Itinerary
- Day 1
Helmsley
Optional Activities
- Visit the ruins of the keep
- Browse local pubs, cafes and stores
Landmarks Helmsley Keep 
- Day 2
Helmsley to Boltby or Kilburn
- Meals
- Breakfast
Included Activities
- Walk through Rye Valley to Sutton Bank viewpoint
- Visit Rievaulx Abbey (12th century)
Optional Activities
- Return to Helmsley for the night (additional cost)
Landmarks Sutton Bank Rievaulx Abbey Kilburn White Horse - Day 3
Boltby or Kilburn to Osmotherley
- Meals
- Breakfast
Included Activities
- Walk along Hambleton Hills escarpment
- Follow Hambleton Cattle Drovers Road to Osmotherley
Landmarks Osmotherley - Day 4
Osmotherley to Great Broughton
- Meals
- Breakfast
Included Activities
- Climb over moors to Clay Bank Top
- Walk alongside Cringle Moor and Wainstones crags
Landmarks Clay Bank Top Cringle Moor Wainstones - Day 5
Great Broughton to Kildale
- Meals
- Breakfast
Included Activities
- Climb to Urra Moor and Round Hill (highest point at 454m)
- Walk along disused Ironstone railroad line
- Pass Captain Cook memorial
Landmarks Round Hill Kildale Captain Cook Memorial - Day 6
Saltburn-by-the-Sea
- Meals
- Breakfast
Included Activities
- Hike through forests with detour to Rosberry Topping
- Trek through moorlands and Guisborough forests
- Hike down to Slapewath ancient mineral mining area
- Coastal hike from Saltburn-by-the-Sea
Optional Activities
- Pub stop in Slapewath area
Landmarks Rosberry Topping Guisborough Forest Slapewath Saltburn-by-the-Sea - Day 7
Kildale to Whitby
- Meals
- Breakfast
Included Activities
- Walk along coastal cliffs to Rock Cliff viewpoint
- Visit Staithes fishing village
- Visit Runswick Bay
Optional Activities
- Travel to Whitby by bus (at own expense)
- Arrange return cab transfer to Whitby (at own expense)
Landmarks Boulby Cliff Staithes Runswick Bay - Day 8
Whitby
- Meals
- Breakfast
Included Activities
- Walk along coastal cliffs to Sandsend
- Walk into Whitby town
Optional Activities
- Visit Whitby Abbey ruins
- Follow Dracula Trail in town
- Enjoy fish and chips meal
Landmarks Whitby Abbey Whitby - Day 9
Whitby to Robin Hood Bay
- Meals
- Breakfast
Included Activities
- Climb 199 steps to abbey ruins and St. Mary's church
- Walk coastal cliffs to Robin Hood Bay
- Complete the Coast-to-Coast Trail
Optional Activities
- Visit Bay Hotel terrace
Landmarks Whitby Abbey St. Mary's Church Robin Hood Bay 
- Day 10
Robin Hood Bay to Scarborough
- Meals
- Breakfast
Included Activities
- Walk through Ravenscar abandoned resort
- Walk along coastal cliffs to Scarborough
Optional Activities
- Swimming
- Visit Scarborough castle ruins
- Enjoy ice cream and seaside activities
Landmarks Ravenscar Scarborough Castle 
- Day 11
Scarborough to Filey
- Meals
- Breakfast
Included Activities
- Walk along Cayton Sands
- Walk along cliffs to Filey Brigg
- Complete walk at Filey
Optional Activities
- Cross sands at low tide to Filey Brigg
Landmarks Filey Brigg Filey 
- Day 12
Filey
- Meals
- Breakfast
