Isle of Wight

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Walking holidays on the Isle of Wight

The Isle of Wight has earned its Area of Outstanding Natural Beauty status. Dramatic chalk-white cliffs look out over footprint-free beaches, and fleets of sailing yachts scoot merrily through the blue-green waters of the Solent.
Inland, cattle and sheep graze lazily in the fields, while winding hedge-fringed roads lead to thatched-roof villages where time seems to have stood still. If the mild climate and scenery weren’t enough, Isle of Wight walking holidays offer paths for all experience levels, outdoor activities galore, and enough heritage to fill a history book. 

And on an island that plays host to one of Britain’s biggest music events – the Isle of Wight Festival – you can expect plenty of entertainment in the pubs of pretty harbour towns like Cowes and Newport.  

Walk the Tennyson Trail  

Like gleaming shark teeth emerging from the surf, the Needles are one of the Isle of Wight’s most eye-catching attractions. They also mark a stop on the Tennyson Trail – a route made famous for being adored by British poet laureate, Alfred Lord Tennyson.  
From Tennyson Monument you can take in views that – on a clear day – encompass the entirety of the island. A stroll over the windswept grassy meadows of Tennyson Down provide a welcome break for tired legs, and the wooded sections of the Tennyson Trail are one of the best places in England to see native red squirrels.  

Other visit-worthy highlights along the 14-mile route include the poetry-inspiring panoramas from atop Brighstone Down, and the Needles Batteries – a pair of 19th century gun emplacements that served to protect Britain’s south coast during WWII and as a training ground for the D-Day landings. 

Uncover the island’s long and storied history  

The Isle of Wight music festival isn’t the only thing that makes itself heard here – the island’s history and heritage sing loud, too. Dinosaur fossils, battle-worn castles, ancient megalithic monuments, and a secret past as a base for Britain’s space programme – the island squeezes a lot into its small size.  

Follow in the footsteps of long-gone giants with a fossil hunt on the sands of Compton Bay and Yaverland, hear the myths and legends surrounding the 4,000-year-old Neolithic standing stone known as the Longstone, or visit the Renaissance-style Osborne House – the favourite royal residence of Queen Victoria.  

Elsewhere, Carisbrooke Castle stands as strong and sturdy as it did in its 17th century heyday when it held King Charles I prior to his execution in 1649. Walk the ramparts, peruse the museum or play bowls on the same green where the monarch passed time in the days leading up to his death.