Level 2 cycling holidays

Our level 2 tours offer more varied cycling terrain which will appeal to the fairweather cyclist, or to more active riders looking for a relaxed trip. No special technical skills are required.

A Taste of Sicily Cycling

Ragusa Ibla

From $2790 per person

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This ten-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.

Departures:
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  • 10 nights, hotel-to-hotel
  • All continental breakfasts and 6 evening meals
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Aspects of Assisi Cycling

Leaving Assisi on a bike

From $1845 per person

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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 mediaeval Bevagna, Etruscan Perugia, picture-postcard Spello and ancient Assisi.

Departures:
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  • 8 nights, hotel-to-hotel
  • All breakfasts and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Option to hire electric bikes.

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Classic Catalan Cycling

Callela from Cami de Ronda

From $1950 per person

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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 beautiful countryside. It's wonderfully quiet cycling too, where you can discover unspoilt Catalunya.

Departures:
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  • 10 nights, hotel-to-hotel
  • All continental breakfasts and 2 evening meals included
  • Holidays with gastronomic meals.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.

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Classic Chianti Cycling

San Gimignano city  from Tuscan countryside.

From $2445 per person

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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!

Departures:
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  • 10 nights, hotel-to-hotel
  • All buffet breakfasts and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.

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Contrasts of Andalucia Cycling

Square in Vejer

From $1470 per person

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This 7 night holiday takes in a contrast of wonderfully scenic cycling mixed in with a large blast of culture and history. From Jerez, home to sherry and flamenco, through the stunning hilltop ‘Pueblos Blancos’ to bustling old world Cadiz, with its beautiful sandy beaches.

Departures:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.

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Contrasts of the River Ebro Cycling

Along the River Ebro to the sea

From $2045 per person

Boasting two historically-rich provincial capitals, southern Catalunya is idyllic and rural – rich in birdlife, wetlands and rice fields – as well as a gorgeous coastline. The Costa Daurada coastline stretches from just north of Tarragona to the Delta de l’Ebre – with a wonderful mix of country, riverside and coastal trails, the Terres de l’Ebre UNESCO Biosphere Reserve has two national parks and 88 miles of coastline, perfect for exploring by bike.

Departures:
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  • 10 nights, hotel-to-hotel
  • All buffet breakfasts and 8 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Eco-friendly holidays.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Good choice for families.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.

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Cycling in 'The Real Algarve'

Henry the Navigator

From $1500 per person

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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.

Departures:
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  • 6 nights, hotel-to-hotel
  • All continental breakfasts, and 5 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.

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Dordogne Gastronomic Cycling

 Beynac Castle - Dordogne - France

From $2155 per person

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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.

Departures:
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  • 8 nights, hotel-to-hotel
  • All continental breakfast and gastronomic evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Beautiful lakes and rivers.
  • Option to hire electric bikes.

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Dorset and the Jurassic Coast Cycling

Durdle Door near Lulworth on the Jurassic Coast

From $882 per person

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Spend five nights taking in the best bits of one of England's most beautiful counties, featuring some of its most spectacular coastline along the UNESCO listed Jurassic Coast. Whether you're riding alongside unspoilt beaches, exploring the ruins of a crumbling National Trust castle, visiting a protected nature reserve, or enjoying lunch in a historic seaside town, this spectacular independent ride will show you England's south coast at its glorious best!

Departures:
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  • 5 nights, hotel-to-hotel
  • Full English Breakfasts included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.
  • Option to hire electric bikes.

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Five Waterways of Bavaria Cycling

Nuremburg

From $2122 per person

Welcome to the Fünf-Flüsse-Radweg, one of Bavaria’s long-distance cycle routes. This circular route starts in the UNESCO mediaeval city of Regensburg and takes you on a 10-night journey through the north-east of Bavaria. You’ll follow a series of well-networked paths along a mix of waterways: the majestic Danube, the stunning Altmühl, the Main-Danube Canal, the tiny Pegnitz and the beautiful Naab.

Departures:
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  • 10 nights, hotel-to-hotel
  • 8 nights bed and breakfast 2 nights half board
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Great vegetarian meal options.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Good choice for families.
  • Beautiful lakes and rivers.

