Best walks on the Isle of Wight

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Just off the south coast of England and only a 40-minute ferry ride from the mainland, the Isle of Wight does rather well when it comes to accolades. Not only has half the island been a designated Area of Outstanding Natural Beauty since 1963, but it also revels in its prestigious UNESCO Biosphere Reserve status awarded in 2019. As you’d expect, the walking opportunities here are worth shouting about, especially the Isle of Wight Coastal Footpath that takes you around the entire island. Here’s just a few of our favourite walking spots. 

Tennyson Down

This downland walk rewards with an amazing view of the Needles – the three iconic chalk stacks leading up to the Needles Lighthouse. The attractions here are plentiful, especially the Needles New Battery, and Needles Old Battery – all of which played a huge role in British history. You’ll get to follow in the footsteps of Poet Laureate Alfred Lord Tennyson, who once described the air here as so fresh it’s ‘worth sixpence a pint’. Don’t miss the clifftop walk to the Tennyson Monument, which stands on the highest point of the chalk cliffs of West Wight and dates from 1897. 


Far-reaching views of the downs and the English Channel are assured from Ventnor – the traditional seaside resort on the south of the Isle of Wight. Located beneath St Boniface Down (the highest point on the island), the town was once one of Britain's most famous Victorian health resorts due to its unique micro-climate (it gets more sunny days here than anywhere else). Must-dos here include relaxing at the sand and shingle beach, discovering Ventnor Botanic Gardens, and spotting ground-nesting birds like meadow pipit and skylark on Ventnor Downs. Also factor in a visit to Steephill Cove – arguably the island’s prettiest spot.

Compton Bay & Downs

Located on the coast road between Freshwater Bay and Brook, this two-mile-long bay attracts beachgoers, surfing fans, and those keen to soak up views of the cliffs at Freshwater. It’s also of huge interest to budding geologists and fossil hunters, not least for the large casts of dinosaur footprints that are visible year-round at low tide but best seen after a storm during the winter months. The wildlife-rich Compton Downs are also worth visiting for great walks, fantastic views, and rare species such as the orange and brown chequered Glanville fritillary butterfly which only survives on the undercliffs here and on the Channel Islands.


One of Queen Victoria’s most cherished spots, Shorwell charms with thatched cottages, three manor houses (Westcourt, Wolverton, and Northcourt), a good village pub, and plenty of history. Perfectly located for coastal strolls and lovely downland walks, the village has developed around St Peter’s church which was remodelled in 1440 with a tower and St Christopher mural. Spend your time wandering around the wooded area, making a wish as you cross the Shorwell Shute footbridge (currently closed for repairs), and taking advantage of some fabulous walking routes in all directions.


Located on a hill overlooking the village that bears its name, Carisbrooke Castle is a former artillery fortress, king's prison, and royal summer residence showcasing three unique building styles: Roman, Norman, and Elizabethan. Most revered as the spot Charles I was imprisoned prior to his execution in 1649, it’s ideal for climbing the steep steps to the mound for panoramic island views, enjoying the peaceful Princess Beatrice Garden, visiting the beautiful St Nicholas' chapel. and meeting Carisbrooke’s resident donkeys. 

3-night Isle of Wight Guided Walking

Accommodation: Freshwater Bay House, Freshwater

Departures: May-Nov 2023, 3 nights

Price from: £419pp

Book now or call 020 3974 8865

4-night Isle of Wight Self-guided Walking

Accommodation: Freshwater Bay House, Freshwater

Departures: May-Nov 2023, 4 nights

Price from: £575pp

Book now or call 020 3974 8865

7-night Isle of Wight Guided Walking

Accommodation: Freshwater Bay House, Freshwater

Departures: May-Nov 2023, 7 nights

Price from: £875pp

Book now or call 020 3974 8865

The Isle of Wight Coast Path Guided Trail

Accommodation: Freshwater Bay House, Freshwater

Departures: May-Sept 2023, 7 nights

Price from: £1,145pp

Book now or call 020 3974 8865