The Isle of Wight is a world away from the bustle of the mainland. On our guided walking holidays you'll discover the best of the island’s glorious 85-mile coastline of unspoilt sandy beaches and dramatic white cliffs, as well as panoramic walks over the flower-rich chalk downland.
- Head out on guided walks with an experienced leader to discover the varied beauty of the Isle of Wight on foot.
- Admire panoramic views from dramatic cliff top coastal paths or along the lush Undercliff.
- Visit enchanting villages and beautiful unspoilt beaches.
- Look out for wildlife, find secret corners and learn about the Island's history
- A relaxed pace of discovery in a sociable group keen to get some fresh air away from the hustle and bustle of the mainland
- Evenings in our country house where you share a drink and re-live the day’s adventures
- High quality en-suite accommodation in our country house
- Full board from dinner upon arrival to breakfast on departure day
- 4 days guided walking; 1 free day
- Choice of up to three guided walks each walking day
- The services of HF Holidays Walking Leaders
- Any transport to and from the walks
On our Guided Walking holidays, we believe that choice is key. Our walks descriptions will help you choose according to your interests and fitness. The walks are grouped together with care by local experts to give the best experience. While every effort will be made to adhere to the described itinerary, we may occasionally vary the sequence shown here or substitute an alternative route to suit local conditions or for other operational reasons, potentially at short notice.
You're welcome to check-in to your room from 2:30 p.m. onwards (upgraded rooms from 1 p.m.) Please join us for afternoon tea.
Option 1 - Over Tennyson Down
Distance: 7 miles (11km)
Total ascent: 1,250 feet (380m)
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.
Option 2 - Headon Warren & Needles
Distance: 8½ miles (13.5km)
Ascent: 1,250 feet (380m)
In Summary: 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.
Option 3 - West Wight Circuit
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.
Option 1 - Through the Undercliff
Distance: 6 miles (10km)
Ascent: 600 feet (200m)
In Summary: Follow the coast along the Undercliff from St Catherine's Point to Ventnor’s Botanic Gardens.
Highlight: Walking through the lush vegetation of this natural suntrap
Option 2 - Godshill to Ventnor
Distance: 9 miles (14km)
Ascent: 1,300 feet (400m)
In Summary: Cross the downs from Godshill to Ventnor, passing the grand ruins of Appuldurcombe House and its surrounding parkland laid out by ‘Capability’ Brown.
Highlight: Enjoy great views right across the island from the top of Stenbury Down.
Option 3 - Woods & Downland
Distance: 10½ miles (16½km)
Ascent: 1,350 feet (420m)
In Summary: Walk through the woods near Sandown, then admire the widespread views as we cross the downs to Ventnor.
Highlight: Our path through Borthwood Copse and America Wood take us to one of the best places in England to spot Red Squirrels.
Option 1 - To Carisbrooke Castle
Distance: 6 miles (10km)
Ascent: 700 feet (210m)
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.
Option 2 - Shorwell & Carisbrooke
Distance: 9 miles (14km)
Ascent: 1,150 feet (360m)
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.
Option 3 - Tennyson Trail
Distance: 12½ miles (20½km)
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!
Option 1 - Calbourne to Freshwater
Distance: 6½ miles (10.5km)
Total ascent: 800 feet (240m)
In Summary: Walk from Calbourne to Freshwater Bay via the Downs.
Highlight: The much photographed 'chocolate box' cottages at Winkle Street in Calbourne. There's plenty of time to relax in the pool or gardens at the end of today's walk.
Option 2 - Mottistone Down
Distance: 8½ miles (14km)
Ascent: 1,100 feet (340m)
In Summary: From Winkle Street ascend over the Downs, descending Mottistone Down to the south coast. You then follow the coastal path back to Freshwater Bay.
Highlight: The final section over Compton Down enjoys splendid views over Freshwater Bay, and back along the island's southwest coast.
