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.
  • Eco-friendly holidays.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Gozo Activities

Please call for prices

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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.

Departures:
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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.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Walking in the French Caribbean

jardin malangas gardens

Please call for prices

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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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Walking on La Palma

View from the top of La Palma

From $2185 per person

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For anyone who loves walking, the beautiful island of La Palma packs the cleanest and greenest punch in the Canaries! From verdant lush forests in the north to dramatic volcanic craters further south, and from mountainous national park to the crashing Atlantic coast, La Palma has natural beauty in abundance - the entire island is a UNESCO Biosphere Reserve - yet because of the lack of any mass tourism development, it retains a calm and relaxed atmosphere reminiscent of a bygone era.

Departures:
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  • 7 nights, twin centre
  • All buffet breakfasts, 5 lunches and all 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.
  • Expert-led holidays.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Explore the high peaks.
  • Delightful island holidays.

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Highlights of Gozo Cycling

Sunset on Gozo beach

Please call for prices

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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.
  • Holidays to enhance your wellbeing.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Highlights of Tenerife Walk

Solo traveller stood by signpost

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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Islands of Sicily Walk

Taormina's Greek theatre

From $2090 per person

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Undoubtedly one of the most spectacular, varied and unique walks in our portfolio, taking in the beautiful Aeolian Islands as well as the immense and impressive Mount Etna - the largest active volcano in Europe!

Departures:
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  • 9 nights, hotel-to-hotel
  • All continental breakfasts
  • 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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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.

Departures:
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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

Coast in Menorca, Spain

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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Complimentary fruit basket and a small bottle of Cava

Walking on Gran Canaria

From Gran Canaria to Tenerife

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.
  • Eco-friendly holidays.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Explore the high peaks.
  • 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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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

Rovinj from the water

Please call for prices

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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.
  • Holidays to enhance your wellbeing.
  • 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

Please call for prices

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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.
  • Expert-led holidays.
  • Especailly good for solo travellers.
  • Follow stunning coastal routes.
  • Delightful island holidays.
  • Beautiful lakes and rivers.

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Exploring the Cinque Terre on foot

one of the 5 Cinque Terre and its coastline

From $2310 per person

Italy's beautiful Ligurian Coast is both chic and stunning! On this 9-night holiday, you'll visit exclusive Portofino, stay in charming Portovenere and explore the world-famous Cinque Terre, a UNESCO world heritage site, honoured by artists for centuries.

Departures:
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  • 9 nights, hotel-to-hotel
  • All buffet breakfast and 4 evening meals
  • 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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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.
  • Holidays to enhance your wellbeing.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Explore the high peaks.
  • Delightful island holidays.

View holiday

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

Please call for prices

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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.
  • Holidays to enhance your wellbeing.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Walking on La Gomera

Walking tour on The Canary Islands.

From $2275 per person

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Enjoy varied guided walking on the sub-tropical island of La Gomera. Stay in the **** Parador in the island capital of San Sebastian. Excellent cuisine, and spectacular gorge and coastal walks. Finish off the day with a dip in the pool overlooking Mount Teide on Tenerife.

Departures:
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  • 7 nights, single centre
  • All buffet breakfasts, 5 lunches all evening meals including wine included
  • Varied routes for nature lovers and botanists.
  • Destinations with bird watching opportunities.
  • Discover stunning historic sites en-route.
  • Lots of swimming opportunities.
  • Especailly good for solo travellers.
  • Perfect for couples.
  • Follow stunning coastal routes.
  • Delightful island holidays.

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Email: info@breakaway-adventures.com

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Customer ratings

Based on 729 customer reviews, the average satisfaction rating for Island based walking & cycling holidays is
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Headwater's Island based walking & cycling holidays 4.5610425240055 729
  • ATOL Protected (No. 9957)
  • IATA Registered
  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

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call us: 1-800-567-6286 or email: info@breakaway-adventures.com

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