4-Night Isle of Wight Guided Walking Holiday

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Duration: 4 nights
Type: Guided Walking
Walking Grade: 1 & 2
from £435pp £218pp

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
  • 3 days guided walking
  • Use of our comprehensive Discovery Point

Trip Notes

Trip notes are detailed, downloadable PDFs for each holiday.

Download Trip Notes

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 - 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 - 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 - 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. 


 

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 - 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 - Ventnor to Shanklin

Distance: 5½ miles (9km)

Ascent: 950 feet (300m)

In Summary: Walk through the lush Undercliff. Our walk takes us from Ventnor's Botanic Gardens along the coastal path to Shanklin Old Village.

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

 

Option 2 - Niton to Shanklin

Distance: 8½ miles (13½km)

Ascent: 1,200 feet (360m)

In Summary: Soak up the sea air and views of the English Channel on a walk through the Undercliff from Niton to Shanklin Old Village.

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

 

Option 3 - Chale Green to Shanklin

Distance: 11½ miles (19km)

Ascent: 1,750 feet (540m)

In Summary: A journey along the length of Undercliff. We head over St Catherine's Down from Chale Green, with fantastic views down to the coast, where we join the coast path all the way to Shanklin.

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

 


Option 1 - Yar Valley

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.

 

Option 2 - The Longstone

 Distance: 8½ miles (13.5km)

Ascent: 1,050 feet (320m)

In Summary: Walk on top of the Downs from Shorwell to the ancient Longstone and along the Tennyson Trail back to Freshwater Bay.

Highlight: The Neolithic Longstone on Mottistone Down; according to legend this 13ft stone was thrown here by a giant!

 

Option 3 - Downland & Coast

Distance: 11½ miles (18.5km)

Ascent: 1,250 feet (380m)

In Summary: Walk over the Downs to the Neolithic Longstone, then descend to the coast and follow the coastal path back to Freshwater Bay .

Highlight: Enjoy the sweeping views along the island's south-west coast, as you walk over the chalk cliffs of Compton Down.

 


Enjoy a leisurely breakfast before making your way home. 


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 - Through the Undercliff

Distance: 6 miles (10km) 

Ascent: 600 feet (200m) 

In Summary:  Starting above St Catherines Point with fantastic views from the cliffs over St Catherines Lighthouse. You then head inland to the quaint village of Whitwell, before returning to the coast and the Undercliff from St Lawrence to Ventnor’s Botanic Gardens. 

Highlight: The vast collection of exotic and subtropical plant species at Ventnor Botanic Gardens.

 

Option 2 - Niton to Shanklin

Distance: 8½ miles (13.5km)

Ascent: 1,200 feet (360m)

In Summary: Soak up the sea air and views of the English Channel on a walk through the Undercliff from Niton to Shanklin Old Village.

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

Option 3 - Whale Chine to Shanklin

Distance: 11½ miles (18.5km) 

Ascent: 1,800 feet (540m)

In Summary: A journey along the length of Undercliff. Starting at Whale Chine we'll round St Catherine's Point before picking up the coastal path through Ventnor to Shanklin.

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

 


Option 1 - Brighstone and the Isle of Wight Pearl

Distance: 6 miles (10km)

Ascent: 660 feet (200m) 

In Summary: From Compton Farm we walk to Brighstone, passing the Longstone (a neolithic long barrow and ancient meeting point) and on to the coast and the Isle of Wight Pearl.     

Highlight: Excellent views to the South coast of the Island and the Isle of Wight Pearl - claimed to be the largest collection of pearls under one roof. 

 

Option 2 - Carisbrooke & Shorwell

Distance: 9 miles (14km)

Ascent: 1,050 feet (320m)

In Summary: Walk from Carisbrooke Castle over the downs via the pretty villages of Shorwell and Brighstone to the coast and the Isle of Wight Pearl.

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

 

Option 3 - Tennyson Trail

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 - Yar Valley

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.

 

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. We 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 the pretty village of Brighstone, then follow the coast path along the island’s beautiful southwest coast past the Isle of Wight Pearl and Hanover Point back to Freshwater Bay.

Highlight: Tides permitting, look out for the fossilised forest at Hanover Point.

 


Enjoy a leisurely breakfast before making your way home. 


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 - St Helens to Sandown

Distance: 7 miles (11km)

Ascent: 550 feet (160m)

In Summary: Cross the causeway at Bembridge Harbour then walk on top of the chalk cliffs of Culver Down, near the eastern tip of the island, and follow the coastal path to Sandown.

