Best walks on the Isle of Wight holiday cottages

Best walks on the Isle of Wight

Ed 01 April 2019

The Isle of Wight is home to an amazing choice of rural and coastal trails. The longest of all is the 67-mile long Coastal Path which takes between four and seven days to complete. There are some exceptionally beautiful, scenic stretches of the path, particularly along the wild open stretches at the south of the island between Blackgang Chine and Yarmouth.

From Victorian esplanades and promenades, to cliff top trails, sunken roads and hollow ways, farm tracks, deep coves, elevated hill top meanders; the Isle of Wight is a microcosm of many of the elements that make holidays in the British countryside so fantastic. 

A walk beside a tidal creek on the Isle of Wight

Its variety of wildlife and habitats draws in a magnitude of tourers annually to this ever up and coming holiday destination for trekkers and pleasure walkers. From the northern shore you can look back at the mainland across the Solent taking in the estuary of the Beaulieu River and Lymington Harbour, Hurst Castle peninsula in the west, Southampton Water, Portsmouth and Calshot Spit in the east.

The Isle of Wight has inspired painters and authors for hundreds of years, it’s land mass has also been fought over with the French throughout the Napoleonic era and earlier. Coming under siege rather frequently, hence the ring of hefty fortresses all around the island and off-shore. Charles Dickens is said to have written parts of David Copperfield at Bonchurch – other greats include Alfred Lord Tennyson who has a walk named after him, and Algernon Charles Swinburne.

This guide is sure to inspire you to explore some of the diverse and fantastic island walks.

Tennyson Down Circular

  • 7 miles – moderate - Tennyson Down Car Park (nr Totland), via Freshwater and Alum Bay

The former Poet Laureate, Alfred Lord Tennyson walked these downs seeking inspiration for his prose. Nowadays there is an utterly spellbinding walk that takes in the magnificent chalk cliff faces of the western island, the Tennyson Memorial Cross, Scratchell Bay, The Needles with their preposterously perched lighthouse, sea bird roosts, wild grass tracts offering shelter for butterflies that hide from the thermals - you may catch sightings of Adonis blues, chalk hill blues, and dark green fritillaries. Orchid fans will already know there can be up to nine species found in this rich chalk grassland area of the island. Make sure you take in the Old and New Batteries – one-time fortresses – the former was built to ward off French invasions in the mid-1800s. The latter was built as a base for a rocket test site in the 1950s.

tennyson cross

The walk can be divided into two circuits if you decide to cut back to the car park from the Tennyson Monument. The sea and cliff views on this trail are exceptional and you will be in no doubt as to why one of our most treasured poets came to this end of the Isle of Wight during his lifetime.

Preparation – Explorer OS Map OL16; dog waste bags (if appropriate), drinking water on a hot day (no shade).

Stay at Moonfleet Cottage - Freshwater Bay


This charming cottage is beautifully sited on the cliff top above Freshwater Bay in an Area of Outstanding Natural Beauty. There are spectacular sea views of the bay and South coast from the cottage and garden, as well as fine views of Tennyson Down.

Brighstone to Niton

  • 8 miles – moderate

This coastal leg-stretch runs parallel to one of the best driving roads in Europe, the Military Road, which cuts along one of the best swathes of unspoilt coastline on the Isle of Wight. With a bold sunset the view westwards at the close of a day is transportive and reminiscent of far away lands in the Southern Hemisphere. Fairly level for the most part with a long gradual ascent/descent at the Blackgang Chine, where there is a fun theme park, the end of the trail in the east near Niton.  

miltary road

The land’s edge is punctuated by a series of narrow gullies known as chines - be sure to register the craggy Whale Chine which is, arguably, the most impressive. Also keep your eyes peeled for the Pepper Pot/St Catherine’s Oratory, which is the remains of a medieval lighthouse, and the Salt Cellar, an unfinished 18th century lighthouse on St Catherine’s Hill.

Preparation – Explorer OS Map OL16; dog waste bags (if appropriate), drinking water on a hot day (no shade).

Stay at Driftwood Cottage - Brighstone

This attractive cottage situated on a small complex of similar holiday properties, sleeping up to seven guests, is located in the coastal village of Brighstone on the Isle of Wight’s south coast. With breath-taking views of the Downs and the coast to be enjoyed from the property and the garden it's a beautiful home from home on the Isle of Wight.

