Scenic Walking Holiday exploring the Isle of Wight
Experience a May Day walking holiday on the Isle of Wight, with our car-free experience including three nights in a seafront hotel with en-suite single rooms, exploring iconic sights like The Needles, charming coastal trails, and historic towns.
Experience Type: Multi-Day Experience
Duration: 3 nights
Accommodation: Hotel
Group Size: Maximum 8
Level: Leisurely Plus
Age: 18+
Dogs: Trained Assistance Dog Only
In a Nutshell:
A three-night adventure: Explore the Isle of Wight’s stunning coastal landscapes and charming towns.
Car-free convenience: Arrive as a foot passenger and enjoy included transport across the island.
Seafront accommodation: Stay in a comfortable hotel in Sandown with en-suite single or double rooms.
Guided walks with highlights: Discover iconic locations such as The Needles and Yarmouth, with walks ranging from 5 to 13 miles.
Book today…
Explore the Isle of Wight: A Guided May Day Walking Holiday
Join Large Outdoors for our first-ever Isle of Wight adventure this May Day Bank Holiday! Over three nights, we’ll explore the island’s stunning coastal landscapes, historic landmarks, and charming seaside towns, all while enjoying the comforts of a seafront hotel in Sandown. As part of our Car-Free Experiences, you can arrive as a foot passenger, and we’ll take care of all local transport, ensuring a relaxing and eco-friendly getaway. With guided walks showcasing the Isle of Wight’s best trails and breathtaking views, this trip promises fresh sea air, good company, and unforgettable memories.
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 adventure begins with a free collection from either East Cowes Ferry Terminal at 14:15 or Ryde Pier Ferry Terminal at 14:45. Once gathered, we’ll head to our base for the next three nights, a Premier Inn in Sandown located right on the seafront. After settling in and dropping off bags, we’ll take an informal wander along Sandown’s promenade to soak in the coastal vibes. In the evening, we’ll enjoy a group meal at a local pub or restaurant, getting to know one another while savoring delicious food.
Don’t worry, you can arrive later if needed, but you’ll need to make your own way to Sandown to meet us at the hotel. From Ryde, there’s a direct train, or if you’re arriving at Cowes, simply take the bus to Ryde and then catch the train. -
Fuel up with a hearty cooked breakfast and buffet before we set off to explore the far west of the island. Today’s 13-mile walk begins at Totland Bay, offering stunning views of The Needles, one of the Isle of Wight’s most iconic landmarks. We’ll stroll along the chalky cliffs to the Needles viewpoint, then follow the coastal path to Yarmouth. From here, we’ll trace the river back to Freshwater, enjoying picturesque countryside and peaceful waterways. After a chance to browse Yarmouth’s charming shops or grab a well-deserved refreshment, we’ll return to Sandown to freshen up for another group dinner.
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After another energizing breakfast, we’ll embark on a walk of around 8-10 miles, exploring more of the Isle of Wight’s natural beauty and cultural highlights. Options for today’s route include:
A coastal walk from Bembridge to Seaview, passing sandy beaches, quiet coves, and beautiful sea views.
A circular route around Shanklin and Ventnor, taking in lush downs, historic villages, and coastal vistas.
A woodland and cliff-top trail at St. Catherine’s Point, with views of the lighthouse and the English Channel.
After our walk, we’ll return to Sandown for our final evening meal, rounding off the day with great food and lively conversation.
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On our final morning, we’ll take a leisurely 5-6 mile walk in the north of the island. Highlights might include exploring the tranquil countryside around Newtown Creek, a haven for wildlife, or a gentle coastal trail near Cowes. Afterward, we’ll enjoy a light lunch before heading to the ferry terminals for drop-offs around 3 pm, concluding our Isle of Wight adventure.
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 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.
A Large Outdoors host/guide to welcome you and deal with the logistics for your experience.
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.
The chance to make new friends and meet like-minded people - Large Outdoors is all about making outdoor adventures sociable.
Pre-event support from the Large Outdoors team - give us a shout if there’s any advice or information you need and check out our Blog for useful articles too.
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.
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Please see our Residential (Walking) Kit List.
The compulsory items are selected for your safety, which is of paramount importance to us at Large Outdoors. Each participant should be carrying the items listed.
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• What level of fitness is needed?
This trip is graded as Leisurely Plus. Click here to see Large Outdoors’ Experience Levels.• Can I attend on my own?
Absolutely. The majority of our participants are solo travellers and adventurers. Plenty of fun, laughter and numerous long-term friendships (and a few marriages!) have begun on Large Outdoors experiences since 2008, so there’s no need to feel worried about your first experience, or indeed trying a new type of outdoor activity, with us.• I am currently on a specific diet / have an allergy - can you cater for me?
Unfortunately, we are generally unable to cater for a wide variety of diets or food preferences due to the nature and cost of our catered trips and/or the use of shared kitchens. However, we can offer vegetarian meals, vegan meals, provide meals with gluten* free ingredients, and/or provide dairy* free meals - these options can be selected when booking. *Please see our general FAQs for more information about dietary options.
This particular experience offers a little more flexibility catering wise, as evening meals are taken at local restaurants, so please contact us if you’d like to check whether it is suitable for your dietary needs.• What transport is provided during this trip?
We offer transport with a Pickup service (see Meeting Location & Time section above) and transfers from the accommodation to the activity start points.• Can I bring my dog?
Dogs are not allowed on this experience, except for trained assistance dogs. If you wish to bring your trained assistance dog, please let us know in advance of booking so we can discuss the itinerary and any activity/equipment/accommodation, and of course additional safety requirements or considerations that may be necessary.
This map is provided for guidance regarding the general location. For detailed meeting information, please refer to the 'Meeting Time & Location' section.