6-Night Isle of Wight Guided Walking Holiday

Freshwater Bay - IOW
Duration: 6 nights
Type: Guided Walking
Walking Grade: 1 & 2

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.

Holiday Highlights

  • 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

What’s included

  • 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

Trip Notes

Trip notes are detailed, downloadable PDF’s for each holiday, please click the button below to find the right trip notes for your departure date.

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. Some of our breaks have more than one itinerary. To check which itinerary is running on your holiday date please refer to the Dates, Prices & Trip Notes tab.

You're welcome to check in from 4pm onwards.

Enjoy a complimentary Afternoon Tea on arrival.


Option 1 - To Carisbrooke Castle

Distance: 5 miles (8km)

Ascent: 550ft (180m)

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

Highlight: There's lots of time to explore the castle. A real highlight is watching the donkeys turn the treadmill to raise water from the well.

Option 2 - Shorwell & Carisbrooke

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.

Option 3 - The Three Trails

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!


Option 1 - Coastal Path from Gore Down to Ventnor

Distance: 7 miles (11km)

Ascent: 750 feet (240m)

In Summary: This walk takes the coast path past St Catherine's Point, before passing through Niton Village, and then rejoining the coast path through the undercliff and into Ventnor.

Highlight: Discover the Undercliff; a natural sun trap, rich with verdant vegetation, created by a series of landslips over the centuries.

Option 2 - Chale Church to Ventnor

Distance: 8½ miles (13.5km)

Ascent: 1100 feet (320m)

In Summary: This walk starts along the coast path, before diverting inland to Whitwell, before rejoining the coast path at the undercliff and continuing to Ventnor

Highlight: Enjoy great coastal views of St Catherine's Point.

Option 3 - Chale Green to Ventnor

Distance: 10 miles (16km)

Ascent: 1400 feet (420m)

In Summary: This walks starts inland before reaching the coast path at St Catherine's point, then taking in Whitwell and the undercliff into Ventnor

Highlight: A great variety of inland and coastal walking, offering great views.


Discover more about Freshwater Bay House and the local area for ideas on how to fill your free day. 


Option 1 - Over Tennyson Down

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.

Option 2 - Headon Warren & The Needles

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.

Option 3 - West Wight Circuit

Distance: 12 miles (19km)

Total ascent: 1,550 feet (480m)

In Summary: A repeat from earlier in the week for 7 nIght guests. 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 - Wooded Trails & Grassy Downs

Distance: 6½ miles (10.5km)

Ascent: 750 feet (220m)

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.

Option 2 - Over the Downs

Distance: 8½ miles (13½km)

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.

Option 3 - Eight Downs Horseshoe

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.


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 atop 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.

 

Rooms

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 Classic, Premium and Superior 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 ‘Classic’ rooms are en-suite and furnished to a high standard. There are also several ‘Premium’ and ‘Superior’ Rooms that are either larger or have a desirable view, a more luxurious mattress and larger television – upgrade your stay for just an extra £15-25 per person per night. You can choose a specific room for an extra £30 per room, subject to availability. Upgrade supplements still apply.

Facilities

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 (open in summer season) – 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 Mermaid 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. Food at Freshwater Bay House is varied with a strong emphasis on the use of seasonal British produce. Our experienced chefs create each dish using only the freshest ingredients and, when in season, use home grown herbs and vegetables taken from our own gardens to give a true taste of the local area.

Accessibility

For accessibility and assistance information, please contact our expert team on 020 3974 8865 or view the accessibility information online for Freshwater Bay House

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Getting to Freshwater Bay House

Find out more about this location including travel details and room types.

More Information

Guest Reviews

Duration:
6 nights
Type:
Guided Walking
Walking Grade:
1

Fully Booked

020 3974 8865

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