7 Night Isle of Wight Gentle Guided Walking Holiday
For golden sand beaches, rolling green hills, dramatic white cliffs, ancient woodland, and bags of Victorian charm, the Isle of Wight is the perfect island escape. Ideal for those wanting to discover its charms at a more relaxed pace, this gentle guided walking holiday rewards with breathtaking trails, big-name historic attractions, comfortable accommodation, and more. You’ll also enjoy a choice of up to three different-grade daily walks, including a gentle walk of three to four miles.
What you’ll love
- Discovering the stunning landscape of the Isle of Wight on foot
- Soaking up panoramic views of the dramatic coastline
- Visiting golden sand beaches and picturesque villages
- Spending time with like-minded people in the great outdoors
- Finding new routes and places to explore with your HF Holidays Leader
- Staying at Freshwater Bay House, just a skip from Tennyson Down
What’s included
- Comfortable en-suite accommodation in our country house
- Cream tea on arrival day
- Cooked or continental breakfast every morning
- Daily packed lunches
- Three-course evening meals, plus tea & coffee
- Guided walking with experienced HF Holidays Leaders
- Choice of up to three guided walks (on walking days)
- All transport to and from walks where necessary
- Easy-to-follow routes, maps, and information in our Discovery Point if you want to explore independently
Trip Notes
Easy to download as a PDF, our trip notes provide detailed information for every holiday. Please click below to find the trip notes for your departure date.
All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take alternative routes or adapt the running order for weather and/or operational reasons.
Enjoy a complimentary cream tea on arrival, served from 4.30pm.
Option 1 - Alum Bay and the Downs
Distance: 4 miles (6.5km)
Ascent: 800 feet (260m)
In summary: Explore 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
Highlights: Alum 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: 1,200 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.
Highlights: 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 3 - Tennyson Down and the Needles
Distance: 8 miles (13km)
Total ascent: 1,500 feet (460m)
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 1 - The Long Stone & Brighstone
Distance: 3½ miles (5km)
Ascent: 300 feet (100m)
In summary: Walk to the Long Stone, a neolithic long barrow and ancient meeting point, then on over the hills to Brighstone village.
Highlights: Legend 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 - Wooded Trails & Grassy Downs
Distance: 6½ miles (10.5km)
Ascent: 750 feet (240m)
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 3 - Mottistone Down via Downton
Distance: 8 miles (13km)
Ascent: 900 feet (280m)
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.
Highlights: The final section over Compton Down enjoys splendid views over Freshwater Bay, and back along the island's southwest coast.
Discover more about Freshwater Bay House and the local area for ideas on how to make the most of your free day.
Option 1 - Around Carisbrooke
Distance: 3 miles (4.5km)
Ascent: 350 feet (100m)
In summary: Follow the Shepherd's Trail through the fields and along an ancient trackway to Carisbrooke Castle.
Highlights: Take time to explore this well-preserved castle. Don't forget to walk around the walls and see the donkey powered well.
Option 2 - Shorwell to Carisbrooke
Distance: 5 miles (8km)
Ascent: 550 feet (160m)
In summary: Starting in the village of Shorwell the walk heads over the downs to Carisbrooke Castle and the town of Carisbrooke.
Highlight: Snapping shots of picturesque Shorwell with its thatched cottages and historic church.
Option 3 - Brighstone to Carisbrooke
Distance: 7½ miles (11.5km)
Ascent: 1100 feet (340m)
In summary: Starting from Brighstone we pass through Shorwell before crossing open countryside until we arrive at Carisbrooke Castle.
Highlight: Enjoy views of the coast, and the south of the Isle of Wight before exploring the historic roots of the Carisbrooke Castle.
Option 1 - Bonchurch To The Botanic Gardens
Distance: 3 miles (4.5km)
Ascent: 300 feet (80m)
In summary: Our walk starts by visiting the village of Bonchurch. We then walk the promenade before reaching the classic Victorian seaside resort of Ventnor. We then take the coastal path past Steephill Cove on our way
to complete our walk at the botanic gardens at Ventnor.
Highlights: Bonchurch is a very old village, known to be inhabited in prehistoric times. Many well-known literary figures have lived in Bonchurch, including Tennyson, Macauley, Dickens, Thackeray and Elizabeth Sewell.
Option 2 - Through the Undercliff
Distance: 6 miles (10km)
Ascent: 600 feet (180m)
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 3 - Chale Church to Ventnor Coast
Distance: 7½ miles (11.5km)
Ascent: 1000 feet (300m)
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 1 - Yarmouth
Distance: 3½ miles (5.5km)
Ascent: 150 feet (60m)
In summary: Walk beside the tidal River Yar to the historic town of Yarmouth. Take time to explore the cobbled streets and quaint shops and cafes, before catching the Breezer bus back to Freshwater Bay.