Highlight: The working windmill at Bembridge; one of the National Trust's smallest, but most fascinating, properties.

 

Option 2 - Ryde to Sandown

Distance: 8½ miles (14km)

Ascent: 750 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.

 

Option 3 - Havenstreet to Sandown

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.

 


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!

 


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.

 

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 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.

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 – 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.

Accessibility

For accessibility and assistance information, please contact our expert team on 020 3974 8865

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Getting to Freshwater Bay House

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

More Information

What to Bring

Essential Equipment

To enjoy walking/hiking comfortably and safely, footwear, clothing and equipment needs to be suitable for the conditions. Safety is our priority and Britain is famous for its changeable weather, so our advice is to come prepared for all eventualities.

  • Footwear with a good grip on the sole (e.g.Vibram sole) is the key to avoiding accidents
  • Walking/hiking boots providing ankle support and good grip are recommended (ideally worn in), and specialist walking socks to avoid blisters
  • Several layers of clothing, which can be added or removed, are better than a single layer (include spares)
  • Fabrics (lightweight and fast drying) designed for the outdoors are recommended
  • Waterproof jacket and waterproof over trousers
  • Warm hat and gloves. Gaiters are an optional but useful extra
  • Denim jeans and capes are not suitable on any walks
  • Rucksack with a waterproof liner
  • Thermos flask for hot drink
  • Water bottle (at least 1 litre)
  • Spare high-energy food such as a chocolate bar
  • Small torch
  • First aid kit – your leader’s first aid kit doesn’t contain any medication or blister kits (such as Compeed)

Optional Equipment

  • Walking poles are useful, particularly for descents
  • Insect repellent
  • Sun hat
  • Sunglasses
  • Sun cream
  • Camera

Guest Reviews

All holidays are subject to availability and prices are subject to change.
Non-member associate fee: £10 per person.

Holiday Prices

Date (Start - End) Version Price Status Trip Notes Book
2019
30 Sep - 04 Oct Version 1 (runs 2019/20) £495 £435 Unavailable
14 Oct - 18 Oct Version 1 (runs 2019/20) £495 £435 Save £60 Per Person Book Now
21 Oct - 25 Oct Version 2 (runs 2019/20) £495 £435 Save £60 Per Person Book Now
28 Oct - 01 Nov Version 1 (runs 2019/20) £435 £375 Save £60 Per Person Book Now
04 Nov - 08 Nov Version 3 (runs 2019/20) £435 £375 Save £60 Per Person Book Now
11 Nov - 15 Nov Version 3 (runs 2019/20) £435 £218 Save 50% Per Person Book Now
2020
16 Mar - 20 Mar Version 3 (runs 2019/20) £449 £364 Save £85 Per Person Book Now
30 Mar - 03 Apr Version 1 (runs 2019/20) £515 £430 Save £85 Per Person Book Now
06 Apr - 10 Apr Version 2 (runs 2019/20) £515 £430 Save £85 Per Person Book Now
10 Apr - 14 Apr Version 4 (runs 2020) £515 £430 Save £85 Per Person Book Now
05 May - 09 May Version 1 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
12 May - 16 May Version 2 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
02 Jun - 06 Jun Version 1 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
16 Jun - 20 Jun Version 1 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
23 Jun - 27 Jun Version 2 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
28 Jul - 01 Aug Version 1 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
25 Aug - 29 Aug Version 2 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
01 Sep - 05 Sep Version 1 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
08 Sep - 12 Sep Version 2 (runs 2019/20) £559 £489 Save £70 Per Person Book Now
28 Sep - 02 Oct Version 2 (runs 2019/20) £515 £445 Save £70 Per Person Book Now
19 Oct - 23 Oct Version 2 (runs 2019/20) £515 £430 Save £85 Per Person Book Now
26 Oct - 30 Oct Version 1 (runs 2019/20) £515 £430 Save £85 Per Person Book Now
02 Nov - 06 Nov Version 3 (runs 2019/20) £449 £364 Save £85 Per Person Book Now
09 Nov - 13 Nov Version 3 (runs 2019/20) £449 £364 Save £85 Per Person Book Now
Duration:
4 nights
Type:
Guided Walking
Walking Grade:
1

4 nights from £435pp £218pp

...or call 020 3974 8865

For group bookings of 10+ people click here

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