A cycling holiday is one of the best ways to uncover a new destination. Exploring places on two wheels allows you to go further, faster, giving you ample opportunities to extend your time discovering places that interest you. On a Headwater cycling holiday, the possibilities are endless for every kind of cyclist.
You don't have to be at a Tour de France level to be able to enjoy a cycling holiday. Our relaxed routes are carefully designed to be stress-free, with meticulous turn-by-turn directions from RideWithGPS - the audio navigation individually created for every one of our cycling itineraries. All you need to do is take to the pedal and enjoy your cycling holiday, map-free, whether you choose to cycle past lavender fields and vineyards in Cotes du Ventoux, ride along the iconic canal district on our Amsterdam to Brussels trip or pedal along the dedicated cycle paths in County Kerry on the spectacular Wild Atlantic Way.
Think you'll be weighed down with luggage, think again - your belongings will be transported ahead for you so you can cycle at your own pace.
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.
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Explore the Cotswolds - England's largest Area of Outstanding Natural Beauty - by bike and on foot on this 7 night self-guided trip that includes stays in the villages of Moreton-in-Marsh, Winchcombe and Bourton-on-the-Water. Discover the beautiful rolling countryside, honey-coloured villages and stunning gardens and manor houses, all at your own pace.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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Stay in a luxury 4 star hotel - with top-of-the-range wellness centre - and choose from a whole host of activities: walking, cycling (route notes for both provided), water sports, boat trips, ice caves. Complimentary Headwater bikes included for the duration of your stay.
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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.
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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.
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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.
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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!
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Start at Matera, one of the oldest inhabited cities in the world and cycle through the Alta Murgia National Park, the largest natural park in Italy. Reach the Adriatic coastline at Trani, known as the 'Pearl of Puglia' and continue your ride, south, along the coast to Bari and your final destination, Monopoli.
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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.
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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.
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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'.
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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.
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Enjoy this short break, single centre trip with a choice of routes cycling from your base hotel in Amsterdam. Routes out of the city include the destinations of Volendam, Haarlem, Muiden and Zaandam, each with their own highlights. Discover Amsterdam, one of Europe's most intriguing cities where it has been suggested, for a long time, that there are more bicycles than people.
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Discover the delights of one of Europe’s most beautiful towns in Utrecht on this single centre cycling holiday. Well-planned routes, direct from the hotel in all directions, head out to discover areas of natural beauty including the New Dutch Waterline - an important military defence line in Dutch history as well as historical forts, castles and fortified towns.
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Discover the lakes and rivers of the Salzkammergut region of Austria on a self-guided cycling tour from your base at the family-run Hotel Goiserer Muhle in Bad Goisern. Explore the Imperial city of Bad Ischl and the World Heritage area around Lake Hallstatt and marvel at the surrounding landscape of peaks, lakes and rivers.
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A short break for an epicurean life style in Beaune, the wine capital of Burgundy to explore the world famous vineyards with prestigious wine estates as well as the fine local cuisine.
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A short break to relax in Chablis vineyards in a charming 4* hotel with spa. Enjoy fine cuisine including 1 gastronomic dinner and plenty of opportunities for great wine tasting at local producers.
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Follow the curves and bends of the Danube as it flows through steep-sided valleys and wide riverside woods towards beautiful Vienna. The densely wooded slopes and ravine forests help to create the setting for one of the most significant river landscapes of Central Europe; with the largely flat landscape perfectly suited to self-guided cycling. You will pass many delightful castles, ruins and abbeys whilst visiting historic towns such as Linz, Melk and Krems. The final destination of Vienna is the perfect place to explore, enjoy some great food and perhaps take in a concert.
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This linear cycling trip follows the artwork of the Flemish Masters and takes in the iconic cities of Belgium. Starting in fairytale Bruges, a UNESCO World Heritage Site, you head via the UNESCO City of Music of Ghent to the home of beer, antiques and diamonds in Antwerp and finishing in Brussels with it's fabulous Grand Place and many more historic sights.
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This linear cycling trip follows the artwork of the Flemish Masters and takes in the iconic cities of Belgium. Starting in Brussels with it's fabulous Grand Place and many more historic sights, to the home of beer, antiques and diamonds in Antwerp, via the UNESCO City of Music of Ghent and finishing in fairytale Bruges - a UNESCO World Heritage Site.
