Isle of Wight Guided Walking Tour 2021

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8 Days / 7 Nights
Availability : April to October
Start: Freshwater Bay House, Freshwater Bay, Isle of Wight, England
End: Freshwater Bay House, Freshwater Bay, Isle of Wight, England
Isle of Wight Guided Walking Tour: 7 nights based at Freshwater Bay House, Freshwater Bay, Isle of Wight

Contact DHTour at 1-888-597-3519 or 905-639-9954 or dhtour@dhtour.ca to book.

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.

Tour Details

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

Pick Up Location & TIme

Freshwater Bay House, Freshwater Bay, Isle of Wight PO40 9RB (Google Map)
4:00pm – You’re welcome to check into the country house hotel from 4pm onwards.

Drop off Location & Time

Enjoy a leisurely breakfast before making your way onward.

Price Includes

  • High quality en-suite upgraded accommodation at Freshwater Bay House
  • Excellent food in our country house, full board (B,L,D daily)
  • The services of our knowledgeable leader, ensuring you get the most from your holiday
  • 5 days guided walking + 1 free day
  • Choice of up to three guided walks each walking day
  • Transport to and from the walks
  • Use of our comprehensive Discovery Point

Meals

  • 7 breakfasts
  • 6 lunches
  • 7 dinners
  • 0 teas

Price Excludes

  • Airfare
  • Transfers
  • Pre / Post hotel nights
  • Travel to/from the Country Hotel (The nearest train station is Lymington Pier on the mainland. This is immediately adjacent to the ferry terminal)
  • Admissions (please allow approx. £10 per day for entrances)
  • Driver / Tour Leader gratuity is at your discretion
  • Travel Insurance
What to Expect
Isle of Wight Guided Walking Tour Walking Grade: 1 & 2.

Enjoy a full day’s walking with fellow guests and leave all the planning and navigation to us; it’s what we do best. Nobody knows the UK’s best places to walk like us. Our knowledgeable leaders make sure you’re never short of the inside story on local features, viewpoints and places of interest.

  • Unpack once
  • Accommodation at a country house hotel
  • Full Board Meals – from dinner on arrival day to breakfast on departure day
  • Knowledgeable leader
  • Choice of up to 3 walks per walking day with required transport

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. 

Walking Grades Explained:

  • Grades 1 & 2 – Leisurely walking grades
  • Grades 3 & 4 – Moderate walking grades
  • Grades 5 & 6 – Challenging walking grades
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.

Essentials

  • 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.

Recommended

  • 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
Version 1 Itinerary

Day 1Arrival Day

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

Accommodation: Freshwater Bay House (D)

Day 2Tennyson Down and Alum Bay

Option 1 – Over Tennyson Down
Distance: 7 miles (11km)
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: 8.5 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)
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.

Accommodation: Freshwater Bay House (B, L, D)

Day 3Walks around Eastern Wight

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: 8.5 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.

Accommodation: Freshwater Bay House (B, L, D)

Day 4Free day

A free day for you to explore the local area or to relax in the Country House. Our Discovery Points help you make the most out of your free day. There’s plenty of maps and a selection of the best local walking routes, as well as weather forecasts and public transport options – plus details about other places to visit. 

Accommodation: Freshwater Bay House (B, L, D)

Day 5Shorwell and Carisbrooke Castle

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: 12.5 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!

Accommodation: Freshwater Bay House (B, L, D)

Day 6Over the downs to Ventnor Botanic Garden

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: 5.5 miles (9km)
Ascent: 800 feet (250m)
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: 10.5 miles (16.5km)
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.

Accommodation: Freshwater Bay House (B, L, D)

Day 7Calbourne to Freshwater Bay

Option 1 – Calbourne to Freshwater
Distance: 6.5 miles (10.5km)
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. 

Option 2 – Mottistone Down
Distance: 8.5 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.

Accommodation: Freshwater Bay House (B, L, D)

Day 8Departure Day

Enjoy a leisurely breakfast before making your way home. (B)

Version 2 Itinerary

Day 1Arrival Day

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

Accommodation: Freshwater Bay House (D)

Day 2Tennyson Down and Alum Bay

Option 1 – Over Tennyson Down
Distance: 7 miles (11km)
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: 8.5 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)
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.

Accommodation: Freshwater Bay House (B, L, D)

Day 3Godshill and Appuldurcombe House

Option 1 – Godshill & Appuldurcombe
Distance: 5 miles (8km)
Ascent: 800 feet (240m)
In summary: A delightful circuit from the village of Godshill takes us to the Worsley Monument and the ruined shell of Appuldurcombe House.
Highlight: There’s plenty of time to explore Godshill and admire its quintessential thatched cottages and historic church.

