Guided Trails & Island Hopping Adventures

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 guest houses 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. 

By the end of your holiday, you’ll have achieved a huge sense of achievement so lace up and begin your trail or island hopping adventure!


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  • UK and Ireland
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Enter dates, or leave the fields empty to see all availability
New

14 nights - From £1,924.00

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

15 nights - From £1,940.00

Guided Trail

  • Coastal
  • Free WiFi
  • High Mountains
  • Hills & moorland

9 nights - From £1,194.00

Guided Trail

  • High Mountains
  • Hills & moorland
  • Wildlife

6 nights - From £774.00

Guided Trail

  • Hills & moorland
  • History

9 nights - From £1,624.00

Guided Island Hopping

  • Coastal
  • High Mountains
  • Hills & moorland
  • Wildlife

7 nights - From £1,224.00

Guided Island Hopping

  • Coastal
  • High Mountains
  • Wildlife

14 nights - From £2,399.00

Step through the island chain's volcanic terrain

  • Coastal
  • Flora
  • Hills & moorland

10-11 nights - From £3,815.00

IMMERSE YOURSELF IN THE WILDLIFE PARADISE

  • Coastal
  • High Mountains
  • Wildlife

6 nights - From £870.00

Guided Island Hopping

  • Coastal

7 nights - From £870.00

Guided Trail

  • Coastal
  • Hills & moorland
  • History
  • Wildlife
New

7 nights - From £1,000.00

Guided Trail

  • Coastal
  • Flora
  • Hills & moorland
  • Outdoors

7 nights - From £1,324.00

Guided Island Hopping

  • Coastal
  • History
  • Wildlife

7 nights - From £1,049.00

WALK THROUGH MEDIEVAL VILLAGES AND PAST CASTLES ON THIS WORLD-FAMOUS PILGRIM TRAIL

  • Hills & moorland
  • History
  • Rural peace
New

10 nights - From £1,219.00

  • Free WiFi
  • Hills & moorland
  • Value

7 nights - From £834.00

Guided Trail

  • Coastal
  • Flora
  • Hills & moorland
  • History

7 nights - From £1,124.00

Island Hopping

  • Coastal
  • Hills & moorland
  • History
  • Wildlife

7 nights - From £1,104.00

Guided Trail

  • High Mountains
  • History
  • Wildlife
New

7 nights - From £835.00

  • Coastal
  • Free WiFi
  • Hills & moorland
  • Value

7 nights - From £1,060.00

Guided Trail

  • Coastal
  • High Mountains
  • Wildlife
New

7 nights - From £735.00

  • Food & drink
  • Free WiFi
  • Hills & moorland
  • Value

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