Isle of Wight Bank Holiday Walking Break
Enjoy a relaxed and sociable three-night walking holiday exploring the Isle of Wight, based in a comfortable seafront hotel in Sandown. This fully guided, car-free experience allows you to arrive easily as a foot passenger, with all transport included once you arrive.
Over four days, we explore dramatic chalk cliffs, coastal trails, quiet estuaries, and traditional seaside towns. From iconic landmarks such as The Needles to hidden corners of the island rarely seen by visitors, each day offers rewarding walking balanced with time to pause, enjoy the scenery, and share the experience with fellow walkers.
This is as much about the people as the place — shared walks, meals together, and the easy conversations that naturally develop over the course of a few days spent exploring together.
The Basics
Experience Type: Weekend & Short Breaks
Duration: 3 nights
Accommodation: Hotel
Group Size: Maximum 8
Level: Leisurely Plus
Age: 18+
Dogs: Trained Assistance Dog Only
Booking Calendar…
Explore the Isle of Wight: Coastal Walking and Shared Experience
The Isle of Wight offers one of the most varied and rewarding walking destinations in southern England. Within a relatively small area, the island combines dramatic cliffs, open downland, quiet estuaries, historic harbours, and traditional seaside towns.
This trip has been designed to showcase the best of the island while maintaining a relaxed and sociable pace. Each day’s walk offers variety, interest, and time to enjoy the surroundings, whether that means pausing to watch seabirds riding the coastal winds, enjoying lunch overlooking the sea, or stopping in a harbour town for tea.
Travelling as a small group allows friendships to develop naturally. Many participants join on their own, and the shared experience of walking, eating together, and exploring new places creates a friendly and welcoming atmosphere from the outset.
As part of our car-free collection, all transport once you arrive is included, allowing you to focus entirely on enjoying the experience without worrying about logistics.
Is this trip right for me?
Most people on our trips come on their own
Groups are small, friendly and fully guided
Walking is at a steady pace with regular breaks
There’s no pressure to be super fit or super chatty
If you’re new to Large Outdoors or unsure whether this trip suits you, our Start here page explains how our walking and wild swimming trips work and what it’s really like to join.
Find out more before booking:
https://www.largeoutdoors.com/new-to-large-outdoors-start-here
If you’d prefer to ask a question first, you’re very welcome to get in touch.
Suggested Itinerary
Here’s what we’ve got planned - of course, we may have to offer alternatives or make amendments if the weather misbehaves or other unexpected situations arise!
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Your trip begins with collection from either East Cowes Ferry Terminal at 14:15 or Ryde Pier Ferry Terminal at 14:45.
On our way to Sandown, we may stop at the Isle of Wight Distillery, home of the well-known Mermaid Gin, offering an opportunity to stretch the legs, learn about local craft production, and begin getting to know the group in a relaxed setting.
We then continue to our seafront hotel in Sandown, our base for the next three nights. After time to settle in and unpack, we may take a gentle walk along the promenade, offering our first views across the English Channel and helping everyone ease into the rhythm of the island.
In the evening, we head out together for our first social meal. This is always a highlight of the first day — an opportunity to relax, share travel stories, and begin forming the connections that make these trips special.
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After breakfast, we travel to the western end of the island to begin one of the most memorable walks of the trip.
Starting at Totland Bay, we follow the coastal path towards The Needles, the island’s most famous natural landmark. These striking chalk stacks rise dramatically from the sea, while high chalk cliffs provide uninterrupted views across the Solent.
Continuing along the downs, the path offers expansive views in every direction, before descending towards the historic harbour town of Yarmouth. With its traditional pier, narrow streets, and relaxed atmosphere, it provides a perfect place to pause before continuing inland.
We then follow the Yar estuary, where salt marsh, open countryside, and quiet waterways offer a contrast to the exposed coastal cliffs earlier in the day.
This is a full and rewarding day of walking, typically around 13 miles, showcasing the island’s most dramatic landscapes.
In the evening, we return to Sandown to relax before heading out for another shared meal.
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Today’s walk explores another side of the Isle of Wight, with routes chosen to suit the group and conditions, typically between 8 and 10 miles.
Options may include walking from Bembridge to Seaview, where wide beaches, quiet coastal paths, and open sea views create a relaxed and scenic route. Alternatively, we may explore the downs and coastline around Shanklin and Ventnor, where wooded slopes meet open cliffs and traditional villages.
Another possible route visits St Catherine’s Point, the southernmost tip of the island, where a historic lighthouse stands above rugged coastline shaped by wind and sea.