Highlights: Opened in 1876, Yarmouth Pier is the UK's longest wooden pier and stretches 186 metres into the Solent.
Option 2 - 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.
Highlights: The salt marsh, reedbeds and mud flats of the Yar Estuary are a great place to see wildfowl and waders.
Option 3 - Yar Valley and The Three Forts
Distance: 8 miles (13km)
Ascent: 550 feet (180m)
In summary: Walk through Golden Hill Country Park to the coast at Fort Victoria with uninterrupted views across the Solent to Hurst Castle on the mainland. Continue on the Coastal Path into the old port of Yarmouth and return to Freshwater beside the River Yar.
Highlight: A walk full of history from the Victorian forts at Golden Hill & Fort Victoria to the remains of Henry Vlll’s castle at Yarmouth.
Enjoy a leisurely breakfast before making your way home.
Freshwater Bay House
Chalky white cliffs and eyebrow-arching sea views set the tone for the delights that follow at this county house on the Isle of Wight - Queen Victoria's favourite island that’s just a ferry hop from the South Coast. The location is as gorgeous as it gets; to the south of the village of Freshwater, within pebble-throwing distance of its namesake bay, and just a skip from Tennyson Down. You’ll also be within easy reach of the area’s showstoppers, including the imposing Stag and Mermaid rocks, the multi-coloured sands of Alum Bay, the remarkable Ventnor Botanic Gardens, and the 125-million-year-old dinosaur footprints at Compton Bay. And then, of course, there’s the Needles Old Battery for the ubiquitous photo opportunity and the best views of The Needles.
Rooms
Designed with your comfort in mind, Freshwater Bay House has 43 well-appointed guest rooms available in three categories: Classic, Premium, and Superior.
Classic Rooms are comfortable en-suite guest rooms, ideal for a peaceful night's sleep. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, and shower gel), and a TV.
Premium Rooms are more spacious en-suite guest rooms*. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, body lotion, shower gel), and a 32-inch TV. Extras include bathrobes, slippers, and comfortable mattresses.
Superior Rooms are even more spacious en-suite guest rooms offering upgraded views of the surroundings*. Amenities include free Wi-Fi, tea and coffee-making facilities, toiletries (hand wash, shampoo, body lotion, shower gel), and a 32-inch TV. Extras include bathrobes, slippers, and comfortable mattresses.
We love: Rooms 19 and 20 on the first floor for their lovely sea views. Rooms 18 and 22 are both corner rooms overlooking the bay and Tennyson Downs. The more spacious Room 24 has five large windows overlooking the gardens and bay as well as a private sitting room. Room 39 on the second floor is a corner room with a bathtub.
The Choose Your Room service is available at our UK country houses, allowing you the option of choosing and confirming a specific room for an extra charge of £30 per room. This is subject to availability. Upgrade supplements apply.
Check in & check out
You are welcome to check in from 4:00pm at the earliest. On arrival, you’ll enjoy a complimentary cream tea and get to meet your fellow guests, our HF Holidays Leaders, and the rest of the friendly team.
On the day of departure, we kindly ask all guests to check out by 10:00am. You’ll be asked to settle your bill prior to leaving. You may, of course, make a charitable donation to our HF Holidays Pathways Fund if you wish. Please note that we only accept card payments.
Room supplements
| Superior | Premium single | Premium double/twin | Choose your room |
| £25 pppn | £20 pppn | £20 pppn | £30 per room |
*Views and layout reflect each properties unique character and location
About your stay
A warm welcome
We want you to feel comfortable from the moment you arrive. You’ll find a welcome pack in your room with guest registration forms, menus, order forms for dinners and picnic lunches, the Wi-Fi password, and the front door code. Our houses are locked at night, so we recommend noting the Duty Manager’s number on arrival in case of an emergency (or getting locked out).
Evening entertainment
While evening entertainment varies from house to house, the HF Holidays Big Pub Quiz held after dinner on Wednesdays is a weekly staple. Your HF Holidays Leader may be around for tips on guided and self-guided walking routes as well as visit-worthy local attractions.
Walks talks
Our HF Holidays Leaders host guided walking information briefings before dinner on arrival days. This is followed by a group Walks Talk for information on the following day’s walking delights (held before dinner every evening). Self-guided walking guests are, of course, welcome.
The walking day
Prior to setting off on walks, your HF Holidays Leader will run you through a short safety briefing. There’s also an up-to-date weather forecast on display at the house to ensure you have appropriate clothing and footwear. If you choose to do your own walks or are on a self-guided walking holiday, we ask that you please complete an Independent Walker Card each day. These can be found near the Discovery Point in the house.
Food & drink
Led by experienced chefs, we serve a wide range of dishes made with fresh and seasonal ingredients. We always aim to source the best produce available and use home-grown herbs and vegetables from our own gardens whenever possible. Additionally, we have a licensed bar with beers, soft drinks, and a superb selection of spirits. Full-board comes as standard and includes a cream tea on arrival and a hearty breakfast on departure day.
