Island based walking & cycling holidays

Across the range of Headwater islands are some of the most spectacular sights in Europe from the astonishingly beautiful Aeolian Islands - a string of seven volcanic islets that glimmer like black pearls off Sicily's unspoilt coast - to Crete's lush Samaria Gorge, the longest in Europe, to Capri, "Pearl of Naples" and the most beautiful island in the Med. Other islands, such as the Azores and Canaries lie on the main migratory routes from Africa and are a bird-spotters paradise, while Gozo's lemon groves, figs and peaches flourish in the temperate year-round climate.

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.

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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.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Gozo Activities

From $1720 per person

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Explore the small and beautiful island of Gozo on foot and by bike to discover breathtaking views, idyllic villages and amazing historic sites. Gentle routes by day, and 5-star luxury by night, make this perfect for first-timers.

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  • 7 nights, twin centre
  • All buffet breakfasts and evening meals included
  • Holidays with gastronomic meals.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Walking in the French Caribbean

jardin malangas gardens

From $3625 per person

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The islands of Martinique and Guadeloupe both have a distinctly French flavour - from familiar yellow post boxes to freshly baked baguettes every morning! Out walking, you'll enjoy verdant volcanic hills, swaying sugarcane, banana plantations and palm-fringed beaches.

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  • 13 nights, twin centre
  • All continental breakfasts and 11 evening meals included
  • Holidays with gastronomic meals.
  • Varied routes for nature lovers and botanists.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Highlights of Gozo Cycling

Sunset on Gozo beach

From $1410 per person

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Wonderfully easy year-round cycling staying in luxury hotels with superb swimming pools and taking in ancient archaelogical treasures, hidden hilltop hamlets and colourful fishing villages. Beautiful bays and stunning turquoise seas.

Departures:
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  • 6 nights, hotel-to-hotel
  • All buffet breakfasts and evening meals included
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Highlights of Tenerife Walk

Views over Tenerife

From $1255 per person

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Most visitors know Tenerife for its south coast tourist resorts, but head inland and you have an incredible variety of landscapes to explore: plunging valleys, protected forest and tiny white villages where locals welcome walkers with open arms!

Departures:
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  • 7 nights, twin centre
  • All buffet breakfasts and 3 evening meals included
  • Varied routes for nature lovers and botanists.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Islands of Bermuda Walk

From $2415 per person

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Famed for its stunning turquoise waters and pink sand beaches, the stunning archipelago of Bermuda is a tiny historic treasure trove packed with natural beauty - flowers, fish, birds - and fabulous year-round sunshine.

Departures:
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  • 7 nights, single centre
  • All buffet breakfasts and 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.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Marvels of Madeira Walk

Madeira coastline

From $1610 per person

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Perfect for year-round walking, the floating garden of Madeira is a paradise of tropical flowers, exotic birds and trees, romantic gorges and emerald seas. Luxury 4 and 5 star hotels throughout provide exquisite local cuisine with possibility of sampling the island's famous full-bodied wine.

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  • 7 nights, hotel-to-hotel
  • All continental breakfasts, 2 picnics and all evening 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.
  • Holidays to enhance your wellbeing.
  • Delightful island holidays.

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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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Secrets of Sicily Walking

Walking in the Zingaro Nature Reserve

From $1565 per person

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This triple centre holiday explores the unspoilt north western tip of Sicily and the nearby Egadi islands. It's a relatively undiscovered region where highlights include pristine sandy beaches, coral-lined grottoes, ancient hill villages and marvellously preserved nature reserves.

Departures:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts and 3 evening meals
  • 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.

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Walking the Coastal Trails of Menorca

Mao, Menorca

From $1315 per person

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Easy, tranquil walking based in the north western corner of Menorca, but including a hire car so you can easily explore the entire tiny island. It offers a rich cultural history, deserted white beaches and is a UNESCO protected Biosphere Reserve.

Departures:
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  • 7 nights, single centre
  • All continental breakfasts and evening meals
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Galapagos Voyage - Darwin's Enchanted Isles

Deck of MV Evolution

Please call for prices

Discover the beauty of seven of the Galapagos Islands on our 9 night itinerary, staying on the MV Evolution. Highlights include walking to the top of Bartlome for a view of iconic Pinnacle Rock, one of Galapagos' most photographed sites, and exploring the archipelago's oldest and youngest islands,

Departures:
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  • 9 nights, twin centre
  • 9 breakfasts, 7 lunches and 7 dinners included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Galapagos Voyage Central & Remote Northern Islands

Al Fresco dining on MV Evolution

Please call for prices

Our 9 night tour of the Galapagos takes in 9 of the Central and Northern Galapagos Islands from our base, the MV Evolution. Highlights include Post Office Bay and crossing the equator to Genovesa Island.