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Discover the cities of Amsterdam, Haarlem, Leiden, Delft and Gouda on this hotel-to-hotel trip around some of the favourite cities of Holland. Soak up these cultural gems whilst enjoying the idyllic Dutch countryside between them. Cycling distances are mostly relatively short so you can take the time to sightsee on arrival and in the morning before departing each city.
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This single-centre holiday in Southern Bavaria is a great choice for people wanting to explore the area around Lake Chiemsee at their own pace. Mountains, lakes, rivers and nature reserves make up some of the natural highlights of the region.
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Explore two of Europe's top capital cities - Amsterdam and Brussels - as well as the historical cities of Gouda and Antwerp, famous for their culinary and cultural contributions. This linear trip travels through the Green Heart of Holland with its canals and windmills and on through the Flemish Brabant region of Belgium.
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Combine a stay at the beach with a 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 a number of small coves, nearby, to explore. We provide a range of fully researched, self-guided walking and cycling routes, typically at Activity Level 1. A complimentary Headwater bike for your exclusive use throughout your stay is included to give you total flexibility.
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A relaxed 4 night tour between Auxerre and Chablis, cycling via rolling countryside, vineyards and canal paths to allow lazy riverside picnic breaks and world famous wine tasting.
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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.
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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.
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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.
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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.
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Cycle from the iconic leaning tower of Pisa to the Ponte Vecchio in Florence, passing through beautiful Tuscan landscape that inspired artists and composers such as Leonardo da Vinci and Puccini. The gentle cycling is mainly along riverside paths and quiet roads, and there are the opportunities to lengthen the rides, or take the train at some stages to spend extra time at your destinations.
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Spectacular riding from the stunning Dolomites to Venice. Starting from Bolzano, the capital of the South Tyrol, you'll follow gentle riverside tracks through fragrant orchards and vineyards to reach Lake Garda. Continue the ride through the beautiful cities of Verona, Padova and finally exploring the canals and waterways of Venice.
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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.
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Ride the famous 'Loire a velo' cycling path from Tours to Angers. The Loire Valley is classified as UNESCO Natural World Heritage. All along the route, you stick closely to France’s last great wild river, with its sandy banks and islands, its vine-covered slopes, its typical towns and villages, its fine food and its unique atmosphere.
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All the greatest chateaux of the Loire in a short break. Bike from a chateau to another is just a short ride. Through the vineyards, on peaceful bike routes or along the Loire river, discover the royal Loire Valley.
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Walking and cycling activity in Chablis vineyards. Set in a gastronomic boutique hotel with spa, this tour allow you to choose everyday your adventure. Ideal for food and wine lovers to explore the Burgundy world famous vineyard.
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This longer version of our Pearls of Holland trip cuts the last day's 80km route into two shorter sections with a stop in historical Woerden. Discover the cities of Amsterdam, Haarlem, Leiden, Delft and Gouda on this hotel-to-hotel trip around some of the favourite cities of Holland. Soak up these cultural gems whilst enjoying the idyllic Dutch countryside between them. Cycling distances are relatively short so you can take the time to sightsee on arrival and in the morning before departing each city.
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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.
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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.
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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.
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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.
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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.
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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.
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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 Pinhao.
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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.
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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.
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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.
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All the greatest chateaux of the Loire are waiting for you during this short break. Bike from a chateau to another is just a short ride. Through the vineyards, on peaceful bike routes or along the Loire river, discover the royal Loire Valley. With a selection of 4* hotel accommodations, experience an unforgettable journey.
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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).
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Ride the famous 'Loire a velo' cycling path from Tours to Angers. The Loire Valley is classified as UNESCO Natural World Heritage. All along the route, you stick closely to France’s last great wild river, with its sandy banks and islands, its vine-covered slopes, its typical towns and villages, its fine food and its unique atmosphere. Enjoy deluxe accommodation with a selection of charming 4 star hotels.
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A coastal ride through the best Normandy's highlights : from the historical and emotional vestiges of the World War II, to the colourful harbour of Honfleur passing via the charming and elegant Deauville seaside resort.
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An invitation to the world famous Grands Crus of Burgundy. Between Beaune and Vougeot, enjoy a peaceful cycling through the amazing wine villages. As great cuisine pairs with great wine, prepare your taste buds for fine cuisine.
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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.
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Discover the greatest highlights of Brittany: The World Wonder Mont St Michel, the spectacular Emerald Coast and the gorgeously preserved mediaeval walled towns of St Malo and Dinan.
