Cleveland Way the full 109 miles/ 175 km
 
 

Starting at the North Yorkshire market Town of Helmsley and finishing in the small coastal Village of Filey. 
Itinerary for 8 to 11 nights below. 

Due to the rural nature of the walk there are times when it is not possible to find accommodation in walking distance from the path.  You will not be asked to walk any further than one and a half miles from the path to your accommodation, unless otherwise informed.  On the occasions where a (T) has been placed on the itinerary, a transfer from the path will be provided as part of your holiday.  This will either be provided by taxi service or by your host.  You will then be returned to the path the following morning to continue your walk.  When an (L) has been used, there is limited accommodation.  You may need a transfer at this location.  Further transfers not listed, may be required due to some accommodations having a two-night minimum booking policy or the accommodations close to the path being already fully booked.   This will be discussed with you at the time of booking your accommodation. 

If you have any questions, please contact us here at Embark walking holidays - we are happy to help.  

View over the North Yorkshire National park from Wainstones

CLEVW11 11 Nights, 10 Days

This route is classed as challenging

Holiday Code CLEVW11

11 Nights and 10 Days

Price per person ( based on two sharing) 

£1300.00

Arrival Day: Helmsley (Your start point)

    Walk Day 1: Helmsley to Sutton Bank (T)

    10 miles / 16 km

    Walk Day 2: (T) Sutton Bank to Osmotherley

    11.5 miles / 18.5 km

    Walk Day 3: Osmotherley to Clay Bank Top (T)

    11 miles / 18 km

    Walk Day 4: (T) Clay Bank Top to Roseberry Topping (L)

    14 miles / 22.5 km

    Walk Day 5: Roseberry Topping to Saltburn-by-the-Sea(L)

    10.5 miles / 16 km

    Walk Day 6: Saltburn-by-the-Sea to Staithes

    9 miles / 14.5 km

    Walk Day 7: Staithes to Whitby

    11.5 miles / 18.5 km

    Walk Day 8: Whitby to Robin Hoods Bay(L)

    6.5 miles / 10.5 km

    Walk Day 9: Robin Hoods Bay to Scarborough

    14 miles / 22.5 km

    Walk Day 10: Scarborough to Filey(L)

    11 miles / 18 km

    Departure Day: Filey (Your finish point)

High view over Staithes from the Cleveland Way

CLEVW10 10 Nights, 9 Days

This route is classed as challenging

Holiday Code CLEVW10

10 Nights and 9 Days

Price per person (based on two sharing)

£1210.00

 Arrival Day: Helmsley (Your start point)

    Walk Day 1: Helmsley to Sutton Bank (T)

    10 miles / 16 km

    Walk Day 2: (T) Sutton Bank to Osmotherley

    11.5 miles / 18.5 km

    Walk Day 3: Osmotherley to Clay Bank Top (T)

    11 miles / 18 km

    Walk Day 4: (T) Clay Bank Top to Roseberry Topping(L)

    14 miles / 22.5 km

    Walk Day 5: Roseberry Topping to Saltburn-by-the-Sea(L)

    10.5 miles / 17 km

    Walk Day 6: Saltburn-by-the-Sea to Runswick Bay(L)

    13 miles / 20 km

    Walk Day 7: Runswick Bay to Robin Hoods Bay(L)

    14 miles / 22.5 km

    Walk Day 8: Robin Hoods Bay to Scarborough

    14 miles / 22.5 km

    Walk Day 9: Scarborough to Filey(L)

    11 miles / 18 km

    Departure Day: Filey (Your finish point)

Wooden sign for Cleveland Way, pointing to Clay Bank

CLEVW9 9 nights, 8 Days

This route is classed as more challenging

Holiday Code CLEVW9

9 Nights and 8 Days

Price per person (based on two sharing)

£1080.00

Arrival Day: Helmsley (Your start point)

    Walk Day 1: Helmsley to Sutton Bank (T)

    10 miles / 16 km

    Walk Day 2: (T) Sutton Bank to Osmotherley

    11.5 miles / 18.5 km

    Walk Day 3: Osmotherley to Clay Bank Top (T)

    11 miles / 18 km

    Walk Day 4: Clay Bank Top to Roseberry Topping (L)

    14 miles / 22.5 km

    Walk Day 5: Roseberry Topping to Staithes

    19.5 miles / 31.5 km

    Walk Day 6: Staithes to Robin Hoods Bay(L)

    18 miles / 29 km

    Walk Day 7: Robin Hoods Bay to Scarborough

    14 miles / 22.5 km

    Walk Day 8: Scarborough to Filey(L)

    11 miles / 18 km

    Departure Day: Filey (Your finish point)

Woman walking the Cleveland Coast path along the coast line

CLEVW8 8 nights, 7 Days

This route is classed as more challenging

Holiday Code CLEVW8

8 Nights and 7 Days

Price per person (based on two sharing)

£970.00

Arrival Day: Helmsley (Your start point)

    Walk Day 1: Helmsley to Osmotherley

    21.5 miles / 34.5 km

    Walk Day 2: Osmotherley to Clay Bank Top (T)

    11 miles / 18 km

    Walk Day 3: (T) Clay Bank Top to Roseberry Topping (L)

    14 miles / 22.5 km

    Walk Day 4: Roseberry Topping to Staithes

    19.5 miles / 31.5 km

    Walk Day 5: Staithes to Robin Hoods Bay(L)

    18 miles / 29 km

    Walk Day 6: Robin Hoods Bay to Scarborough

    14 miles / 22.5 km

    Walk Day 7: Scarborough to Filey(L)

    11 miles / 18 km

    Departure Day: Filey (Your finish point)


 

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