HF Holidays understands the importance of managing allergens effectively to ensure food is safe for guests with food allergies. Whilst we are always able to confidently inform guests which allergens are present in our ingredients and dishes, we are unable to guarantee absolute freedom from the 14 main allergens in our kitchens. Vegetarian and vegan menu choices are available. If you have allergies, food intolerances, or any special dietary requirements, please inform our reservation team at the time of booking.
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
Getting to Freshwater Bay House
Find out more about this location including travel details and room types.
More InformationAddress
Freshwater Bay House
Freshwater Bay
Isle of Wight PO40 9RB
Tel: +44 (0)1983 753854
By taxi
From Yarmouth ferry port it’s a five-mile taxi journey that takes approximately 15 minutes. We recommend booking your taxi at least seven days in advance as availability may be limited.
For pricing, please contact the taxi company directly.
Taxi companies in the area include:
CRAZY CABS
Tel: +44 (0)7475 662350
Rayner’s Taxis
Tel: +44 (0)1983 752784
I Cabs
Tel: +44 (0)7553 567567
A return journey can be arranged on your behalf by the HF Holidays House Manager at Freshwater Bay.
*HF Holidays does not own or manage any of the above taxi companies.
By train
The nearest station is Lymington Pier on the mainland which is adjacent to the ferry terminal.
Check National Rail for train times and routes.
By ferry
You have two ferry options. 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.
HF Holidays member discount
If you’re a member, you can get 15% off car travel and 20% off foot travel with Wightlink Ferry. For full details visit www.wightlink.co.uk/HFHolidays.
By car
From Yarmouth
Turn right out of the ferry terminal onto the A3054 and cross the bridge. After one mile, turn left down Pixley Hill, signposted Freshwater Bay. Turn left at Freshwater Garage and continue along Afton Road. At the lifeboat station turn right and follow the road round. Freshwater Bay House is on your left.
From East Cowes
Follow signs for Newport, taking the A3021 and then A3054. Continue through Newport and Carisbrooke. Turn left onto the B3401 through Calbourne. At the junction with Afton Road (A3055), turn left and then right by the lifeboat station, and follow the road round to Freshwater Bay House.
Or you can leave your car on the mainland (there’s a pay and display car park at Lymington Pier) and travel on the ferry as a foot passenger.
By air
The nearest airport is Southampton Airport.
From Southampton Airport Parkway station (adjacent to the airport terminal) there are regular trains to Lymington Pier, taking about 40 minutes. From here, you’ll need to catch the ferry over to the Isle of Wight.
Otherwise, the best options are London Heathrow or London Gatwick airports for connecting trains to Lymington Pier.
Check National Rail for the best routes and train times.
The UK has a famously unpredictable climate so it's best to be prepared for weather that’s sunny one minute and raining the next. To make it easier, here’s a list of items you should consider packing.
Essentials
- Suitable footwear such as waterproof walking boots that provide ankle support and good grip
- Waterproof and windproof jacket
- Comfortable clothing (jeans & waterproof capes are not suitable)
- Mid-layer(s) to keep you warm. Fleeces make a good choice
- Waterproof overtrousers
- Gloves and a warm hat
- Rucksack with waterproof liner
- Flask for hot drinks
- Water bottle (at least 1 litre capacity)
- Sunscreen
- UV sunglasses
Recommended
- Several base layers (long-sleeve or short-sleeve)
- Cushioned walking socks to avoid blisters
- First aid kit, including plasters and insect repellent
- Sit mat
- Waterproof pouch for valuables
- Rubbish bag (remember to always leave no trace)
- Wallet/purse
- Camera
- First-aid kit
Freshwater Bay House Calendar
- Guided Walking
- Self-Guided Walking
- Special Interests
- Unavailable to Book
Guest reviews
All holidays are subject to availability. Supplements may apply.
Non-member fee: £30 per person.
All our carefully-curated itineraries are designed by our experts. While we make every effort to adhere to the described itinerary, we may take an alternative route, or vary the running order for weather and/or operational reasons.
Holiday prices
| Date (Start - End) | Itinerary | Double / Twin Room | Single Room | Notes / Offers | Trip Notes | Book | ||
|---|---|---|---|---|---|---|---|---|
| 2025 | ||||||||
|
05 Apr - 12 Apr 2025 7 nights |
Gentle Walks Single from £1,089 Double from £1,089 pp |
from £1,089 pp |
from £1,089 |
Trip Notes
|
Book Now | |||
|
20 Sep - 27 Sep 2025 7 nights |
Gentle Walks
Single Call to Enquire
Double from £1,239 pp |
from £1,239 pp |
Call to Enquire |
Trip Notes
|
Book Now | |||
159Kg of CO₂e
Average carbon footprint per person Learn More
