Walks on the Isle of Wight - 5 of the Best

Stepping ashore on the Isle of Wight feels like landing in a part of England where time has shifted ever so slightly backwards to a point where life was less frenetic. The largest island in England naturally has a long coastline, much of which is lined with coastal paths so that walkers can make the most of the scenery.

Unspoilt sandy beaches are interspersed with sections of white chalk cliff-face which lead to large areas of chalk down. Inland, wooded areas are home to red squirrels, separated from the dominant greys by the protective waters of the Solent. Stroll across landscapes where dinosaurs once roamed and soak up the charming island life. 

OUR TOP 5 WALKING ROUTES on the Isle of Wight

All of these routes are available on our guided and self-guided walking holidays on the Isle of Wight. Other routes available; choose from three walks each day of different grade for maximum flexibility and choice.

Skip down to discover each walk

1. Through the Undercliff  2. West Wight Circuit  3. Yar Valley
4. Chale Green to Shanklin  5. Tennyson Trail 

1. Through the Undercliff

Distance: 6 miles (10km)
Total ascent: 600 ft (200m)
Estimated walking time: 3 hours

The walk in a nutshell: An easy, gently undulating walk on the south of the island taking in parts of the Undercliff and ending at Ventnor’s splendid Botanic Gardens.

Don't miss: Wandering through the different zones of the Botanical Garden to enjoy the splendour of exotic vegetation.


The walk starts at Gore Down from where an octagonal tower can be seen – the only part of the 14th Century St. Catherine’s Oratory that is still standing. It is the only surviving medieval lighthouse in England.

The route heads south to reach the coast path at Gore Cliff from where it heads east over St. Catherine’s Point towards the town of Niton. There are splendid views of the cliffs to the right; signs of landslips are very evident; the sandy ground is under constant attack from the elements.

At Niton we head inland, following the Yar River Trail – Niton has a spring which is the source of the River Yar. The path continues to the village of Whitwell – home of The White Horse Inn – the oldest pub on the island. From here we head south once again, back to the coast at St. Lawrence to join the path along the Undercliff. The area was popular in Victorian times and many of the larger houses here date back to this time. Passing through Steephill Cove – an unspoilt, car-free, traditional fishing village – the walk ends at the Botanic Gardens in Ventnor.

The gardens were founded in 1970 by Sir Harold Hillier and benefit from their sheltered, sunny position. The warm micro-climate here allows exotic sub-tropical plants to thrive. The garden is set out into different geographical zones and includes a humid tropical house, cacti and succulents and a New Zealand garden. Look out for wall lizards in the Mediterranean garden.

2. West Wight Circuit

Distance: 12 miles (19km)
Total ascent: 1,550 ft (480m)
Estimated walking time: 5 hours 50 minutes

The walk in a nutshell: A splendid circular walk to and from the doorstep of our accommodation in Freshwater Bay which takes in the western tip of the island.

Don't miss: Standing on the cliff-tops over-looking the colourful sand cliffs at Alum Bay and the chalk sea stacks which make up The Needles.


Setting off eastwards around the bay, we join the Freshwater Way northwards and along the causeway to cross the River Yar. The route then follows the Yar Valley all the way to the historic harbour town of Yarmouth.

From here, the route heads west along the coast path through Fort Victoria Country Park and past Cliff End Battery and Fort Albert which date back to the late 1800s. The path heads inland before swinging back to the coast at the far end of Colwell Bay from where there are stunning views across the Solent to Hurst Castle on the mainland.

The path straddles the coast heading south-west around the town of Freshwater and then on to Headon Warren where the path provides a good view of a large stretch of land which is gradually sliding away into the sea. Almost on the western tip of the island is Alum Bay whose main claim to fame is the many-coloured sands which make up the crumbling cliffs. A small cable car gives visitors a bird’s-eye view of the land below.

A short climb brings you to West High Down for aerial views of The Needles – the Isle of Wight’s famous sea stacks which are all that remains above water of a limestone outcrop which used to connect the Wight to the mainland in Dorset. The lighthouse here warns shipping of the treacherous rocks but even so, many vessels have foundered here including the SS Varvassi whose barely submerged funnel now forms a hazard all of its own.

The grand finale of the walk is across Tennyson Down past the Tennyson Monument – a tribute to the Victorian poet laureate who used to live nearby and enjoyed walking across the downs. From here there are sweeping views towards Compton Bay and across Freshwater. A short walk downwards take us back to Freshwater Bay House for some well-earned refreshments.

3. Yar Valley

Distance: 7 miles (11km)
Total ascent: 350 ft (120m)
Estimated walking time: 3 hours 50 minutes

The walk in a nutshell: An easier circular walk taking in both sides of the Yar Valley which starts and ends from the doorstep of our accommodation in Freshwater Bay. Much of the route is flat and on well-surfaced paths.

Don't miss: The wildfowl which inhabit the saltmarsh and reedbeds of the Yar estuary. You may also be able to find some tasty samphire to nibble on!


