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  • The Isle of Wight Coast Path Guided Trail Holiday
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The Isle of Wight Coast Path Guided Trail Holiday

Guided trails in Isle of Wight

7 nights

May, Jun - Oct

Grades 3

168kg CO2

7 nights from

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Members

From

£1,099

 

Non-members

From

£1,129

 

Groups of 10+

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020 3974 8865

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With miles of coastline to explore and more than half the island bestowed National Landscape status, the Isle of Wight has plenty of walks worth shouting about. But by far the most standout of them all is the Isle of Wight Coastal Footpath – a 71-mile route around the entire island that raises the bar for history, nature, and big-name sights. This guided trail holiday ticks off all the highlights including the chalk headlands of the Needles and Culver Cliff, the Victorian seaside resort of Ventnor, and Osborne House – Queen Victoria’s favourite summer residence.

What You’ll Love

  • Walking the full circuit of the Isle of Wight coast
  • Having all planning and navigation taken care of
  • The chance to spot rare flora and fauna
  • The dramatic chalk headlands of the Needles and Culver Cliff
  • Soaking up excellent coastal views
  • Staying in the comfort of Freshwater Bay House

What's Included

  • Comfortable en-suite rooms 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 walks with an experienced HF Holidays Leader
  • All transport to and from walks where necessary
  • Get 15% off car travel and 20% off foot travel via www.wightlink.co.uk/HFHolidays

Trip Suitability

This Guided Walking/Hiking Trail is graded 3 which involves walks/hikes on generally good paths, but with some long walking days. There may be some sections over rough or steep terrain and will require a good level of fitness as you will be walking every day. It is your responsibility to ensure you have the relevant fitness required to join this holiday.

Your fitness

We want you to be confident that you can meet the demands of each walking day and get the most out of your holiday. Please be sure you can manage the mileage and ascent detailed in the daily itineraries. It is important for your own enjoyment, and that of your fellow guests that you can maintain the pace.

It makes a lot of sense to spend time getting some additional exercise before your holiday. We suggest that you try to fit in a number of longer walks, including some on hilly terrain. Other exercises such as cycling, jogging and swimming are also excellent for developing increased stamina.

Itinerary

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.

Close all Expand all

Check-in at the hotel is available from 16:00. If you are a member you can arrive at the house from 14:00. Enjoy a complimentary cream tea at 16:30 and meet other guests.

From Freshwater Bay we face an ascent over the chalk cliffs of Compton Down, passing Hanover Point with its fossil forest. Along these cliffs you will see evidence of the battle against the sea. We reach the Blackgang Chine theme park where we ascend to the Gore Down viewpoint for a spectacular view back along the coast.

13 miles (21km) with 1,650 feet (500m) of ascent.

This section of coast has been prone to erosion and for much of the day we'll walk through the 'Undercliff' or on the escarpment cliffs above. Blackgang is on one of the most dramatic sections of this inland cliff and we pass St Catherine’s Point, the southern-most tip of the island. We continue to the village of St Lawrence before descending to the coast, passing the Botanic Gardens into the Victorian seaside town of Ventnor. We follow the promenade to Bonchurch with its ancient church, then through the richly vegetated Landslip (so named as it suffered in the great landslip of 1810), to Shanklin with its Victorian elegance. We follow the promenade to the resort of Sandown.

12 miles (19.5km) with 1,350 feet (410m) of ascent.

Please note, there has been a landslip on the coast path between Ventnor and Shanklin. For the time being, we will be using the public service bus to bypass this section. The resulting walks statistics are: 10.6 miles (16.9 km).

From Sandown we ascend the chalk clifftops of Culver Down, before passing the cliffs of Whitecliff Bay as we walk to Bembridge at the eastern tip of the island. Around the harbour we pass the tidemill and cross a causeway to the beach at St Helens Duver. As we follow the coast to Ryde, you'll see the Solent Forts, built in the early 19th-century to guard the approaches to Portsmouth against French invasions.

11 miles (17.5km) with 800 feet (250m) of ascent.

