Cleveland Way: Holiday Packages

All our Standard Itineraries include:

    • Hand-picked accommodation in B&Bs/guest houses/inns/small hotels
    • En-suite facilities where available
    • Breakfast
    • Daily baggage transfers from our own team of local drivers
    • All booking fees

We will also endeavour to include all these in any custom itinerary you wish to build for this walk.

Itinerary A: 10 Days / 11 Nights

Day 1 – Helmsley to Kilburn (9.8m)
Day 2 – Kilburn to Osmotherley (13.9m)
Day 3 – Osmotherley to Clay Bank Top (10.8m) overnight in Great Broughton/Chop Gate
Day 4 – Clay Bank Top to Great Ayton (13.3m)
Day 5 – Great Ayton to Skelton (12.8m)
Day 6 – Skelton to Staithes (10.3m)
Day 7 – Staithes to Whitby (10.8m)
Day 8 – Whitby to Ravenscar (10.4m)
Day 9 – Ravenscar to Scarborough (North) (10.2m)
Day 10 – Scarborough to Filey (10.2m)

Standard Package Cost: £790 per person (based on two sharing)

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Itinerary B: 5 Days / 6 Nights

Day 1 – Helmsley to Osmotherley (19.1m)
Day 2 – Osmotherley to Great Ayton (24.2m)
Day 3 – Great Ayton to Staithes (23.7m)
Day 4 – Staithes to Robin Hoods Bay (18.2m)
Day 5 – Robin Hoods Bay to Filey Brigg (23.6m) or town (24.7m)

Standard Package Cost: £490 per person (based on two sharing)

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Itinerary C: 6 Days / 7 Nights

Day 1 – Helmsley to High Paradise (14.4m)
Day 2 – High Paradise to Clay Bank Top (17.9m)
Day 3 – Clay Bank Top to Slapewath (19.3m)
Day 4 – Slapewath to Runswick Bay (15.8m)
Day 5 – Runswick Bay to Ravenscar (18.3m)
Day 6 – Ravenscar to Filey Brigg (19.3m) or town (20.4m)

Standard Package Cost: £565 per person (based on two sharing)

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Itinerary D: 7 Days / 8 Nights

Day 1 – Helmsley to High Paradise (14.4m)
Day 2 – High Paradise to Clay Bank Top (17.9m)
Day 3 – Clay Bank Top to Newton under Roseberry (14.3m), leaving path at Roseberry Topping
Day 4 – Newton under Roseberry to Skinningrove (14.9m)
Day 5 – Skinningrove to Whitby (15.5m)
Day 6 – Whitby to Cloughton (16.5m)
Day 7 – Cloughton to Filey Brigg (14.8m) or town (15.9m)

Standard Package Cost: £595 per person (based on two sharing)

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Itinerary E: 8 Days / 9 Nights

Day 1 – Helmsley to High Paradise (14.4m)
Day 2 – High Paradise to Clay Bank Top (17.9m)
Day 3 – Clay Bank Top to Newton under Roseberry (14.3m), leaving path at Roseberry Topping
Day 4 – Newton under Roseberry to Saltburn (10.9m)
Day 5 – Saltburn to Runswick Bay (11.3m)
Day 6 – Runswick Bay to Robin Hoods Bay (14.8m)
Day 7 – Robin Hoods Bay to Scarborough (North) (13.7m)
Day 8 – Scarborough to Filey Brigg (10.2m) or town (11.3m)

Standard Package Cost: £665 per person (based on two sharing)

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Itinerary F: 9 Days / 10 Nights

Day 1 – Helmsley to High Paradise (14.4m)
Day 2 – High Paradise to Ingleby Cross (8.9m)
Day 3 – Ingleby Cross to Clay Bank Top (10.4m)
Day 4 – Clay Bank Top to Great Ayton, leaving the path at Cockshaw Hill (13.7m)
Day 5 – Great Ayton to Saltburn (13.9m)
Day 6 – Saltburn to Runswick Bay (11.3m)
Day 7 – Runswick Bay to Robin Hoods Bay (11.3m)
Day 8 – Robin Hoods Bay to Scarborough (North) (13.7m)
Day 9 – Scarborough to Filey Brigg (10.2m) or town (11.3m)

Standard Package Cost: £735 per person (based on two sharing)

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Itinerary G: 11 Days / 12 Nights

Day 1 – Helmsley to Kilburn (9.8m)
Day 2 – Kilburn to Osmotherley (13.9m)
Day 3 – Osmotherley to Clay Bank Top (10.8m)
Day 4 – Clay Bank Top to Kildale (9.8m)
Day 5 – Kildale to Slapewath (10.5m)
Day 6 – Slapewath to Skinningrove (8.2m)
Day 7 – Skinningrove to Runswick Bay (7.7m)
Day 8 – Runswick Bay to Whitby (7.9m)
Day 9 – Whitby to Ravenscar (10.4m)
Day 10 – Ravenscar to Scarborough (North) (10.2m)
Day 11 – Scarborough to Filey Brigg (10.2m) or town (11.3m)

Standard Package Cost: £855 per person (based on two sharing)

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Itinerary H: (Helmsley to Saltburn) (5 Days / 6 Nights)

Day 1 – Helmsley to High Paradise (14.4m)
Day 2 – High Paradise to Ingleby Cross (8.9m)
Day 3 – Ingleby Cross to Clay Bank Top (10.4m)
Day 4 – Clay Bank Top to Great Ayton, leaving the path at Cockshaw Hill (13.7m)
Day 5 – Great Ayton to Saltburn (13.9m)

Standard Package Cost: £445 per person (based on two sharing)

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Itinerary I: (Saltburn to Filey) (5 Days / 6 Nights)

Day 1 – Saltburn to Staithes (8.4m)
Day 2 – Staithes to Whitby (10.8m)
Day 3 – Whitby to Ravenscar (10.4m)
Day 4 – Ravenscar to Scarborough (North) (10.2m)
Day 5 – Scarborough to Filey Brigg (10.2m) or town (11.3m)

Standard Package Cost: £440 per person (based on two sharing)

Click here for a personal quote!