Option 3 - Hanover Point
Distance: 11 miles (17.5km)
Ascent: 1,250 feet (380m)
In Summary: Cross over the downs to Brighstone, then follow the coast path along the island’s southwest coast to Freshwater Bay.
Highlight: Tides permitting, look out for the fossilised forest at Hanover Point.
Enjoy a leisurely breakfast before making your way home.
Freshwater Bay House
Holidaying on the picturesque Isle of Wight doesn’t get any better than at Freshwater Bay House. Stood stop the island’s classic white cliffs and dominating the bay that it is named after, Freshwater Bay House has a gorgeous location. As well as 43 bedrooms, many decked out in blue and white printed wallpaper featuring foam-tipped waves breaking softly across the walls that act as a promise of the coastal scenery to come, there are three lounges and a friendly bar. Extensive gardens give on to the coast path, with a staircase that drops to the beach one way, while a path leads away across Tennyson Down towards the Needles in the other direction. If you’re experiencing some of the island’s plentiful sunshine (it averages around 2,000 hours a year), head to Alum Bay for coloured sands or Compton Bay for dinosaur footprints. Explore Carisbrooke Castle, stroll through Ventnor Botanic Gardens and keep an eye out for red squirrels in Borthwood Copse and America Wood.
Tea & coffee-making facilities, TV, Hairdryer, Toiletries, Wi-Fi
Stay in one of the main building’s bright, beautifully presented rooms, many that come with sea views. They’re mostly spacious and chic, styled to acknowledge the house’s nautical connections but with a modern twist of dove greys, clean whites and contemporary furniture. With 43 bedrooms, Freshwater Bay House has plenty of space and there’s a range of Good, Better and Best Rooms to choose from: Rooms 19 and 20 on the first floor come with spectacular sea views out over the English Channel; Rooms 18 and 22 are sumptuous corner rooms with expansive views over both the bay and Tennyson Downs. If it’s a room with a view you’re after, ask for Room 24, a superb, spacious corner space with five large windows all overlooking the gardens and bay, with its own private sitting room to relax in. Request Room 39 on the second floor and you’ll get an attractive corner room complete with a bath to soak in after a day of coastal walking.
All ‘Good’ rooms are ensuite and furnished to a high standard. There are also several ‘Better’ and ‘Best’ Rooms that are either larger or have a desirable view, a more luxurious mattress, larger television, enhanced toiletries and a fluffy bathrobe & slippers – upgrade your stay for just an extra £15-20 per person per night. You can choose a specific room for an extra £30 per room, subject to availability. Upgrade supplements still apply.
Free Wi-Fi, boot room and drying room, extensive garden, outdoor swimming pool, multi-purpose activity room, lounges, library and board games to borrow
After a day walking on the coast, come back to the house and its specially tailored walkers’ facilities. Relax by sitting in the extensive gardens or challenge a fellow guest to a game of croquet. If you’re visiting with children, turn them loose in the outdoor playground area or watch them splash in the large heated alfresco pool – there’s seating with sea views for you to enjoy a drink in too on a hot English summer’s day. For something less strenuous, snag a comfy chair in one of the three cosy lounges to read a book, play a board game or just hideaway; there’s a grand piano in one if you’re feeling musical. Head to the bar before dinner to perch on a tall stool with a perfect gin and tonic made with the Isle of Wight’s very own Mermaids Gin and a chance to catch up with your companions.
Food & Drink
As at all our country houses, holidays are full board, from afternoon tea served as a welcome treat through that evening’s meal to a hearty breakfast on the day of departure. Lunch is a chance to stock up on our famous picnic snacks. Food at Freshwater Bay House is hearty and has a strong emphasis on ingredients from the area and seasonal produce. Once a week the light-filled dining room hosts a Local Food Night, when, over a sociable evening, you might try a five-course feast of local flavours.
For accessibility and assistance information, please contact our expert team on 020 3974 8865
6 nights from 0pp
...or call 020 3974 8865