The Isle of Wight has been a popular holiday destination since the Victorian era when Queen Victoria made Osbourne House her winter home. The island is known for its beautiful scenery, especially on the coast, and mild climate. It is also a well known destination for walking with an annual walking festival.

Our walks will explore both the island’s coast and interior providing a varied itinerary and a great way to get to know the island. Our itinerary will include the Needles, the impressive chalk stacks to the west of the island and stunning Freshwater Bay. We will walk direct from Shanklin on one day and hope to head to the beautiful St Helens bay too – a stunning location on the east coast.

On this holiday, we will be based in Shanklin, to the south east of the island. It is a popular seaside resort with a beautiful sandy beach and pretty old quarter. We hope to have sole use of a lovely 4 star B&B, in a quiet residential area of Shankiln, 5 minutes walk from the station and  10 minutes from the seafront. The perfect location for our walking holiday.

The Isle of Wight is less than 20 minutes away by catamaran and 10 minutes by hovercraft. Both options are linked with train services.

Itinerary (subject to change)

Day 1: Arrive Shanklin and check in from 4pm. Meet in the lounge at 6pm for a briefing before walking down to the seafront for dinner.

Day 2: Shanklin Circular A lovely circular route on the Worsley Trail towards Wroxall and St Martin’s Down. We then head up from Wroxall Luccombe and Bonchurch Downs before heading back to Shanklin. A bracing walk with a few undulations and great views.

Day 3: Long Stone and Brighstone We head across the island to Shorwell on the south west coast to begin our walk on the Downs following a different part of the Worsley Trail. Again great views, one or two ups and downs and lovely downland walking. We circle back passing the Neolithic Long Stone and Mottistone Manor to the village of Brighstone.

Day 4: Brading Marshes and Bembridge Today we take the train north east to Brading where we head across the Brading Marshes Nature Reserve. We will then head up to Bembridge Down passing Bembridge Fort before joining the coastal path to the lovely village of Bembridge. Our return journey by bus takes us via Sandown. .

Day 5: Alum Bay, the Needles and Tennyson Down We cross to the west side of the island to Totland where we will start our walk west along the coastal path to the Needles and up onto West High Down and Tennyson Down – fingers crossed for a clear day as the views are spectacular. We finish the walk in the impressive Freshwater Bay.

Day 6: We depart after breakfast for our journeys home.

• Price
• Accommodation
• Grade
• Guide
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Single Occupancy Ensuite £940 Twin Shared Ensuite £150 per person discount If there is nobody to share with, you will be asked to pay for single occupancy and given the option to cancel if this is not feasible. Included in the price: 5 nights' 4 star B&B accommodation; packed lunch on 4 days; transport to walks as required. Not included: travel to Shanklin; dinner (this will be arranged by your guide); personal expenses; insurance.

We have exclusive use of the 10 bedroom Kenbury B&B. An imposing building with garden and bar, it is in a quiet location around 10 minutes walk from the beach. "Our focus is on you, ensuring you have a good night’s sleep in a comfortable bed, a hot shower with quality toiletries and a sumptuous Isle of Wight breakfast. Walkers and cyclists are very welcome and any guests just wanting to relax and unwind, maybe with a drink, can do so in the garden or comfy lounge and bar. We are based in a quiet residential area, less than 10-15 minutes walk to the seafront or Shanklin old town."

Walks are up to 8 miles and will involve some ascent and descent especially on the coastal paths. Expect between 250 and 400m of ascent on most days.  There will be a mixture of coastal and inland walking at a steady pace with breaks to take in our surroundings. You will need to be reasonably fit to enjoy this holiday.

  Your guide for this holiday is Clare Kelly, owner of Her on a Hill. For more information, read on

There are ferries, catamarans and hovercrafts to the Isle of Wight. The easiest crossing for public transport connections is from Portsmouth to Ryde. From Ryde Pier there is a connecting train to Shanklin which is a 5 minute walk away from the hotel. Discount codes are available for the ferries. For further information take a look at: https://www.visitisleofwight.co.uk/travel/isle-of-wight-ferry