4 Night Isle of Wight Guided Walking Holiday

Distance: 6 miles (9.5km)

Ascent: 700ft (220m)

In summary: Cross the island's central hills from the picturesque village of Shorwell to the impressive castle at Carisbrooke.

Highlight: Take time to explore this well-preserved castle. Walk around the walls, and watch the donkeys turn the treadmill to raise water from the well.

Distance: 9 miles (14km)

Ascent: 1,100 feet (340m)

In summary: Walk from the south coast to Shorwell village, then continue over the downs to Carisbrooke Castle.

Highlight: Explore picturesque Shorwell with its thatched cottages and historic church. There's also plenty of time to visit Carisbrooke Castle.

Distance: 12½ miles (20.5km)

Ascent: 1,600 feet (480m)  

In summary: Challenge yourself to this fantastic walk along the spine of the island from Carisbrooke Castle to Freshwater Bay. We’ll cross the hills to Shorwell then pick up the Tennyson Trail which runs along the top of the chalk downs. 

Highlight: This is one of our most popular walks. After several ups and downs, your celebratory pint at the end of the walk will be well deserved!

Distance: 6½ miles (10km)
Ascent: 600 feet (180m)
In Summary: A scenic walk along the coastal paths of the Isle of Wight as you walk from the historic Brading to Yaverland.
Highlight: Brading is home to the Church of St Mary. Although not mentioned in the Domesday Book, it is believed to be the oldest church and the most interesting on the island.

Distance: 8½ miles (14km)

Ascent: 700 feet (220m)

In summary: Soak up the sea air and as we follow the coastal path from the outskirts of Ryde to St Helens, then on over Culver Cliff to Sandown.

Highlight: The Yarborough Monument on top of Culver Down commands a wonderful view over the Solent and English Channel.

Distance: 11 miles (18km)

Ascent: 1,150 feet (360m)

In summary: Enjoy panoramic views on our walk from Havenstreet over Brading Down. We'll pass Bembridge Windmill and Culver Down, then along the coastal path to Sandown.

Highlight: Views over the Solent where vessels ranging from hovercraft to huge container ships complete this bustling scene.

Distance: 7 miles (11.5km)

Ascent: 900 feet (280m)

In summary: A gentle climb through the golf course on the Tennyson Trail to cross the Downs. The walk drops down to the farms around the Hamstead trail that lead to the south side of the island with some impressive views on the Coast Path that returns to Freshwater.

Highlight: Stunning panoramic views from 'The Downs', the site is famous for the Bronze Age burial mounds and endangered flora and fauna. 

Distance: 10 miles (16.5km)

Ascent: 1,250 feet (380m)

In summary: Traverse Compton and Brook Downs to ‘The Longstone’ before passing through the charming village of Mottistone and onto the South Coast path to return to the House.

Highlight: 'The Longstone' is a 10 ton 13 foot high megalith of iron sandstone of archaeological interest, plus the views from the coast path are spectacular.

Distance: 10.9 miles (17.5km)

Ascent: 1391 feet (424m)

In Summary: The route climbs the Tennyson Trail to the ridge of the island affording views of The Solent and English Channel. The walk passes the ancient Longstones and then through the village of Mottistone by the Manor owned by the National Trust. The return to Freshwater is by a combination of the Coast Path and rolling countryside.

Highlight: Discover the history of the Longstones, an external view of Mottistone Manor and panoramic views of the Downs and Coast.

Distance: 6 miles (9.5km)

Ascent: 700ft (220m)

In summary: Cross the island's central hills from the picturesque village of Shorwell to the impressive castle at Carisbrooke.

Highlight: Take time to explore this well-preserved castle. Walk around the walls, and watch the donkeys turn the treadmill to raise water from the well.

Distance: 9 miles (14km)

Ascent: 1,100 feet (340m)

In summary: Walk from Brightstone to the village of Shorwell village, then continue over the downs to Carisbrooke Castle.

Highlight: Explore picturesque Shorwell with its thatched cottages and historic church.

Distance: 12½ miles (20.5km)

Ascent: 1,600 feet (480m)  

In summary: Challenge yourself to this fantastic walk along the spine of the island from Carisbrooke Castle to Freshwater Bay. We’ll cross the hills to Shorwell then pick up the Tennyson Trail which runs along the top of the chalk downs. 

Highlight: This is one of our most popular walks. After several ups and downs, your celebratory pint at the end of the walk will be well deserved!

Distance: 6½ miles (10.5km)

Ascent: 740 feet (225m)

In summary: Experience coastal views from the most southerly point of the Island overlooking St Catherine’s lighthouse. Then continue along the coast to Steephill Cove and the sandy beach at Ventnor.

Highlight: Exploring the hidden gem, Steephill Cove, one of the prettiest beaches on the island.

Distance:  8 miles (13km) 

Ascent: 1,200 feet (370m)

In summary: Enjoy panoramic views from St Catherine's Down and visit the medieval lighthouse known locally as the Pepperpot. Then take in the sea views as we walk along the coastal path passing through picturesque Steephill Cove to the sandy beach of Ventnor.

Highlight: Explore the Victorian resort of Ventnor midway through the walk, and see the 11th Century St Boniface Church in nearby Bonchurch.