These walks highlight the quieter character of the island, where time slows and there is space to enjoy the surroundings and the company of the group.
We return to Sandown in the afternoon, with time to relax before our final evening meal together.
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On our final morning, we enjoy a shorter walk of approximately 5 to 6 miles, often exploring the peaceful countryside and coastal environments of the island’s northern side.
Newtown Creek is a favourite option, with its tranquil estuary, abundant birdlife, and quiet paths offering a gentle and fitting conclusion to the trip.
This final walk allows time to reflect on the previous days, enjoy the fresh sea air one last time, and bring the experience to a relaxed close.
Afterwards, we transfer to the ferry terminals, with drop-offs typically around 15:00.
Essential Information
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Meeting Time:
You can either be collected from the ferry terminals at East Cowes or Ryde (see details below) or make your own way to the hotel to meet the group. Checkin is available from 3pm.Meeting Location:
Premier Inn
Isle of Wight Sandown (Seafront)
1-9 Esplanade,
Sandown
PO36 8LAPlease note there are two Premier Inns in Sandown we are staying at the Seafront venue.
Parking:
There is no parking at this venue. You will need to park at Station Avenue which is a short walk away.Pickups:
This is one of Large Outdoors’ Car Free Experiences - we offer a courtesy Pickup as below:
14:15 We will collect from the Red Funnel Ferry Terminal in East Cowes. For those arriving via Southampton.
14:45 We will be collecting from Wightlink Ferry Terminal on Ryde Pier. For those arriving from Porstmouth.
It is also possible to collect from the Ryde Hovercraft Terminal which will be just after the above Ryde Collection.Public Transport:
There is a train station in Sandown.Finish Time: We aim to finish on the final day between 15:00 16:00 - the exact finish time may depend on the planned/chosen activity, group dynamic, weather conditions, whether the group chooses to grab a coffee or lunch together during/after, etc. If you’ve travelled via public transport, please ensure you book onward travel accordingly (i.e. an open return ticket), to allow for flexibility.
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Accommodation Address:
Premier Inn
Isle of Wight Sandown (Seafront)
1-9 Esplanade,
Sandown
PO36 8LARoom Types:
You can book one of the following options, subject to availability:
Double Room
Single Occupancy Double Room
Shared Male / Female RoomDouble Rooms sleep up to two participants booking together in one king-size double bed - bathrooms are en-suite).
Single Occupancy Double Rooms sleep one participant (king-size double bed, bathrooms are en-suite). -
Included:
Pickup (optional) from East Cowes or Ryde Ferry Terminals - see the Meeting Location & Time section above.
3 nights’ accommodation at The Premier Inn.
Guided walks on 3 days (Day 2, 3 & Day 4).
Travel from the accommodation to activity start points and back, where they don’t start from the door.
A hearty cooked breakfast each morning, prepared by the accommodation.
Complimentary tea/coffee, provided in your room at the accommodation, but please ensure you bring sufficient water bottles or carriers to fill up with tap water and take out with you.
Not included:
Travel to and from the meeting location (but please see the Meeting Location & Time section above for details of the Pickup available for those wishing to arrive via public transport).
Dinner each evening - we’ll book a table to enjoy dinner as a group and you can purchase whatever you fancy from the menu available.
Packed Lunch on Days 2, 3 and 4 - we’ll stop somewhere suitable such as local shop, bakery or supermarket. For you to purchase whatever you fancy.
Any extra (i.e. not mentioned above in ‘Included’) excursions or activities that you may partake in which incur a cost.
Alcoholic drinks - the accommodation has a licensed bar if you wish to purchase alcohol.
Any food, drinks or goods you choose to purchase at any shops, restaurant, pubs or cafés visited.
Travel/activity insurance - we recommend having insurance to cover, at a minimum: cancellation and curtailment; medical and emergency expenses (including repatriation); personal accident; injury and death.
Booking Calendar!
Booking FAQ’s
Can I book with a deposit?
Yes, if the trip is more than 12 weeks away you can secure your place with a 20% deposit. The balance is due no later than 10 weeks before travel. You will receive a series of reminder emails when the balance is due. If the trip is less than 12 weeks away, the full balance is due at the time of booking.
Can I pay in instalments?
Yes – although our system doesn't have a function to do this automatically. If you'd like to split your payments, simply email us (hello@largeoutdoors.com) when you'd like to make a payment. Please don't forget to tell us how much you'd like to pay off the balance and your order number. We'll then send you an email with a secure online payment link.
This map is provided for guidance regarding the general location. For detailed meeting information, please refer to the 'Meeting Time & Location' section.