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Gastronomic Barolo Cycling

The UNESCO recognised Langhe hills

From $2480 per person

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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.

Departures:
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  • 8 nights, hotel-to-hotel
  • All buffet breakfasts and gastronomic evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Option to hire electric bikes.

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Gastronomic Burgundy Cycling

Chateau de pommard

From $2120 per person

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Gastronomic meals and world famous wines, mediaeval towns and traditional villages, historic hotels and chateaux, and the picturesque Canal de Bourgogne. These are some of the highlights of this 6 night cycle around the beautiful Cote D'Or along quiet lanes, vineyard tracks and tranquil waterside paths.

Departures:
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  • 6 nights, hotel-to-hotel
  • All continental breakfasts and gastronomic evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Perfect for couples.
  • Beautiful lakes and rivers.
  • Option to hire electric bikes.

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Hilltop Villages of Provence Cycling

The perched village of Gordes

From $1795 per person

*****

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.

Departures:
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  • 6 nights, hotel-to-hotel
  • All continental breakfasts and 4 evening meals included
  • Holidays with wine-tasting opportunities.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Beautiful lakes and rivers.
  • Option to hire electric bikes.

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Italian Alps to Lake Garda Cycling

Torbole, Trentino

From $2030 per person

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Soak up the natural beauty of northern Italy's timeless mountain scenery in the provinces of South Tyrol and Trentino, as you ride from the alpine pass at Resia to the shores of Lake Garda. The cycling is mostly along riverside cycle paths, through orchards and vineyards, with a backdrop of lakes and mountains, and you'll discover the historic cities of Merano, Bolzano and Trento along the way.

Departures:
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  • 9 nights, hotel-to-hotel
  • All buffet breakfasts and 3 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Beautiful lakes and rivers.

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Landscapes of the Luberon Cycling

Bonnieux

From $2155 per person

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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.

Departures:
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  • 8 nights, hotel-to-hotel
  • All continental breakfasts and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Beautiful lakes and rivers.
  • Option to hire electric bikes.

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Mediaeval Umbrian Cycling

Cycle to Eggi

From $2030 per person

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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.

Departures:
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  • 10 nights, hotel-to-hotel
  • Continental breakfast and 6 evening meals
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Option to hire electric bikes.

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Secrets of San Gimignano Cycling

Poppy field with San Ginignano town

From $2015 per person

****#

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!

Departures:
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  • 8 nights, hotel-to-hotel
  • All continental breakfasts and 6 evening meals included
  • Holidays with gastronomic meals.
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Eco-friendly holidays.
  • Perfect for couples.

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Secrets of Sicily Cycling

Scopello coast, Sicily

From $1765 per person

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This 7-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:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts and 6 evening meals included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.
  • Option to hire electric bikes.

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Undiscovered Southern Catalunya Cycling

A boat on the Ebro

From $1750 per person

*****

Explore Southern Catalunya, favoured by Picasso, by bike on a mixture of riverside paths, via verde and quiet roads. This is 'real' Spain with lively towns and charming villages with a backdrop of coast or mountains.

Departures:
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  • 8 nights, hotel-to-hotel
  • All buffet breakfasts and 6 evening meals included
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.

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Waterways & Wine Villages of the Canal du Midi

Beziers

From $1500 per person

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On this six-night cycling holiday you’ll enjoy a wonderful, scenic loop of the cities and waterways which surround the picturesque and UNESCO-recognised Canal du Midi. Keeping the canal within close proximity you’ll follow its course along quiet roads and tracks, enjoying its scenic tributaries and impressive structures, and discovering mediaeval villages and towns, renowned wine regions and a wonderful variety of birdlife along the way.

Departures:
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  • 6 nights, hotel-to-hotel
  • All continental breakfasts
  • Holidays with wine-tasting opportunities.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Beautiful lakes and rivers.

View holiday

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Customer ratings

Based on 315 customer reviews, the average satisfaction rating for Level 2 cycling holidays is ****#

Click here to read customer reviews

Headwater's Level 2 cycling holidays 4.6150793650794 315
  • ATOL Protected (No. 9957)
  • IATA Registered
  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

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