Cleveland Way Holiday

“Combine moor & coast, abbeys & smugglers villages in an orgy of history and beauty”

Holiday Enquiry Form
Preferred room type
Preferred daily mileage
Baggage movement service


The 108 mile Cleveland Way is an excellent way to enjoy the pleasures of a long distance walk. The contrasting scenery between moor and coast is interspersed with dabbles of history. This may be the architecture of Rievaulx and Whitby Abbey, the childhood of Captain Cook or the old industries of the 18th and 19th century.

Further Information on the Cleveland Way route

109 miles from Helmsley to Filey through the North York Moors and down the Yorkshire Coast.

Suggested Itinerary A (leisurely 10  days/11 nights)

Day 1: Helmsley to Sutton Bank (10 1/2 miles)

Day 2: Sutton Bank to Osmotherley (12 miles)

Day 3: Osmotherley to Clay Bank (11 miles)

Day 4: Clay Bank to Kildale/Great Ayton (9 miles)

Day 5: Kildale/Great Ayton to Saltburn (14.5 miles)

Day 6: Saltburn to Staithes  (9 miles)

Day 7: Staithes to Whitby (11.5 miles)

Day 8: Whitby to Robin Hood’s Bay (7 miles)

Day 9: Robin Hood’s Bay to Scarborough (15 miles)

Day 10 Scarborough to Filey (10 miles)

Suggested Itinerary B (speedy 7 days/8 nights)

Day 1: Helmsley to Osmotherley (22 miles)

Day 2: Osmotherley to Kildale (20 miles)

Day 3: Kildale to Saltburn (14.5 miles)

Day 4: Saltburn to Runswick Bay (12 miles)

Day 5: Runswick Bay to Robin Hood’s Bay (15 miles)

Day 6: Robin Hood’s Bay to Scarborough (14.5 miles)

Day 7: Scarborough to Filey (10 miles)

Your Cleveland Way Walking holiday includes

  • Advice on the route and the number of days suitable to you
  • An accommodation booking service
  • A guide book with detailed maps of the route.
  • Extra information on key route finding decisions, what to look out for (often short detours off the route)
  • A luggage movement service (optional)

You may have to be a little flexible on the start date due to the availability of accommodation. In some places (Sutton Bank and Chop Gate) it can be difficult getting 1 night stays over the weekend. Therefore we may have to change your start date by a day or so either side.

As a rule we do not book holidays for single travellers. It becomes very expensive as most accommodation do not offer reductions or single travellers.

We do accept parties with dogs (we have them ourselves) but it may limit the choice of accommodation.


There are no reviews yet.

Be the first to review “Cleveland Way Holiday”

Your email address will not be published. Required fields are marked *