I don’t know much about this adventure. But the weather is a worry.
… The walk from St Bees Head in Cumbria to Robin Hood’s Bay on Yorkshire’s east coast is now one of the most popular long-distance walks in Britain. At 178 miles (300km) long, the trail can be easily walked within a two-week holiday period. The route is based on permitted rights of way and minimises the amount of road walking. …
A Northern Coast to Coast Walk: From St Bees to Robin Hood’s Bay by Terry Marsh – Amazon
Consider also the Wainwrights pictorial guide and Stedman’s guidebook.
Walking Englishman – trip report




I recommend http://www.flickr.com/photos/garrulus/sets/72157605714100356/ (not mine) for pictures.