Cleveland Way Walking Holiday

109 miles. Cleveland Way Walking Holiday.

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

To Cleveland Way is an excellent way to enjoy the pleasures of a long distance walk. Rarely does a walk cover nearly all there is to see in a specific area day after day. The itinerary below can be shortened or lengthened but is fairly typical for 108 miles.

The two itineraries detailed below are the most popular but you may wish to plan shorter or longer days, just ask our advice. Alternatively you may want to walk just part of the route and we can arrange that for you.

For more details on the Cleveland Way (and my personal account of the walk) refer to our Cleveland Way page

Cleveland Way map

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
  • 2 maps (O/S 1.25,000) with the route marked and alternatives suggested
  • Extra information on key route finding decisions, what to look out for (often short detours off the route)
  • Emergency contact details
  • A luggage movement service (optional)

Please contact us via the Enquiry Form or email for further details and prices. We will email you a sample itinerary and quote within 48 hours.

Booking enquiry form

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