Around the northern tip of the island from Ryde we head west past the ruins of Quarr Abbey, a once-flourishing Cistercian Monastery, and on past Fishbourne with its ferry boats to Portsmouth and to Wootton Bridge. The path heads inland around Queen Victoria’s Osborne House estate. To avoid road walking, we take a bus to East Cowes and cross the chain-ferry to Cowes. We pass the Royal Yacht Squadron Club House, with its 22 bronze cannons, to Egypt Point and Gurnard Bay.

9½ miles (15.5km) with 900 feet (270m) of ascent.

We ascend the cliffs above Gurnard Bay, with magnificent views across the Solent and Southampton Water. After Thorness Bay the coastal path heads inland around the tidal creeks of the Newtown River. We pass the villages of Porchfield and Newtown. Newtown was the Island’s capital in the Middle Ages and once a thriving port and commercial centre. Continuing over the causeway to Shalfleet we head back to the coast at Hamstead Point and on to Cranmore.

11½ miles (18.5km) with 800 feet (240m) of ascent.

We pass Yarmouth with its historic castle and busy harbour and continue along the coast past Fort Victoria with views over the Solent to Hurst Castle. After Totland Bay, we ascend onto Headen Warren with its Bronze Age camp; a delightfully peaceful spot before the bright lights and music of the Alum Bay theme park. The most dramatic section of the coast path is the Needles; the chalk stacks that mark the western tip of the island before the outstanding final section along the chalk cliffs of Tennyson Down back to Freshwater Bay.

12 miles (19km) with 1,350 feet (410m) of ascent.

Enjoy a leisurely breakfast before making your way home.

Download trip notes

Daily Walk Options

Grade 3

Medium Walks

Walks follow well-defined paths, though often in hilly or upland areas, or along rugged coastal footpaths. These may be rough or steep in sections and will require reasonable fitness.

Accommodation

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.

 

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, HF Holidays Inter-House Quiz night held after dinner on Wednesdays is a weekly staple. Your HF Holidays leader may be around for tips on guided and self-guided waking routes as well as visit-worthy local attractions.

Walks talks 
Our HF Holidays walk leaders host guided walking information briefings before dinner on guided walking holiday arrival days. This is followed by a group Walks Talk for information on the following day’s guided walks (held before dinner every evening). Self-guided walking guests are, of course, welcome.  

The walking day
Prior to setting off on guided 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. 

Check in & check out

You are welcome to check in from 4pm at the earliest. HF Members can check in earlier, from 2pm. 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. Check out 10am.

•  43 well-appointed guest rooms  •  Exclusive occupancy: 61 guests minimum •  Check in from 4:00pm • For members check in from 2:00pm • Full-board (including cream tea on arrival)  •  Free Wi-Fi  •  Free on-site parking  •  Boot room and drying room  •  2 travel cots & 4 high chairs  •  Discovery Point offering a wide range of local area maps, route guides, and information for self-guided walks  •  Books and games to borrow  •  Licensed bar  •  Three lounges  •  Garden  •  Electric vehicle charging point - Please note, you will need to bring your own cables to use this EV charging point Visit England - Guest Accommodation 

Seasonal dining, tailored for you

Our team of skilled chefs design our dinner menus to showcase the best of each season, from warming winter comfort food to vibrant summer dishes, including vegetarian, vegan  and high-protein options. We also source fruit and vegetables within a  40-mile radius of each house, open every break with a Chef’s Special menu inspired by dishes and flavours of the local area, and are able to adapt dishes to suit special dietary requirements.

Welcome Cream Tea

What better way to start your stay than with a cream tea, served fresh on arrival to make you feel instantly at home.  A quintessentially English tradition, our scones are baked in-house and served with preserves and clotted cream, providing the perfect opportunity to meet fellow walkers.

A hearty breakfast to start the day

Start the day with a freshly-prepared cooked breakfast  and a wide choice from our continental buffet, including  hot drinks, juices and fresh fruit. Our team offer a quick  and friendly service, leaving you fuelled and ready for your day’s adventures.

