop hamlets and colourful fishing villages. Beautful bays and stunning turquoise seas. Exceptional value for money too.
Departures: JFMAMJJASOND
Secrets of Cyprus Cycling
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Cycling holiday in Cyprus | Hotel-to-hotel | Upper 2 bikes
A slightly challenging circuit following a loop around Cyprus' north western corner, this holiday is a perfect choice for keen bird-watchers looking for an out of season break. You'll stay in a variety of family-run hotels and the coast is never far away if you fancy a dip!
Departures: JFMAMJJASOND
Abbeys and Vineyards Cycling
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Cycling holiday in France | Hotel-to-hotel | 1 bike
An easy 6-night cycling holiday, perfect for people looking for a short break. World-famous wines (lots of tasting opportunities!), forgotten country villages, superb local cuisine.
Departures: JFMAMJJASOND
Aspects of Assisi Cycling
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Cycling holiday in Italy | Hotel-to-hotel | Lower 2 bikes
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 mediaeval Bevagna, Etruscan Perugia, picture-postcard Spello and ancient Assisi.
Departures: JFMAMJJASOND
Atlantic Coast Cycling
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Cycling holiday in Portugal | Hotel-to-hotel | Lower 2 bikes
This luxury cycling tour follows a linear route from the countryside to the Atlantic coast, and takes in en route verdant valleys, hilltop castles, lush forests and wild deserted beaches. You can extend your stay too to include time in cosmopolitan Lisbon.
Departures: JFMAMJJASOND
Austrian Lakes Cycling
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Cycling holiday in Austria | Hotel-to-hotel | Choose 1 or 2 bikes
The flexibility of this holiday make it an outright winner for families looking for gentle traffic-free cycling with lots more to do besides: pools, watersports, mountain rail rides, boat trips.
Departures: JFMAMJJASOND
Chateaux of the Loire Cycling
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Cycling holiday in France | Hotel-to-hotel | Lower 2 bikes
An interest-packed, gentle cycling holiday crammed with historic and cultural highlights: pretty wine villages, charming mediaeval towns and world-famous wines in abundance! Superb cuisine throughout too
Departures: JFMAMJJASOND
Classic Burgundy Cycling
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Cycling holiday in France | Hotel-to-hotel | 1 bike
This 8-night cycling holiday really gets under the skin of Burgundy: its people, its villages, its waterways and, of course, its world-famous wines. The days have been specially designed to allow for lazy riverside lunches and gastronomic pit-stops!
Departures: JFMAMJJASOND
Classic Catalan Cycling
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Cycling holiday in Spain | Hotel-to-hotel | 2 bikes
This 10-night holiday explores the wonderfully undiscovered Catalan countryside, a region of pine-fringed valleys dotted with historic castles, hilltop fortresses, ancient wine villages and fields full of lavender. It's wonderfully quiet cycling too - and hardly a tourist in sight!
Departures: JFMAMJJASOND
Classic Lot Cycling
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Cycling holiday in France | Hotel-to-hotel | 2 bikes
This holiday explores the 'real' France: majestic rivers, endless patchwork fields, pink-gold cliffs and ancient villages and chateaux. Often, it's as though you've got the countryside wholly to yourselves! Excellent choice too for lovers of fine food and wine.
Departures: JFMAMJJASOND
Classic Wye Valley Cycling
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Cycling holiday in Great Britain | Hotel-to-hotel | 1 bike
A popular 5-night cycling circuit taking in the quintessential British Wye Valley: Iron Age forts, the Black Mountains, the Welsh Marches and the lovely market town of Ludlow, food capital of central England!
Departures: JFMAMJJASOND
Coastal Croatia Cycling
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Cycling holiday in Croatia | Hotel-to-hotel | Upper 1 bike
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.
Departures: JFMAMJJASOND
Contrasts of Puglia Cycling
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Cycling holiday in Italy | Hotel-to-hotel | 2 bikes
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.
Departures: JFMAMJJASOND
Cycling in Emilia Romagna
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Cycling holiday in Italy | Hotel-to-hotel | Upper 1 bike
One of the flattest cycling routes in our programme, this is a great holiday for older couples or first timers. Highlights include gorgeous Comacchio, historic Ravenna and the splendid Renaisance city of Ferrara.
Departures: JFMAMJJASOND
Dordogne Gastronomic Cycling
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Cycling holiday in France | Hotel-to-hotel | 2 bikes
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.
