Walking the Cleveland Way was a wonderful experience. The variety of countryside, moorland and coast, makes it extra special. The accommodation along the way was high quality with friendly hosts, and the luggage service worked like a dream. We met so many lovely walkers along the way and often dined with them in the evenings. It was such a
special trip.
Walking tours
Tour Type
Private Tour
Accommodation
Hotel, Resort, Villa, Guest House
Age Range
18-99 yrs
Operated in
english
Destinations
Filey, Helmsley, Scarborough, Os
Filey, Helmsley, Scarborough, Osmotherley, Clay Bank Top, Great Ayton, Saltburn, Runswick Bay, Whitby Bay, Robin Hoods Bay
Follow the Coast to Coast Walk from St Bees towards the historic villages and beautiful landscapes of the Yorkshire Dales. Experience the most dramatic section of Wainwright’s legendary Coast to Coast route on this self-guided walking holiday from the Irish Sea at St Bees to the market town of Kirkby Stephen. The western half of the trail showcases some of the most spectacular scenery in northern England, taking you across the rugged heart of the Lake District National Park and into the edge of the Yorkshire Dales.
If you're short on time, new to long-distance walking, or prefer to explore the route in manageable stages, this itinerary is an ideal way to sample the best-loved landscapes of the Coast to Coast. It’s also perfect for hikers who simply want the thrill of crossing the Lake District on foot, experiencing the quiet valleys, shimmering lakes, towering peaks and traditional fellside villages. You’ll start your journey by dipping your boots in the Irish Sea at St Bees, then head east with the prevailing wind at your back. The route leads through dramatic valleys such as Ennerdale, Borrowdale, and Patterdale, with the chance to take optional high-level detours to iconic Lakeland summits like Helvellyn. As the Lake District fells give way to the gentler landscapes of the Yorkshire Dales, your walk concludes in Kirkby Stephen, a charming town with rail links and a great place to relax after an inspiring week on the trail.
Looking to take things at a gentler pace? Our 9-day version of this trip (trip code WSK) breaks up the longer stage between Shap and Kirkby Stephen, offering a more relaxed alternative.
Scroll down to explore all our Coast to Coast walking options.
Walking tours
Tour Type
Private Tour
Accommodation
Hotel, Hut, Hostel, Guest House, Resort
Age Range
18-99 yrs
Operated in
english
Destinations
St Bees, Kirkby Stephen, Ennerda
St Bees, Kirkby Stephen, Ennerdale Bridge, Borrowdale, Grasmere, Glenridding, Shap
Great walk, beautiful scenery, excellent accommodation, luggage transfers went without a hitch. Electronic map made it almost impossible to get lost. English weather!
I had a very well planned and arranged trip on the East Coast to Coast from Kirkby Stephen to Robin Hood's Bay. The accommodations arranged were comfortable, friendly, and well situated along the trail. The bag transport worked very well, as did the return transfer to Kirkby Stephen where my car was waiting. The advice on dining was right on and the maps, instructions, and attractions along the way were super. Well done!
Walking tours
Tour Type
Private Tour
Accommodation
Hotel, Guest House
Age Range
18-99 yrs
Operated in
english
Destinations
Robin Hoods Bay, Kirkby Stephen
Robin Hoods Bay, Kirkby Stephen, Keld, Reeth, Richmond, Osmotherley, Blakey, Egton Bridge
An amazing walking holiday across stunning scenery in the Lakes District. Very well supported by the team, with delightful accommodation, good maps and luggage handling. Thank you!
We loved how quiet and well marked the trails were, along with the detailed trail descriptions provided. The small towns we visited were an unexpected treat as well. For a coastal walk, there was an amazing amount of variety from cliffs, to beach, and through fields. The ability to easily take a bus or tram from place to place if desired, was an added benefit. The accommodations were nice (especially those rooms with a sea side view!) and the people friendly.
Trekking and Hiking
Tour Type
Private Tour
Accommodation
Hotel, Resort
Age Range
18-99 yrs
Operated in
english
Destinations
Isle Of Man, Douglas, Castletown
Isle Of Man, Douglas, Castletown , Port Erin, Peel , Jurby , Ramsey , Laxey