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Explore the undiscovered western coast of Sicily by bike to find pristine nature reserves, ancient monuments and Baroque towns. Highlights include Segetsa amphitheatre and Selinunte Archeaological Park.
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From Beaune explore the world famous vineyards with prestigious wine villages and continue south along a canal on a very peaceful cycling path going through Romanesque towns and undulating landscapes to Macon.
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All the greatest chateaux of the Loire are waiting for you. Bike from a chateau to another is just a short ride. Through the vineyards, on peaceful bike routes or along the Loire river, discover the royal Loire Valley.
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Easy cycling across Mallorca, taking in coastal trails and beautiful inland routes
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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.
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County Kerry contains some of Ireland's most iconic scenery, with sea cliffs carved by the wild Atlantic Ocean, and soft golden baches, emerald-green farmland criss-crossed by stone walls, mist-shrouded bogs and cloud-torn mountain peaks.
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A very gentle linear route following the course of the River Danube - arguably the most beautiful river in Europe. Highlights include Passau 'City of Three Rivers', medieval Linz, the UNESCO Wachau Valley and Benedictine Melk!
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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.
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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.
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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.
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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.
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This 10-night holiday combines gentle pedalling through olive groves, sunflower fields and vineyards with time in gorgeous historic towns and sun-drenched villages with 4 nights spent in Spoleto with its fantastic architecture and opportunities to visit Rome and Norcia, famed for its cured meats.
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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.
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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!
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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.
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All the greatest chateaux of the Loire are waiting for you. Bike from a chateau to another is just a short ride. Through the vineyards, on peaceful bike routes or along the Loire river, discover the royal Loire Valley. With a selection of 4* hotel accommodations, experience an unforgettable journey.
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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.
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Combine three of our exciting holidays to experience the ultimate activity holiday in the Dordogne. 2 days of safe, undemanding canoeing with a choice of leisurely walking or cycling on the other days.
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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!
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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.
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Start at Matera, one of the oldest inhabited cities in the world and a UNESCO World Heritage site and cycle through the Alta Murgia National Park. Follow the Adriatic coastline between Trani and Bari before heading inland through unspoilt villages and gently rolling hills. Discover Alberobello, with its trulli houses, and the white village of Ostuni as you wind your way back towards the sea.
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Guided group cycling, with peaceful coastal routes along the spectacular Dalmatian coastline, from Hvar to Dubrovnik.
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Enjoy the spectacular scenery of the Dolomites by bike while avoiding the need to ride up any long climbs. We explore the beautiful valleys of the Alta Pusteria, visiting Brunico, Lake Toblach, Cortina d’Ampezzo and crossing into the Austrian Tyrol to explore mediaeval Lienz. We stay in a family-run three-star hotel in Dobbiaco with a spa and swimming pool.
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Experience the wild beauty of the South Coast of Wales on a week's cycling adventure. Pass through the Gower Peninsula AONB to discover stunning coastal views, bucolic villages and farmland, and charming villages full of Welsh hospitality.
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Discover the culture and history of the Scottish Highlands on two wheels, with some of the most evocative, dramatic scenery in the world. This sparsely populated, mountainous region has a history, culture and climate all of its own.
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Our week of guided cycling is a journey through fascinating classical history and a superb variety of landscapes, from the azure blue of the sea to the green olive trees and vineyards of the heart of Greece.
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Follow scenic coastal routes along the Atlantic Coast of Portugal. This tour starts in Porto, with highlights including a scenic ride through the dunes of the Sao Jacinto Natural Reserve and an overnight in the picture-perfect fortified village of Obidos.
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Cycle around four iconic lakes in two countries - Italy and Switzerland. Visit Lake Orta, Lake Como, Lake Maggiore and Lake Lugano.
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Cycle through vineyards, over mountain passes and along South Africa's most spectacular coastline. This tour provides 9 days of guided cycling with full vehicle support.
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Ride through three countries with divergent histories and subtly different cultures. From the bustling streets of Bangkok, Thailand to the serene tranquillity of the shimmering paddy fields, to the magnificence of Angkor Wat’s temples in Cambodia, we see a little piece of everything these amazing countries have to offer. In Vietnam we enter the Mekong Delta, a spectacular patchwork of rice paddies and waterways.
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Cycle from the Western Ghats to the idyllic coastline of Kerala. Beautiful landscapes, fascinating towns, stunning beaches and superb food, southern India is an excellent place to explore by bike. We cycle through colourful villages where rural life has remained little-changed for centuries and even stay overnight on a Keralan houseboat.
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