The first day is steep going, and has the bulk of the walking (22km). Start at Scarborough Castle, which skims the headland where Parliamentarians, Nazis and loose-bowelled seabirds have all laid siege. Scour for porpoises in the water, then cross town and join the Cleveland Way at North Bay Beach.
Thick gorse, dizzying cliffs and rugged pasture mark the first few kilometres, before descending to the cute beech-forested streams of Hayburn Wyke (rest up at the inn).
Then it’s all uphill until the ruins of Ravenscar Radar Station, part of a 1940s chain of defences that ringed the UK to warn of German attack.
Next up: Ravenscar, the town that never was. Recuperate with high tea at Raven Hall, then descend its cliff steps to see a colony of grey and common seals below (pups arrive in June, July & November), being sure to keep at least 10m distance.
Back on the trail, wind the ruined Peak Alum Works to Boggle Hole. At low tide you can walk the beach to the old fishing village of Robin Hood’s Bay. Finish with a Ghost Walk, listening to old smugglers’ tales and legends, before resting up.