Cowes to Yarmouth

  • 16 miles - challenging

Two thirds of this north island trail are along the coast, the remainder cuts inland through the Hamstead Heritage Coast avoiding the Newtown River and Clamerkin Brook incursions. Start at either end in the west or east and the path takes you through bucolic farmland, wild copses and meadows, beaches and an esplanade with views across the Solent to the mainland, a yachting playground.

cowes weeks

Highlights include the lesser known medieval inland port of Newtown, Egypt Esplanade which is punctuated by its lion adorned cenotaph, and the chain ferry that connects Cowes to East Cowes. Hilly in some of the westerly sections of the trail variety and the 16-mile length of the trail makes this a challenge – however, there is plenty of cover from the sun and places to stop and eat along the route at Cowes, Newtown, Thorness Bay (Parkdean) and Yarmouth itself.

Preparation – Explorer OS Map OL16; dog waste bags (if appropriate).

Bembridge to Shide Trail

  • 11 miles – moderate – Shide (near Newport) to Bembridge

This trail begins/ends at the east coast town of Bembridge which is known for its tidal nature reserve and iconic lifeboat station with pier. Its course also runs over Culver Down, Arreton, Brading Downs, and the town of Brading. Views across the former and Sandown are well worth climbing for. Brading is one of the island’s oldest settlements and it is home to a Roman Villa, and some very pleasant village pubs for a pitstop.

bembridge pier

It also has a restored railway station with signal box and a café. It is connected to Shanklin and Ryde on the Island Line. Habitats include chalk grasslands, downs, woodlands, marshes, hills and meadowlands. The opposite end of the trail starts/ends at the Barley Mow Pub in Shide, just a short distance from the centre of Newport.  Newport is well connected with other towns via public transport for the return trip.

Preparation – Explorer OS Map OL16; dog waste bags (if appropriate).

Stay at Driftwood Cottage at Forelands


Driftwood Cottage is a lovely detached property in the coastal area of Forelands in Bembridge, on the east coast of the Isle of Wight. It is attractively situated within a 1 minute walk of the sea and overlooks a private grassy area which provides access to this quiet area of beach and some parking. 

Niton to Sandown

  • 9 miles – moderate

This trail runs between the east coast seaside resort of Sandown with its broad sands and pier, and the south-island village of Niton. Taking in contrasting coastline habitats, the walk encompasses tall cliffs, tropical flora, the botanical gardens at Ventnor, Bonchurch and the popular Shanklin. The southern end of the beach leads past the entrance to the landscaped gardens of Shanklin Chine. The cliffs tower above this end to the beach as it peters out. Around the headland is the diminutive Luccombe Beach.

st catherines lighthouse

The trail passes through the quaint village of Bonchurch on the northern outskirts of Ventnor. At low tide, families come to play and explore the rockpools.  The village has several cafes offering light lunches and refreshments. Throughout the years, Bonchurch has been an inspiration to authors and artists. Charles Dickens is said to have written parts of David Copperfield during one of his visits.

Ventnor is also a great destination and the beach is a very pleasant place to take a break on your trek. Ventnor’s seafront still retains a Victorian flavour and has a ton of character. Facing south into the openness of the English Channel this bright beach is a joy to spend time at. Look out for red squirrels along the wooded stretch of cliff top trail around the St Lawrence and St Catherine’s Lighthouse area. This is a great walk to get a flavour of the most popular parts of the island and the countryside that falls between the towns.

Preparation – Explorer OS Map OL16; dog waste bags (if appropriate).

Stay at The Wing - Puckaster House

Stay in a wing of this gorgeous ‘Cottage Ornee’ style house, which boasts several acres of garden and lawns. Ideally situated on the southern tip of the Isle of Wight, this enchanting haven is ideal for exploring the island or escaping from it all.

Map of walking trails

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Walking holidays on the Isle of Wight

We have a selection of hand-picked holiday homes close to all the walking trails on the Isle of Wight - check out our collection of Isle of Wight cottages for inspiration. Whatever kind of holiday you're looking for, you'll find the perfect place to stay among our range of accommodation.

Disclaimer: Whilst every effort has been made to ensure the accuracy of the information at the time of writing, please ensure you check carefully before making any decisions based on the contents within this article.

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