7-Night Isle of Wight Outdoor Escapes Holiday

Freshwater Bay at Sundown
Duration: 6 nights
Type: Outdoor Escapes
Walking Grade: 1 & 2
from £829pp £704pp

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 Experience the very best of the Island. Each day we'll offer three options, ranging from relaxing shorter strolls, to more challenging longer walks. Our flexible programme allows you to choose the option that suits your mood.

Holiday Highlights

  • By the range of guided walks, from spectacular strolls across Tennyson Down to Alum Bay in search of coloured sands, to routes through the Undercliff and spectacular longer stretches of the windswept southwest coast path.
  • By how much you can do in a short break when your guides know their stuff, from discovering a once secret rocket testing range and the area’s role in the space race, to trying the vintages produced at a vineyard and exploring the romantic setting of Carisbrooke Castle.
  • By the camaraderie and craic that comes from making discoveries and having adventures in a small group of like-minded people.

Moment of the weekend

When you realise what walked the shores of Compton Bay before you. We’ll introduce you to a local dinosaur expert and fossil hunter who will stroll the sands at low tide with you in search of evidence of life from the Cretaceous period. Look out for large three-toed iguanodon and theropod foot casts as you soak up dino-tidbits from the expert. Perhaps you’ll find fossilised bones, dinosaur teeth, or other artefacts that yesterday’s tide uncovered for the first time in 100 million years.

What’s included

  • High quality en-suite accommodation in our country house
  • Full board from dinner upon arrival to breakfast on departure day
  • 5 days guided walking; 1 free day
  • Use of our comprehensive Discovery Point
  • Choice of up to three guided walks each walking day
  • The services of HF Holidays Walking Leaders

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.

Join us at our Freshwater Bay Country House for an action-packed short break. If the weather is fine we can take a short pre-dinner stroll down to the beach to help get your bearings. After a delicious 3-course evening meal, there's time to relax with the rest of the group and look forward to the adventures to come. 

Choose from a choice of 3 guided walks. Soak up the breathtaking coastal scenery on walks to the Needles and the chalk cliffs of Tennyson Down. 

Option 1 - The Needles

Distance: 4 miles (6.5km) 

Ascent: 850 feet (260m) 

In Summary: A fabulous walk from Alum Bay to the Needles and over the chalk cliffs of Tennyson Down back to Freshwater; one of England's finest coastal walks. 

Highlight: Discovering the once secret rocket testing range, and the area's role in the space race. 


Option 2 - Along the chalk cliffs

Distance: 8½ miles (13.5km) 

Ascent: 1,250 feet (380m) 

In Summary: Head to the coast at Totland Bay then soak up glorious sea views as you round the Needles headland and return over Tennyson Down. 

Highlight: The heather-clad headland of Headon Warren is beautiful, and offers the best views of the Needles. 


Option 3 - West Wight Circuit

Distance: 13 or 16 miles (20.5km or 26km)

Ascent: 1,800 feet (540m) 

In Summary:  A true leg stretcher covering the western tip of the island and taking in magnificent sections of the Isle of Wight Coast Path, all the way back to Freshwater Bay. 

Highlight: A fantastic final leg, following the chalk cliffs of Tennyson Down. 


Discover the island's wild south-west coast, stopping to discover the remarkable dinosaur footprints with a local expert. 

Option 1 - Brighstone to Freshwater Bay

Distance: 6½ miles (10.5km)

Ascent: 550 feet (160m)

In Summary: Walk from Brighstone to the coast and the Isle of Wight Coast Path, and along to Freshwater Bay. 

Highlight: searching for evidence of Iguanodon or Theropod foot casts with our dinosaur experts.   


Option 2 - Calbourne to Freshwater Bay

Distance: 8½ miles (14km)

Ascent: 1,250 feet (380m) 

In Summary: Walk from Calbourne over the Downs to the coast for some fossil hunting before walking on to Freshwater Bay. 

Highlight: The chance to spot dinosaur footcasts with the help of our experts. 


Option 3 - Along the South West Coast

Distance: 11 miles (17.5km) 

Ascent: 1,250 feet (380m)

In Summary: Follow the coast path along the island’s windswept southwest coast from Blackgang to Freshwater Bay. 

Highlight: Stopping to spend time with the fossil experts, searching for evidence of dinosaurs.  


Choose from a choice of 3 guided walks that explore the east of the island. Take it easy with a stroll from Ventnor Botanic Gardens to Shanklin, or stride out on our long walks along the coast. 

Option 1 - The Undercliff

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: The unrivalled subtropical and exotic plant selection at Ventnor's Botanic Gardens are a must see. 

Option 2 - Niton to Shanklin

Distance:  8 miles (13km) 

Ascent: 1,150 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: an ice cream in Ventnor - Crave ice cream parlour was voted the UK's number 1 in 2018! 


Option 3 - Chale Green to Shanklin

Distance: 11½ miles (19km) 

Ascent: 1,750 feet (540m)

In Summary: 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: a quick visit to the 'pepperpot' - the oldest surviving medieval lighthouse in the UK. 


Enjoy walks to the enchanting Carisbrooke Castle, or stride out over the downs, following the Tennyson Trail. 

Option 1 - Carisbrooke Castle

Distance: 4 miles (6.5km)

Ascent: 450 feet (140m)

In Summary: A relaxing stroll over the Downs to the romantic setting of Carisbrooke Castle. We've left plenty of time for you to explore. 

Highlight: Meeting the donkeys that power the water wheel at the castle. 


Option 2 - Shorwell to 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: Snapping shots of 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: Walk along the spine of the island from Carisbrooke to Freshwater Bay. We’ll cross hills to Shorwell then pick up the Tennyson Trail along the Downs. 

Highlight: One of our most popular walks. Your celebratory pint at the end of the walk will be well deserved! 


Our field advisors are busy working on the final detail of our walks today. The walks will centre around beautiful Brading Down with highlights including the opportunity to sample the award winning local tipple at the Adgestone Vineyard, and a trip back to a bygone era on the Isle of Wight Steam Railway.  

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.



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 £15-25 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

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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

“There’s no such thing as bad weather, just the wrong type of clothing!” goes the adage. Come prepared for all eventualities and you’ll walk in comfort as well as safety. Britain’s famous for its changeable weather, so here’s our advice on what to wear and bring.


  • Waterproof walking boots providing ankle support and good grip.
  • A waterproof jacket and over-trousers
  • Gloves and a warm hat (it can be chilly at any time of the year)
  • Rucksack
  • Water bottle (at least 1 litre capacity)
  • A small torch (everywhere in winter, year round in mountains)
  • Sun hat and sunscreen
    Denim jeans and waterproof capes are not suitable on any walks.


  • Several layers of clothing, which can be added or removed
  • Specialist walking socks to avoid blisters.
  • A first aid kit inc plasters– your leader’s first aid kit doesn’t contain any medication
  • Sit mat (insulated pad to sit on when you stop for a break)

You might also want

  • Walking poles, particularly useful for descents.
  • Insect repellent
  • Flask for hot drinks
  • Rigid lunch box
  • Gaiters
  • Blister kit (eg Compeed) just in case
  • Waterproof rucksack liner

Guest Reviews

All holidays are subject to availability. Prices are subject to change.
Prices based on two people sharing. Supplements may apply.
Non-member fee: £10 per person.

Holiday Prices

Date (Start - End) Nights Itinerary Price Status Trip Notes Book
02 Oct - 09 Oct
6 Outdoor Escape £829 £704 Save £125 Per Person Trip Notes Book Now
6 nights
Outdoor Escapes
Walking Grade:

6 nights from £829pp £704pp

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