We start off walking eastwards around Freshwater Bay before heading upwards for a short distance to join the Freshwater Way across the fields to Afton Farm. Here the path briefly follows a quiet road before we strike out in a north-easterly direction to follow the path of the River Yar. The entire river valley falls within an Area of Outstanding Natural Beauty. 

The upper reaches of this short tidal river contain a landscape of mud flats, saltmarsh and reedbeds. These varied habitats support a wide range of water birds. Look out for species including dunlin, redshank, curlew, black-tailed godwit, shelduck, wigeon, oystercatcher and little egret. You may also spot the glossy spikes of samphire (also known as glasswort) growing out of the mud – a salty delicacy in many restaurants!

The path passes through some wooded areas – look out for the red squirrels who live here – before reaching the historic harbour town of Yarmouth. There has been a settlement here since about 991! Look out for the Tudor castle and wooden pier – reputed to be the longest wooden pier in the country that is still open to the public.

Crossing the River Yar via the town’s bridge, it’s a short walk to the Freshwater Way which heads south along the opposite side of the valley. We return to Freshwater Causeway but take an alternative path back through Freshwater past Afton Marsh SSSI which is home to water voles – one of Britain’s most endangered species. It’s then a short stretch back to Freshwater Bay House.

4. Chale Green to Shanklin

Distance: 11.5 miles (19km)
Total ascent: 1,750 feet (540m)
Estimated walking time: 5 hours 45 minutes

The walk in a nutshell: A linear walk on the Isle of Wight’s picturesque south coast from Whale Chine to Shanklin.

Don't miss: The many ‘chines’ along the way. Chine is the local word used to describe narrow, water-filled ravines which lead to the sea.


The walk starts from the car park at Whale Chine – a narrow ravine which has been cut into the sandstone cliffs by a small stream. You will be following in the footsteps of dinosaurs – many fossil bones have been found in these cliffs.

After a short stretch along the road, the path descends down to the coast at Walpen Chine for excellent views towards the headland at St. Catherine’s Point. The route meanders a little to avoid sections where the path has slid towards the sea – the sandy cliffs are somewhat unstable. 

Reaching the headland there are impressive views down to St. Catherine’s Lighthouse – the most southerly tip of the island. From here the coastal path heads inland a little towards the town of Niton before striking east to St. Lawrence where it once again descends to reach and follow The Undercliff headed for Ventnor. This seaside town grew rapidly in Victorian times when it became a popular holiday destination due to its sheltered position, beautiful outlook and the promotion of the health benefits of its warm climate and waters. Much of the Victorian architecture remains intact today giving the town an old-world charm. 

At Bonchurch the route rounds the corner of the island to head north-east. The path then passes through a wooded area known as ‘The Landslip’ which has been a popular woodland walk since Victorian times. Look out for the moss-covered boulder next to the path known as The Wishing Seat. Tradition has it that if you sit on the Wishing Seat, and make a wish, it will come true.

The route continues through the tiny village of Luccombe before reaching the end point in the seaside resort of Shanklin – a great place to enjoy an ice-cream or cooling drink. 

5. Tennyson Trail

Distance: 12.5 miles (20.5km)
Total ascent: 1,600 ft (480m)
Estimated walking time: 4 hours 35 minutes

The walk in a nutshell: A leg-stretching walk from the centre of the island culminating in a gentle descent over Compton Down back to Freshwater Bay at the coast.

Don't miss: Admiring the imposing ramparts of Carisbrooke Castle and seeing them recede as we head off across the chalk downs.


The start point is Carisbrooke Castle just outside the island’s county town of Newport. This is also the site of a Roman Fort but the castle was built during the Norman Conquest. This remarkably intact castle was famously used to imprison King Charles 1 for a year before he was tried and executed during the Civil War.

The route heads south upwards along the Shepherd’s Trail over chalk hills with elevated views across the island. Leaving the Shepherd’s Trail we head west over Garston’s Down before dipping south atop the hills passing a TV mast. Heading in a north-westerly direction, we take a detour through the pretty village of Shorwell. The village is said to have been a favourite of Queen Victoria’s with its pretty thatched cottages and stream running down the centre. The village has a 12th century church, a traditional country pub and village shop.

An uphill section leads to Limerstone Down. From the viewpoint here the rolling downs stretch out in all directions towards the white cliffs at Freshwater. From here, the route runs along the top of the chalk downs for several miles with glorious panoramic views in all directions. Closer to Freshwater Bay we pick up the Tennyson Trail which takes us over Compton Down and back to Freshwater Bay House where we can sit back and reflect on a rewarding walk.

Isle of Wight Walking Holiday Options 

All of our guided and self-guided walking holidays on the Isle of Wight stay at our own accommodation - Freshwater Bay House - right on the coast.

Guided Walking Holidays
on the Isle of Wight
Self-Guided Walking
on the Isle of Wight
Family Walking Holidays
on the Isle of Wight