Option 2 – Over the Downs
Distance: 8.5 miles (13.5km)
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: 10.5 miles (16.5km)
Ascent: 1,450 feet (440m)
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.

Accommodation: Freshwater Bay House (B, L, D)

Day 4Free day

A free day for you to explore the local area or to relax in the Country House. Our Discovery Points help you make the most out of your free day. There’s plenty of maps and a selection of the best local walking routes, as well as weather forecasts and public transport options – plus details about other places to visit. 

Accommodation: Freshwater Bay House (B, L, D)

Day 5Shorwell and Carisbrooke Castle

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: 12.5 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!

Accommodation: Freshwater Bay House (B, L, D)

Day 6Walks through the Undercliff

Option 1 – Ventnor to Shanklin
Distance: 5.5 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: 8.5 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 – Chale Green to Shanklin
Distance: 11.5 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.

Accommodation: Freshwater Bay House (B, L, D)

Day 7The Yar Valley or the Tennyson Trail

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: 8.5 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: 11.5 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.

Accommodation: Freshwater Bay House (B, L, D)

Day 8Departure Day

Enjoy a leisurely breakfast before making your way home. (B)

Dates and Prices
Version 1
Departure Dates
Per person (single or twin) Single in a double room
2021: May 1, 22 $2,170 $2,450
2021: June 5, 26 $2,170 $2,450
2021: July 10 $2,170 $2,450
2021: August 28 $2,170 $2,450
2021: September 4, 11 $2,170 $2,450
2021: September 25 $2,000 $2,280
2021: October 8 $2,000 $2,280
Version 2
Departure Dates
Per person (single or twin) Single in a double room
2021: April 9, 24 $2,000 $2,280
2021: May 15, 29 $2,170 $2,450
2021: June 19 $2,170 $2,450
2021: July 3, 17 $2,170 $2,450

Dates shown in green are guaranteed departures.

Pricing

Pricing is per person (pp) based on single/twin/double occupancy.

Supplement applied for single in a double room.

Rates are in $ CAD. Rates include room upgrade (better) and membership fees. 


Contact DHTour at 1-888-597-3519 or 905-639-9954 or dhtour@dhtour.ca to book.

Ask us for the best available pricing for your dates & choice of airline. We can assist in your travel to/from the Country House.

This tour is also available in 3 or 4 night duration. 

This holiday includes active sightseeing and you should expect to spend lots of time on your feet.

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. Sometimes things happen beyond our control – the weather, traffic jams or changes at the places we visit. If we need to adjust your holiday programme, for whatever reason, your leader will help smooth the way.

Travel Details:
Address is: Freshwater Bay House, Freshwater Bay, Isle of Wight PO40 9RB

By Rail:
The nearest train station is Lymington Pier on the mainland. This is immediately adjacent to the ferry terminal.

By Ferry:
The Wightlink Lymington to Yarmouth ferry is the most convenient for Freshwater Bay. Alternatively the Red Funnel Southampton to East Cowes ferry is often the cheapest option if you want to take your car to the Isle of Wight

By Taxi:
It is possible to get a taxi to Freshwater Bay House. The 5-mile journey from Yarmouth ferry port takes approximately 15 minutes. You can pre-book a taxi from our recommended taxi company, Alpha Cars. As a guide price, it cost £20 per 4-seat taxi in 2019. 8-seat taxis are also available at a higher rate. Please pre-book your taxi at least 7 days in advance by contacting:

Alpha Cars*
Tel: +44 (0) 1983 280280
Email: rogerc@alphaiow.co.uk
The return taxi journey can be arranged on your behalf by the Freshwater Bay House Manager.
*Alpha Cars is not owned or managed by us.

By Car:
From Yarmouth turn right out of the ferry terminal onto the A3054 and over the bridge across the River Yar. After 1 mile turn left down Pixley Hill, signposted to Freshwater Bay. Turn left at Freswater Garage and continue along Afton road. At the Lifeboat station turn right and follow the road round passing the Albion Hotel on the left. The entrance to Freshwater Bay House is the next driveway on your left.

From East Cowes: Follow signs for Newport following A3021 and then A3054. Continue through Newport and Carisbrooke. Turn left onto the B3401 through Calbourne. At the T junction with Afton Road (A3055) turn left and then right by the Lifeboat station and follow the road round passing the Albion Hotel on the left. The entrance to Freshwater Bay House is the next driveway on your left.

Alternatively leave your car on the mainland and travel to the Isle of Wight as a foot passenger. There is a pay and display car park at Lymington Pier – price approximately £8.50 per day.

Hotel Descriptions
4

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.

Address: Freshwater Bay House, Freshwater Bay, Isle of Wight PO40 9RB

Room Amenities: 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.

Hotel Amenities: 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.

Map

Photos