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
Beautifully varied and wonderfully unspoilt, Dorset's award-winning Jurassic Coast offers 95 miles of idyllic sandy beaches backed by ancient craggy cliffs and meadows carpeted with seasonal wildflowers. In 2001, it gained UNESCO recognition as England's first Natural World Heritage Site charting 185 million years of the earth's history, with rocks and fossils dating to Triassic, Jurassic and Cretaceous times.
This 6-night Jurassic Coast walk is the perfect introduction to Dorset's wild and beautiful landscape, where the quietly rolling Purbeck Hills stand in stark contrast to the huge falcon patrolled chalk cliffs, and where every climb is rewarded with fantastic sweeping sea views. In the main, your route follows the coast-hugging long-distance South West Coast Path, pitching and swooping from one downland hollow to the next before a gentle descent into Lulworth Cove by way of the panoramic Burning Cliff and the world-famous rock-arch, Durdle Door. The 280-acre Durlston Country Park is a haven for wildlife (including rare red squirrels) and, with over 250 species of birds, is an ornithologist's paradise. On your final stretch of the Jurassic Coast walk, if you're lucky, you may spot bottlenose dolphins and playful seals emerging from the waves beyond Swanage where the procession of sculpted cliffs and towering chalk stacks known as Old Harry Rocks, marks the end of the Jurassic Coast.
As well as outstanding natural beauty, the region is also rich in archaeology with ancient forts and crumbling castles proudly guarding quintessential rural villages tucked into tranquil corners and crammed with traditional sandstone cottages, tempting tearooms and atmospheric old coaching inns serving great local food. The places you'll be staying in are among the best in the region, including a hotel with excellent leisure facilities and within walking distance of the Georgian Esplanade in Weymouth and a family-run property that looks out toward Swanage bay. Breakfasts are included everywhere; with so many dining options on your doorstep, we've left other meals up to you.
Trekking and HikingAdventure
Tour Type
Private Tour
Accommodation
Hotel
Age Range
8-99 yrs
Operated in
english
Destinations
Weymouth, Dorset, Isle Of Portla
Weymouth, Dorset, Isle Of Portland, Corfe Castle, Swanage
The Hadrian's wall trip was a perfect mix of hiking and touring the highlights of Northern England and the Lake District. Our guide Paul Cannon was very knowledgeable of the area being a native of the region. The places we stayed were inviting and comfortable.Overall the trip was all we expected and more.
Trekking and Hiking
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
Accommodation
Hotel
Age Range
16-99 yrs
Operated in
english
Destinations
Eden Valley, Newcastle, Alnwick
Eden Valley, Newcastle, Alnwick, Bamburgh, Keswick, London
Based in two centres, starting in Padstow then spending the second half of the week in Charlestown on the South coast. Our tour leader, Will, and his colleague Gaby, were prepared to go to any lengths to make sure we were fully supported. The walking required a decent level of fitness, the rating of 3 (moderate) is an accurate assessment, and my phone recorded 51 miles during the five days of walks (and 137,700 steps!).
The hotels were both good, although don't expect a sea view, and Will was always able to find us somewhere to eat despite COVID meaning there were a lot more tourists there than usual, and staffing was challenging for many of the restaurants.
The scenery is really lovely, both on the coast and inland, and lots of photos were taken and shared.
Trekking and HikingAdventure
Tour Type
Small Group TourSmall group tours usually have 8-12 participants and maximum up to 18 travelers
