4-Night Isle of Wight Gentle Guided Walking Holiday

Sunset on Limerstone Down, Isle of Wight
Duration: 4 nights
Type: Gentle Walks
Walking Grade: 1 & 2
from £515pp

The Isle of Wight is a world away from the bustle of the mainland. On this Gentle Guided Walking holiday you'll discover 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 to discover the varied beauty of the Isle of Wight on foot
  • Experience this magnificent island at a gentle pace with plenty of time to admire your surroundings
  • Let our experienced leader bring classic routes and offbeat areas to life
  • Admire panoramic views from coastal paths
  • 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

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

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 - Around Carisbrooke

Distance: 3 miles (4.5km) 

Ascent: 350 feet (100m) 

In SummaryFollow the Shepherd's Trail through the fields and along an ancient trackway to Carisbrooke Castle. 

HighlightsTake time to explore this well-preserved castle. Don't forget to walk around the walls and see the donkey powered well. 

 

Option 2 - To Carisbrooke Castle

Distance: 6 miles (10km) 

Ascent: 700 feet (210m) 

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

HighlightsTake 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 3 - Shorwell and Carisbrooke

Distance: 9 miles (14km) 

Ascent: 1,150 feet (360m) 

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

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

 

 


Option 1 - Alum Bay and the Downs

Distance: 4½ miles (7km) 

Ascent: 350 feet (100m) 

In SummaryExplore Alum Bay and the Needles Old Battery and New Battery before a glorious walk atop the chalk cliffs of Tennyson Down, offering magnificent views over the western half of the island 

HighlightsAlum Bay with it's coloured sands. The sand was once used for sand painting pictures, a popular craft in Victorian times. 

 

Option 2 - Over Tennyson Down

Distance: 7 miles (11km) 

Ascent: 1,250 feet (380m) 

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

HighlightsThe 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 3 - Headon Warren & Needles

Distance: 8½ miles (13.5km) 

Ascent: 1,250 feet (380m) 

In SummaryHead to the coast at Totland Bay then soak up glorious sea view as you round the Needles headland and return over Tennyson Down. 

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

 


Option 1 - The Long Stone & Brighstone

Distance: 4½ miles (7km) 

Ascent: 350 feet (100m) 

In SummaryWalk to the Long Stone, a neolithic long barrow and ancient meeting point, then on over the hills to Brighstone village. 

HighlightsLegend has it that St Catherine and the Devil had a contest to see who should control the Isle of Wight. The Long Stone’s tall iron sandstone pillar was supposedly thrown by St Catherine. 

 

Option 2 - Calbourne to Freshwater

Distance: 6½ miles (10.5km) 

Total ascent: 800 feet (240m)

In Summary: Walk from Calbourne to Freshwater Bay via the Downs. 

HighlightsThe 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 3 - Mottistone Down

Distance: 8½ miles (14km) 

Ascent: 1,100 feet (340m) 

In SummaryFrom Winkle Street ascend over the Downs, descending Mottistone Down to the south coast. We then follow the coastal path back to Freshwater Bay.  

HighlightsThe final section over Compton Down enjoys splendid views over Freshwater Bay, and back along the island's southwest coast. 

 


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

  • 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
2020
20 Apr - 24 Apr 2019 Itinerary £515 Available Book Now
Duration:
4 nights
Type:
Gentle Walks
Walking Grade:
1

4 nights from £515pp

...or call 020 3974 8865

For group bookings of 10+ people click here

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