Distance: 10.5 miles (17km)

Ascent: 1,470 feet (450m)

In summary: This walk encompasses all the best bits of Option 2 but extends the journey inland to the charming village of Whitwell. We start at the village of Chale Green, ascend St Catherine's and head down and round St Catherine's Point. We'll continue to Whitwell and then rejoin the coastal path to Ventnor

Highlight: The cliff-top section above St Catherine's Point is particularly impressive, with views down to the lighthouse far below.

Distance: 7 miles (11km)

Ascent: 350 feet (120m)

In summary: Walk beside the tidal River Yar to the historic town of Yarmouth with its bustling harbour and Tudor castle. We’ll return on the opposite side of the river back to Freshwater Bay.

Highlight: The salt marsh, reedbeds and mud flats of the Yar Estuary are a great place to see wildfowl and waders.

Distance: 9 miles (14.5km)

Ascent: 550 feet (180m)

In summary: Walk through Golden Hill Country Park to the coast at Fort Victoria with uninterrupted views across the Solent to Hurst Castle on the mainland. Continue on the Coastal Path into the old port of Yarmouth and return to Freshwater beside the River Yar.

Highlight: A walk full of history from the Victorian forts at Golden Hill & Fort Victoria to the remains of Henry Vlll’s castle at Yarmouth.

Distance: 12 miles (19km)

Ascent: 800 feet (240m)

In summary: Enjoy the rolling countryside of the Hamstead trail, crossing the Island from south to north, before joining the Coastal path to the west of Hamstead.  The walk continues through Bouldnor Forest into the historic port of Yarmouth with its associated yachting activities. The return to Freshwater is by the River Yar and Afton Nature reserve.

Highlight: A variety of landscapes from the open countryside of the Hamstead trail to the beauty of Bouldnor Forest and the bustling little port of Yarmouth.  Opportunities to see wading birds by the River Yar.

Distance: 7 miles (11km)

Ascent: 1,200 feet (360m)

In summary: A fabulous walk over the chalk cliffs of Tennyson Down to the Needles and the Alum Bay; one of England's finest coastal walks.

Highlight: The commanding view over the Western Solent from the Tennyson Monument. You'll also discover the once secret rocket testing range, and the area's role in the space race.

Distance: 8½ miles (13.5km)

Ascent: 1,300 feet (400m)

In summary: We start by head to the coast at Totland Bay then soak up glorious sea view as you round the Needles headland and return over Tennyson Down.

Highlight: The heather-clad headland of Headon Warren is a real delight, and offers the best views of the Needles.

Distance: 12 miles (19km)

Total ascent: 1,550 feet (480m)

In summary: A circuit of the western tip of the island. We’ll follow the Yar Valley to Yarmouth, then follow the coastal path to Alum Bay, before a glorious finale over Tennyson Down.

Highlight: The final section atop the chalk cliffs of Tennyson Down is a fitting conclusion to this splendid walk.

Distance: 6½ miles (10.5km)

Ascent: 750 feet (240m)

In summary: Starting from Calbourne, the prettiest village on the island, we follow the footpath passing Winkle Street, and then ascending on to Westover Down before crossing countryside following the Tennyson Trail back to Freshwater Bay.

Highlight: Visiting the postcard village of Calbourne and enjoying breathtaking views of land and sea while walking along the Downs.

Distance: 8½ miles (13.5km)

Ascent: 1,300 feet (400m)

In summary: Walk from the charming village of Godshill onto the Stenbury and St Boniface Downs.

Highlight: The grand ruins of Appuldurcombe House and its surrounding parkland laid out by ‘Capability’ Brown.

Distance: 10½ miles (16.5km)

Ascent: 1,500 feet (460m)

In summary: Our 'eight Downs horseshoe' is a grand circuit that takes in the tops of Stenbury Down and St Boniface Down; the highest point on the island.

Highlight: Walking on top of the Downs is a real delight, with great views across the island, and across the Solent to the mainland.

Distance: 7 miles (11km)

Ascent: 350 feet (120m)

In summary: Walk beside the tidal River Yar to the historic town of Yarmouth with its bustling harbour and Tudor castle. We’ll return on the opposite side of the river back to Freshwater Bay.

Highlight: The salt marsh, reedbeds and mud flats of the Yar Estuary are a great place to see wildfowl and waders.

Distance: 9 miles (14.5km)

Ascent: 550 feet (180m)

In summary: Walk through Golden Hill Country Park to the coast at Fort Victoria with uninterrupted views across the Solent to Hurst Castle on the mainland. Continue on the Coastal Path into the old port of Yarmouth and return to Freshwater beside the River Yar.

Highlight: A walk full of history from the Victorian forts at Golden Hill & Fort Victoria to the remains of Henry Vlll’s castle at Yarmouth.

Distance: 12 miles (19km)

Ascent: 800 feet (240m)

In summary: Enjoy the rolling countryside of the Hamstead trail, crossing the Island from south to north, before joining the Coastal path to the west of Hamstead.  The walk continues through Bouldnor Forest into the historic port of Yarmouth with its associated yachting activities. The return to Freshwater is by the River Yar and Afton Nature reserve.

Highlight: A variety of landscapes from the open countryside of the Hamstead trail to the beauty of Bouldnor Forest and the bustling little port of Yarmouth.  Opportunities to see wading birds by the River Yar.