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 Sutton Bank (10m)
Day 2 – Sutton Bank to Osmotherley (12m)
Day 3 – Osmotherley to Clay Bank Top (12m)
Day 4 – Clay Bank Top to Kildale (10m)
Day 5 – Kildale to Saltburn-by- Sea (15m)
Day 6 – Saltburn to Staithes (9m)
Day 7 – Staithes to Whitby (11m)
Day 8 – Whitby to Robin Hoods’ Bay (8m)
Day 9 – Robin Hoods’ Bay to Scarborough (14m)
Day 10 – Scarborough to Filey (10m)

Standard Package Cost: £780 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 (23.6m)

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

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Itinerary C: 6 Days / 7 Nights

Day 1: Helmsley to Osmotherley (19.1m)
Day 2: Osmotherley to Clay Bank Top (10.8m)
Day 3: Clay Bank Top to Newton under Roseberry (14.4m)
Day 4: Newton under Roseberry to Staithes (20.1m)
Day 5: Staithes to Robin Hoods Bay (18.2m)
Day 6: Robin Hoods Bay to Filey (23.6m)

Standard Package Cost: £555 per person (based on two sharing)

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Itinerary D: 7 Days / 8 Nights

Day 1: Helmsley to Osmotherley (19.1m)
Day 2: Osmotherley to Clay Bank Top (10.8m)
Day 3: Clay Bank Top to Great Ayton (13.3m)
Day 4: Great Ayton to Saltburn (15.2m)
Day 5: Saltburn to Sandsend (16.8m)
Day 6: Sandsend to Cloughton (20.2m)
Day 7: Cloughton to Filey (15.3m)

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

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Itinerary E: 8 Days / 9 Nights

Day 1: Helmsley to Osmotherley (19.1m)
Day 2: Osmotherley to Clay Bank Top (10.8m)
Day 3: Clay Bank Top to Great Ayton (13.3m)
Day 4: Great Ayton to Saltburn (15.2m)
Day 5: Saltburn to Runswick Bay (11.6m)
Day 6: Runswick Bay to Robin Hoods Bay (15.2m)
Day 7: Robin Hoods Bay to Scarborough (15.4m)
Day 8: Scarborough to Filey (8.2m)

Standard Package Cost: £660 per person (based on two sharing)

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Itinerary F: 9 Days / 10 Nights

Day 1: Helmsley to Boltby (12.6m)
Day 2: Boltby to Ingleby Cross (11.8m)
Day 3: Ingleby Cross to Clay Bank Top (11.1m)
Day 4: Clay Bank Top to Great Ayton (13.3m)
Day 5: Great Ayton to Saltburn (15.2m)
Day 6: Saltburn to Runswick Bay (11.6m)
Day 7: Runswick Bay to Robin Hoods Bay (15.2m)
Day 8: Robin Hoods Bay to Scarborough (15.4m)
Day 9: Scarborough to Filey (8.2m)

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 (9.9m)
Day 2: Kilburn to Osmotherley (14.2m)
Day 3: Osmotherley to Clay Bank Top (10.9m)
Day 4: Clay Bank Top to Great Ayton (13.3m)
Day 5: Great Ayton to Saltburn (15.2m)
Day 6: Saltburn to Staithes (8.6m)
Day 7: Staithes to Sandsend (8.2m)
Day 8: Sandsend to Robin Hoods Bay (10m)
Day 9: Robin Hoods Bay to Cloughton (10.3m)
Day 10: Cloughton to Scarborough (7.1m)
Day 11: Scarborough to Filey (8.2m)

Standard Package Cost: £798 per person (based on two sharing)

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

Day 1: Helmsley to Boltby (12.6m)
Day 2: Boltby to Ingleby Cross (11.8m)
Day 3: Ingleby Cross to Clay Bank Top (11.1m)
Day 4: Clay Bank Top to Great Ayton (13.3m)
Day 5: Great Ayton to Saltburn (15.2m)

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 (8.6m)
Day 2: Staithes to Whitby (11.2m)
Day 3: Whitby to Robin Hoods Bay (7m)
Day 4: Robin Hoods Bay to Scarborough (15.4m)
Day 5: Scarborough to Filey (8.2m)

Standard Package Cost: £430 per person (based on two sharing)

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