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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.

View 23 holidays below


The Amalfi Coast Walk

The Amalfi Coast Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £1399per person, tour only

  • 37 Reviews
  • All continental breakfasts and evening meals
  • Led by experienced local guide
Delights of the Dalmatian Coast Walk

Delights of the Dalmatian Coast Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1539per person, tour only

  • 47 Reviews
  • All meals
  • Led by experienced local guide
Coastal Croatia  - Pula to Porec Cycling

Coastal Croatia - Pula to Porec Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From Call usper person, tour only

  • 81 Reviews
  • All continental breakfasts and 1 brunch included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Walking on Gozo - Calypso's Isle

Walking on Gozo - Calypso's Isle

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £704per person, tour only

  • 90 Reviews
  • All buffet breakfasts and evening meals included
  • Route notes and maps provided
Highlights of Tenerife Walk

Highlights of Tenerife Walk

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £767per person, tour only

  • 29 Reviews
  • All buffet breakfasts and 3 evening meals included
  • Route notes and maps provided
  • Luggage transfers between hotels
Highlights of Gozo Cycling - Short Break

Highlights of Gozo Cycling - Short Break

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration4 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £779per person, tour only
  • All buffet breakfasts and evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Walking on Gran Canaria

Walking on Gran Canaria

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £839per person, tour only

  • 16 Reviews
  • All buffet breakfasts and evening meals included
  • Route notes and maps provided
  • Luggage transfers between hotels
Walking the Coastal Trails of Menorca

Walking the Coastal Trails of Menorca

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £849per person, tour only

  • 45 Reviews
  • All continental breakfasts and evening meals
  • Route notes and maps provided
Highlights of Gozo Cycling

Highlights of Gozo Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration6 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £909per person, tour only

  • 34 Reviews
  • All buffet breakfasts and evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Secrets of Sicily Walking

Secrets of Sicily Walking

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £938per person, tour only

  • 48 Reviews
  • All continental breakfasts and 3 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Marvels of Madeira Walk

Marvels of Madeira Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1069per person, tour only

  • 70 Reviews
  • All continental breakfasts, 2 picnics and all evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Secrets of Sicily Cycling

Secrets of Sicily Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration7 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1139per person, tour only

  • 15 Reviews
  • All continental breakfasts and 6 evening meals included
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Gozo Activities

Gozo Activities

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeMulti activity holiday
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £1159per person, tour only

  • 18 Reviews
  • All buffet breakfasts and evening meals included
  • Route notes and maps provided
  • Luggage transfers between hotels
Contrasts of Sardinia Walk

Contrasts of Sardinia Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £1238per person, tour only

  • 40 Reviews
  • All buffet breakfasts, 3 lunches and all evening meals
  • Led by experienced local guide
Amalfi to Sorrento Walk

Amalfi to Sorrento Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1329per person, tour only

  • 58 Reviews
  • All buffet breakfasts and 3 evening meals included
  • Route notes and maps provided
  • Luggage transfers between hotels
Islands of Sicily Walk

Islands of Sicily Walk

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!

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1349per person, tour only

  • 33 Reviews
  • All continental breakfasts
  • Route notes and maps provided
  • Luggage transfers between hotels
Exploring the Cinque Terre on foot

Exploring the Cinque Terre on foot

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration9 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1399per person, tour only

  • 28 Reviews
  • All buffet breakfast and 4 evening meals
  • Route notes and maps provided
  • Luggage transfers between hotels
Secrets of Tenerife Walk

Secrets of Tenerife Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1479per person, tour only

  • 34 Reviews
  • All buffet breakfasts, 5 lunches and all evening meals (including wine) included
  • Led by experienced local guide
Walking on La Palma

Walking on La Palma

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, twin centre
  • Activity level
  • Excellent for
  • From £1489per person, tour only

  • 12 Reviews
  • All buffet breakfasts, 5 lunches and all evening meals included
  • Led by experienced local guide
Walking on La Gomera

Walking on La Gomera

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeGuided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1519per person, tour only

  • 40 Reviews
  • All buffet breakfasts, 5 lunches and all evening meals (including wine).
  • Led by experienced local guide
Islands of Bermuda Walk

Islands of Bermuda Walk

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration7 nights, single centre
  • Activity level
  • Excellent for
  • From £1749per person, tour only

  • 26 Reviews
  • All buffet breakfasts and evening meals included
  • Route notes and maps provided
A Taste of Sicily Cycling

A Taste of Sicily Cycling

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided cycling
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £1799per person, tour only

  • 7 Reviews
  • All continental breakfasts and 6 evening meals
  • High quality bikes provided
  • Route notes and maps provided
  • Luggage transfers between hotels
Walking in the French Caribbean

Walking in the French Caribbean

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.

DEPARTURE MONTHS

JFMAMJJASOND

  • Holiday typeSelf-guided walking
  • Duration13 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From £2197per person, tour only

  • 5 Reviews
  • All continental breakfasts and 11 evening meals included
  • Route notes and maps provided
  • Luggage transfers between hotels