Our famous picnic lunch

Our personalised picnic lunches are perfect for a day out walking, ready to enjoy when hunger strikes. Choose from a large selection of fresh sandwiches and salads, freshly baked cakes and snacks, including the ever-popular Freddos chocolate bar! Everything is designed to fit neatly into your rucksack, and all of the packaging we provide is recyclable or compostable.

3-course evening meals

Our à la carte evening menus feature a wide choice of starters, mains, and desserts, made with seasonal ingredients and, wherever possible, herbs and vegetables from our own gardens. Shared around sociable tables, dinners are relaxed occasions, with drinks available to order at the table or from the bar, and a traditional Sunday roast to round off the week.

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.

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.

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. For members check in is available from 2:00pm (2026). 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 

*Please note, pool opening hours are: 07:00am – 09:00am and 16:00pm – 18:30pm

For accessibility and assistance information, please contact our expert team on 020 3974 8865 or view the accessibility information online for Freshwater Bay House

View more details View holidays here

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Carbon Footprint

Carbon Footprint - 168kg CO2

We see it as our responsibility to minimise our emissions, not just for this year but every year to come. Our work with sustainability experts, ecollective, has enabled us to measure our carbon footprint and create a strategy to reduce the carbon intensity of our product by 5% each year. Our ambition is to be net zero by 2040 – earlier if we can.

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Dates & Prices

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.

Back to dates

Sat 23 May – Sat 30 May 2026

Trip Note Download

Land Only

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Single Price - Land Only

Members

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Non-members

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Single Supplement

Members

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Non-members

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Itinerary: 7 Nights - Guided Trail

Trip Type: Guided trails

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.

All holidays are subject to availability. Supplements may apply.

Sat 13 Jun – Sat 20 Jun 2026

Trip Note Download

Land Only

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Single Price - Land Only

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Single Supplement

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Itinerary: 7 Nights - Guided Trail

Trip Type: Guided trails

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.

All holidays are subject to availability. Supplements may apply.

Sat 26 Sep – Sat 3 Oct 2026

Trip Note Download

Land Only

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Single Price - Land Only

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Single Supplement

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Itinerary: 7 Nights - Guided Trail

Trip Type: Guided trails

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.

All holidays are subject to availability. Supplements may apply.

Sat 24 Oct – Sat 31 Oct 2026

Trip Note Download

Land Only

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Single Price - Land Only

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Single Supplement

Members

Call to Enquire

020 3974 8865

Non-members

Call to Enquire

020 3974 8865

Itinerary: 7 Nights - Guided Trail

Trip Type: Guided trails

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.

All holidays are subject to availability. Supplements may apply.

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020 3974 8865

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Book with confidence

If the flights we have organised are cancelled or changed, we’ll do everything we can to find alternative transport, with minimal disruption to your holiday

If we cancel your holiday, we honour all refund requests 

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Travel with confidence

We know that peace of mind is priceless, so we’ll always go above and beyond to meet – and exceed – expectations

If the flights we have organised are cancelled or changed, we’ll do everything we can to find alternative transport, with minimal disruption to your holiday

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HF Holidays

A British heritage brand with 111 years of experience

Offering a choice of over 260 itineraries in nearly 40 countries

Run as a co-operative with 40,000-plus members

Image

Book with confidence

If the flights we have organised are cancelled or changed, we’ll do everything we can to find alternative transport, with minimal disruption to your holiday

If we cancel your holiday, we honour all refund requests 

Image

Travel with confidence

We know that peace of mind is priceless, so we’ll always go above and beyond to meet – and exceed – expectations

If the flights we have organised are cancelled or changed, we’ll do everything we can to find alternative transport, with minimal disruption to your holiday

Image

HF Holidays

A British heritage brand with 111 years of experience

Offering a choice of over 260 itineraries in nearly 40 countries

Run as a co-operative with 40,000-plus members

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© 2026 HF Holidays Limited. Registered in England, number 5713R. VAT Number 125 4899 87. All Rights Reserved.

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