Departures: JFMAMJJASOND
Emerald Coast Cycling
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Cycling holiday in France | Hotel-to-hotel | Lower 2 bikes
Visitors have long been drawn to the stunning white beaches of Brittany's Emerald Coast, yet the region remains largely unspoiled with traditional fishing ports, colourful country hamlets and beautifully preserved walled towns unchanged since the Middle Ages.
Departures: JFMAMJJASOND
Gastronomic Barolo Cycling
From Please call
Cycling holiday in Italy | Hotel-to-hotel | 2 bikes
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.
Departures: JFMAMJJASOND
Heart of Venetia Cycling
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Cycling holiday in Italy | Single centre | Choose 1 or 2 bikes
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.
Departures: JFMAMJJASOND
Hidden Valleys and Villages
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Cycling holiday in France | Hotel-to-hotel | 2 bikes
The Lot remains undoubtedly one of France's least spoiled regions, with dramatic views at every turn: forgotten valleys, cliff-hanging villages, mediaeval towns and world-famous pre-historic sites. Wonderfully friendly hotels too.
Departures: JFMAMJJASOND
Highlights of Holland Cycling
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Cycling holiday in Holland | Hotel-to-hotel | 1 bike
Travel from dunes and beaches to canals and windmills as you explore the beautiful, flower filled region of north west Holland, more than half of which has been reclaimed from the sea. Easy, varied and rewarding cycling on routes you can easily adapt for longer/shorter days.
Departures: JFMAMJJASOND
Lake Constance Cycling
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Cycling holiday in Austria | Hotel-to-hotel | Choose 1 or 2 bikes
With over 300kms of pancake flat 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!
Departures: JFMAMJJASOND
Loire Gastronomic Cycling
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Cycling holiday in France | Hotel-to-hotel | Lower 1 bike
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.
Departures: JFMAMJJASOND
Passau to Vienna Cycling
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Cycling holiday in Austria | Hotel-to-hotel | 1 bike
A very gentle linear route following the course of the River Danube - arguably the most beautiful river in Europe. Highlights include mediaeval Linz, UNESCO Krems and Benedectine Melk - stunning 360 views at every turn!
Departures: JFMAMJJASOND
Porto to Coimbra Cycling
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Cycling holiday in Portugal | Hotel-to-hotel | 1 bike
Pancake-flat 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 taking in vibrant market towns and seaside marinas before ending in Coimbra, Portugal's capital in the Middle Ages.
Departures: JFMAMJJASOND
Rivers and Vineyards Cycling
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Cycling holiday in France | Hotel-to-hotel | 2 bikes
Cycling along traffic-free lanes through vineyards, orchards and flower-festooned beautiful villages, this off-beat holiday is rich in historic and gastronomic treasures! 6 nights are spent in France - with 2 nights eating in a Michelin-starred restaurant - and 2 nights in Germany.
Departures: JFMAMJJASOND
Secret Provence Cycling
From Please call
Cycling holiday in France | Hotel-to-hotel | 2 bikes
Choose from an 8 or 10 night version of this popular cycling holiday in timeless and sun-drenched Provence. You'll cycle through picturesque villages and vineyards, and past hidden castles and churches. Two nights are spent by the Gorges de Verdon.
Departures: JFMAMJJASOND
Secrets of Sicily Cycling
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Cycling holiday in Italy | Hotel-to-hotel | 2 bikes
This 8-night cycling route explores Sicily's unspoilt western coast, a sun-drenched landscape of golden bays, azure waters, swaying vines and tiny farming hamlets unchanged over the years. Lots of historic interest too: mediaeval Erice, ancient Segesta and sea-facing Marsala.
Departures: JFMAMJJASOND
Swiss Lakes Cycling
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Cycling holiday in Switzerland | Hotel-to-hotel | 1 bike
Beautifully flat traffic-free trails make this a popular cycling choice for novices or families with children. The route takes you via pretty riverside villages, past chic waterfront marinas and through protected nature reserves linked by sun-dappled trails.
Departures: JFMAMJJASOND
Vaucluse Vineyards Cycling
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Cycling holiday in France | Hotel-to-hotel | Upper 1 bike
A feast for foodies, 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.
Departures: JFMAMJJASOND
Villas and Vineyards Cycling
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Cycling holiday in Italy | Hotel-to-hotel | 1 bike
Wonderfully flat 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.
