UK and Britain Solo Trips and Holidays 2025/2026

Step into the freedom of solo travel in UK and Britain. Traveling independently? Explore our collection of 300+ solo trips and holiday packages in UK and Britain, designed to connect you with like-minded adventurers.

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

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