Trails & Island Hopping

Guided Trail Walking Breaks in the UK, Europe and Worldwide

Follow world-famous trails that take you along historic routes and past renowned landmarks - the perfect blend of challenging and inspirational. 

Walk long distance paths and classic trails or island hop across some of the finest scenery in Britain and around the world. 

You'll stay in carefully selected hotels and guesthouses where you can expect comfortable rooms, good food, and a friendly welcome. All our holidays are accompanied by an experienced leader and include luggage transfers and walks transport enabling day after day of carefree walking. 

At the end of your holiday you can look back and feel a huge sense of achievement at the journey you have completed on foot. So lace up those boots and begin your Trail Walking or Island Hopping adventure today!


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Enter dates, or leave the fields empty to see all availability
New

8 nights - From £1,359.00

An east to west coastal trek from Amalfi to Punta Campanella

  • Coastal

14 nights - From £1,979.00

Guided Trail

  • Meadows & hills
  • Rural peace
The Coast to Coast trail with HF Holidays

15 nights - From £2,049.00

Trek from the Irish Sea coast to the North Sea coast on one of Wainright’s most famous routes

  • Coastal
  • High Mountains
  • Hills & moorland

9 nights - From £1,724.00

Guided Island Hopping

  • Coastal
  • High Mountains
  • Hills & moorland

7 nights - From £1,300.00

Guided Island Hopping

  • Coastal
  • High Mountains

6 nights - From £849.00

Guided Trail

  • Hills & moorland
  • History

9 nights - From £1,275.00

Guided Trail

  • High Mountains
  • Hills & moorland

14 nights - From £2,399.00

An island hopping journey through the Azores' breathtaking volcanic terrain

  • Coastal
  • Hills & moorland
New

10 nights - From £1,949.00

Hike through stunning mountain scenery in this exciting traverse

  • High Mountains

10-11 nights - From £3,999.00

Incredible landscapes and extraordinary wildlife in Darwin's footsteps

  • Coastal
  • High Mountains
  • Stay longer
  • Wildlife
New

8 nights - From £1,400.00

A wild and varied adventure through this exciting Scottish Landscape

  • Coastal
  • High Mountains

7 nights - From £825.00

Guided Trail

  • Coastal
  • Flora
  • Hills & moorland
  • History

7 nights - From £1,369.00

Guided Island Hopping

  • Coastal

7 nights - From £1,069.00

Walk through medieval villages and past castles on this world-famous Pilgrim trail

  • Hills & moorland
  • History
  • Rural peace

6 nights - From £895.00

Guided Island Hopping

  • Coastal

7 nights - From £1,195.00

Island Hopping

  • Coastal
  • Hills & moorland

7 nights - From £1,195.00

Guided Trail

  • Hills & moorland

7 nights - From £1,095.00

Guided Trail

  • Coastal
  • Flora
  • Hills & moorland
  • Outdoors

7 nights - From £949.00

Guided Trail

  • Coastal
  • Hills & moorland
  • History
  • Wildlife

10 nights - From £1,899.00

Take on the challenge of Europe's most popular long-distance trail

  • High Mountains

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