England Group Tours

The Cleveland Way

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A mixture of coastal and moorland walking The Cleveland Way. Walkers familiar with Wainwright’s Coast to Coast path will already be well acquainted with a couple of spots along the rolling Cleveland Way such as The Wainstones, Urra Moor and Robin Hood Bay. In fact it shares about 10 miles of routing with the ‘C to C’. Maybe they will be intrigued enough by their flirtation with the trail to don their boots once again and take up the challenge of the 110 mile Cleveland Way route from Helmsley to Filey in its entirety. What stands out is the experience of half a walk over hill and scarp edges and half along the hilly coastline of the Yorkshire seaside. There is much to enjoy for those interested in history, those ‘collecting’ National Trails and for aficionados who wish to enjoy arguably the best Fish ‘n’ Chips in England at Whitby Bay! This is the second of the ‘National Trails’, dating from 1969 and is rooted in the North York Moors National Park / Yorkshire Heritage Coast. Along its length there are contrasts in walking between field - quilted farmlands, forest patches, dramatic sandstone rock scarps, bleak moorlands and the highly eroded coastline, punctuated by beautiful little fishing villages, clinging to the cliffs. It is an area that has been threatened by the expansion of the Tyne – Tees Conurbation on the one side and by the encroaching North Sea on the other. However apart from busy coastal towns such as Scarborough, it remains a tranquil area, bolstered and protected by the presence of the National Park of which about 80% of the walk occupies. Highlights of the Cleveland Way include, the remains of the Norman Rievaulx Abbey, and 13th century Whitby Abbey (but dating from the 7th century!), the Captain Cook Monument and Robin Hoods Bay with it's cliff-hanging cottages. Most of the route follows well sign-posted footpaths, which generally have good surfaces and are easy to follow. The exception to this is along the coastal path, which, in some places, is overgrown and uneven underfoot. The amount of daily ascent and descent is moderate, with much of the walk being on level or gently sloping ground. There are a number of steep ascents along the section from Osmotherley to Urra Moor and at some places along the coast, but these are generally of no more than one or two hundred metres at a time.

Trekking and Hiking

Tour Type

Group Tour

Accommodation

Guest House, Hotel, Resort, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Filey, Helmsley, Scarborough, Os

Filey, Helmsley, Scarborough, Osmotherley, Clay Bank Top, Great Ayton, Saltburn, Whitby Bay, Robin Hood’s Bay

Duration12 days

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Coast to Coast: St Bees to Kirkby Stephen - 8 Days

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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.

Trekking and Hiking

Tour Type

Group Tour

Accommodation

Guest House, Hostel, Hotel, Hut, Resort

Age Range

18-99 yrs

Operated in

english

Destinations

London, St Bees, Ennerdale Bridg

London, St Bees, Ennerdale Bridge, Borrowdale, Grasmere, Glenridding, Shap, Kirkby Stephen

Duration8 days

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Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay

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Walk part of the Coast to Coast Walk through the Yorkshire Dales and North York Moors at your own pace. Embark on the eastern half of Alfred Wainwright’s legendary Coast to Coast walk, tracing the route from the rugged Pennines through the Yorkshire Dales and across the heather-covered North York Moors to the dramatic cliffs of the North Sea. Your hike begins near the halfway point of the trail in the Pennines Area of Outstanding Natural Beauty. Cross into the Yorkshire Dales National Park and climb the mystical Nine Standards Rigg. From there, you will follow the scenic River Swale past timeless villages and rolling farmland before arriving in the historic market town of Richmond. The journey continues into the North York Moors National Park, where panoramic vistas and sweeping moorland paths guide you towards the coast. The final stretch leads to Robin Hood’s Bay, where tradition calls for dipping your boots in the North Sea and marking your achievement with a pint, a glass of champagne, or an ice cream on the beach. Along the way, you’ll enjoy the charm of classic northern England; fields of sheep, rolling hills, dry stone walls, friendly local communities, and hearty full English breakfasts. Accommodation is in cosy country hotels, welcoming guesthouses, and traditional pubs—each reflecting the warm hospitality of rural England. For a gentler pace, our 11-day itinerary (trip code WCO) breaks up the final two long stages between Richmond and Blakey Ridge, giving you more time to savour the scenery. Scroll down to explore all our Coast to Coast walking holiday options.

Trekking and Hiking

Tour Type

Group Tour

Accommodation

Guest House, Hotel, Camping

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, Robin Hood’s Bay

Duration9 days

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England Group Tours

England Group Tours

Want a 100% customized small group tour itinerary to England?

182 Group Trips in England with 3,147 Reviews

European Discovery

European Trail

Romantic Britain & Ireland

The Cleveland Way

Coast to Coast: St Bees to Kirkby Stephen - 8 Days

The Cumbria Way - 8 Days

Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay - 11 Days

Scottish Islands Grand Tour - 14 days

South West Coast Path: St Ives to Mevagissey - 13 Days

Lake District From Edinburgh - 3 days

Coast to Coast: St Bees to Kirkby Stephen - 9 Days

South West Coast Path: Padstow to Penzance - 13 Days

South West Coast Path: Penzance to Mevagissey - 8 Days

Coast to Coast: Walk Kirkby Stephen to Robin Hood's Bay

182 Group Trips in England with 3,147 Reviews

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England Group Tours

England Group Tours

Want a 100% customized small group tour itinerary to England?

182 Group Trips in England with 3,147 Reviews

182 Group Trips in England with 3,147 Reviews