Departures:
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  • 9 nights, twin centre
  • 9 breakfasts, 7 lunches and 7 dinners included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Lots of swimming opportunities.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Complimentary fruit basket and a small bottle of Cava

Walking on Gran Canaria

Nature and landscape of the Canary Islands - Mountains of Gran Canaria

From $1270 per person

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Less than 100 miles off the northwest coast of Africa, in the centre of the Canaries Atlantic Archipelago, the volcanic island of Gran Canaria – roughly the same size as Greater London – is often referred to as “a continent in miniature” with its extraordinarily varied landscapes ranging from lush green forests and valleys in the north, to the towering mountainous interior, to the desert-like dunes and beautiful white beaches of its southern shores.

Departures:
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  • 7 nights, twin centre
  • All buffet breakfasts and evening meals included
  • Holidays with gastronomic meals.
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Explore the high peaks.
  • Delightful island holidays.

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Amalfi to Sorrento Walk

Looking out at the view over the Amalfi Coast

From $2060 per person

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There are few places in Italy as stunning as the Amalfi Coast with its emerald seas, plunging gorges and pastel villages linked by ancient walking paths. This linear walk follows the coast from elegant Amalfi to chic Sorrento, taking in en route vertical Positano and (optional) the beautiful island of Capri.

Departures:
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  • 8 nights, hotel-to-hotel
  • All buffet breakfasts and 3 evening meals included
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Coastal Croatia - Pula to Porec Cycling

Traditional kazuni

From $1485 per person

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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.

Departures:
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  • 7 nights, hotel-to-hotel
  • All continental breakfasts and 1 brunch 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.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Contrasts of Sardinia Walk

Cala Fuili Beach, Gulf of Orosei

From $2045 per person

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Beyond the sandy beaches and millionaires' yachts, Sardinia offers a land of shepherds' huts, traditional villages and tranquil valleys aching to be explored. On this twin centre holiday, you'll spend 3 nights inland before heading to the coast where you'll enjoy deserted white beaches and colourful fishing ports.

Departures:
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  • 7 nights, twin centre
  • All buffet breakfasts, 3 lunches and all evening meals
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Especailly good for solo travellers.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Delights of the Dalmatian Coast Walk

Vanja, Delights of the Dalmatian Coast guide

From $2325 per person

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Croatia's rich cultural heritage is matched only by its amazing natural beauty: sandy beaches, unspoilt islands, tourist-free villages and barely-visited historic sites - all perfect for exploring on foot. Lovely walks and super hotels including 5-star luxury in Dubrovnik.

Departures:
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  • 7 nights, hotel-to-hotel
  • All meals
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Especailly good for solo travellers.
  • Follow stunning coastal routes.
  • Delightful island holidays.
  • Beautiful lakes and rivers.

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Secrets of Tenerife Walk

Solo traveller

From $2260 per person

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A naturalist's paradise, the climate in Tenerife is so perfect for wild flowers, butterflies and birdlife that our walks are an explosive celebration of colour: at sea level, swaying banana palms contrast with yellow cacti, while inland hibiscus and geraniums adorn traditional white villages.

Departures:
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  • 7 nights, single centre
  • All buffet breakfasts, 5 lunches and all evening meals (including wine) included
  • Holidays with gastronomic meals.
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Explore the high peaks.
  • Delightful island holidays.

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The Amalfi Coast Walk

Walkers on clifftop path

From $2060 per person

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The Amalfi Coast is renowned for its sensational scenery - the mountains drop into crystal blue seas and the towns cling vertiginously to limestone cliffs. You'll visit stunning Pompeii and stay in elegant Ravello where 'must see' sights include Moorish Vila Rufolo and its semi-tropical gardens.

Departures:
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  • 7 nights, twin centre
  • All continental breakfasts and evening meals
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Especailly good for solo travellers.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Walking on Gozo - Calypso's Isle

Rough seas at Azure Window in Gozo, Malta

From $1205 per person

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Based at the exclusive 5-star Ta Cenc Hotel, the tiny island of Gozo offers secluded beaches, Arabic-style honey-coloured houses, lemon groves, palm trees, red GPO phone boxes and 'Dixon of Dock Green' police stations!

Departures:
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  • 7 nights, single centre
  • All buffet breakfasts and evening meals included
  • Varied routes for nature lovers and botanists.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Great vegetarian meal options.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Based on 730 customer reviews, the average satisfaction rating for Island based walking & cycling holidays is
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Headwater's Island based walking & cycling holidays 4.5599315068493 730
  • ATOL Protected (No. 9957)
  • IATA Registered
  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

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