Walking Holidays and Outdoor Adventures on the Isle of Wight

Coastal Paths, Chalk Downs, and Seaside Villages

Where cliffs and coves frame a compact island made for walking.

The Isle of Wight, just off the south coast of Hampshire, is a county in its own right and one of England’s most popular destinations for walking holidays and outdoor adventures. Compact yet diverse, the island offers chalk downs, rolling farmland, ancient woodland, and more than 60 miles of dramatic coastline. The Isle of Wight Coast Path circles the island, while inland trails like the Tennyson Trail link viewpoints, ridges, and historic landmarks.

Walking here might mean climbing to Tennyson Down for sweeping sea views, exploring seaside towns such as Shanklin and Ventnor, or discovering the Needles on the island’s western tip. With ferry links from Portsmouth, Southampton, and Lymington, the Isle of Wight is an easy-to-reach escape for both weekend breaks and longer self-guided walking holidays.

Trails Through the Isle of Wight

Isle of Wight Coast Path
A 70-mile National Trail (in development) around the island, linking beaches, cliffs, and seaside towns.

Tennyson Trail
A ridge walk from Carisbrooke Castle to the Needles, crossing chalk downs with wide views of land and sea.

St Boniface Down Walks
Routes around the island’s highest point near Ventnor, with heathland, wildflowers, and coastal panoramas.

Bembridge and Culver Down
A circular walk around Bembridge Harbour and Culver Cliffs, mixing seaside scenery with historic fortifications.

Adventure Highlights

• The Isle of Wight Coast Path — a complete island circuit
• Iconic coastal landmarks: the Needles and Culver Down
• Ridge walks over Tennyson Down and St Boniface Down
• Seaside towns and walking hubs: Shanklin, Ventnor, and Yarmouth
• Festivals, heritage sites, and car-free exploration with local buses and ferries