The Isle of Wight – 5 of the best circular walking routes

The Isle of Wight (full post on what to do on the island can be found HERE) is one of the nicest places I’ve ever been for walking. Full of gorgeous rolling English countryside and lots of easily accessible walking paths, there are numerous options for walks of various lengths. For the really adventurous, you can even walk the complete way round the island on the Coastal Path, though this takes 4-7 days depending on fitness.

One of the things we really noticed as visitors were that a lot of the walks suggested were one way, but given we were accessing the start point by car they weren’t always helpful as you’d end up somewhere and have to walk all the way back again. We therefore discovered and planned circular walks, and the below are some of the best on the island (for first time visitors like me!).

1. The Coastal Path

Route & Distance: Freshwater Bay – Tennyson Down – The Needles – Alum Bay – Freshwater Bay (7 miles, mainly flat)

Walking route can be found HERE.

The Coastal Path runs the whole way around the island, spanning over 70 miles (110km). You could walk the whole thing, and to be honest you won’t find a ‘bad’ section of the route – the whole way round expect stunning cliff drops and sea views.

However, if you’re visiting the island as a tourist, I think the best section is to walk from Freshwater Bay across Tennyson Down and to The Needles and Alum Bay to take in some of the main sites of the island on your walk. You can then cross back across The Downs for spectacular views all the way across to mainland England and back to your start point.

The full walk took us about 5 hours, which included lots of photo stops for the views, The Needles and Alum Bay with a picnic lunch – and was a great way to spend a day on the island combining walking with sight seeing.

My full write up of the walk can be found HERE.

2. Beach Explorer

Route & Distance: Shanklin – Ventnor – Steephill Cove – Ventnor Down – Shanklin Down – Shanklin (10 miles, mostly flat)

Walking route can be found HERE

This route takes in some of the island’s best beaches (though don’t expect golden sand – they are mostly shingle on the Isle of Wight). The route starts in Shanklin, where you can begin by exploring Shanklin Chine – a narrow, deep ravine with a waterfall and winding paths. From Shanklin Chine follow the Coastal Path to Ventnor and the first of the beaches on the route.

Ventnor itself is a little run down, but the beach is nice with lovely sea views. From Ventnor detour a little from the traditional circular route and follow the coastal path just a little further to Steephill Cove, one of the island’s hidden gems. Here is the perfect spot for lunch in a secluded fishing bay (and a little relax on the quiet beach if you feel like it!).

Then it’s time to head back on to the route, across Ventnor Down and Shanklin Down until you arrive back at Shanklin. This time head to Shanklin beach, your final stop of the day for fish and chips by the sea.

3. Windswept Hills

Route & Distance: Blackgang viewpoint – The Hoy Monument – Wydcombe – St Catherine’s Oratory – Blackgang viewpoint (5 miles, including steep ascents)

Walking route can be found HERE

The walk starts at Blackgang viewpoint overlooking the beautiful sea and cliffs, then there is a steep ascent to St Catherine’s Down for spectacular (very windy) views across the island. The route then takes in the Hoy Monument before winding downwards to Wydcombe and through beautiful woodland. From the valley the ascent back upwards begins (it does feel like a pretty steep ascent, especially at the end), until you reach the spectacular St Catherine’s Oratory and from there head back to the car park.

4. Queen Victoria’s Trail

Route & Distance: Osborne House – Osborne Beach – East Cowes – Cowes – Osborne House (5 miles, mainly flat)

Take in another of the main visitor attractions on the Isle of Wight, Osborne House. This was Queen Victoria’s summer home, and start with a tour of the house before heading out for walk around the beautiful gardens (don’t miss the walled gardens). From there, take a woodland stroll down to Osborne Beach where you can grab a piece of cake and a tea.

From Osborne Beach head back up to the entrance of Osborne House and head in to East Cowes and to the floating bridge (boat) across to Cowes. Cowes is the maritime centre of the island – explore the shops, take a walk on Cowes sea front and take in some of the museums the town has to offer. Then head back on the ferry to your starting point at Osborne House.

5. Heart of the Countryside

Route & Distance: Godshill – Sanham Wood – Freemantle Gate – Appuldurcombe House – Worsley Trail – Godshill (6 miles, mainly flat)

Walk route can be found HERE

Starting in the pretty village of Godshill, visit the beautiful thatched cottages near the church, explore the model village and have lunch in a traditional English pub before embarking on a walk for the afternoon.

From Godshill, follow the winding footpaths in to Sanham Wood and out through to Freemantle Gate, the once grand entrance to Appuldurcombe House. On arrival at Appuldurcombe, detour from the route to actually explore the house’s grounds – once one of the most grand houses on the island, it’s since fallen in to ruins and is now a shell of its former glory making for a quirky place to visit. Once finished at the house, loop back towards Godshill, this time following the Worsley Trail for more glorious views out across the island’s rolling hills and fields.

Thanks so much for reading! There is so much to explore on the Isle of Wight and I hope this walking guide can help you if you decide to explore on foot. Stay safe and happy travelling.


  1. I love the colors of the Isle of Wight; honestly, the grassy cliffs look so clean and smooth, they almost resemble carpets! Looks like the Isle of Wight is the perfect getaway for nature lovers, a way from the city for a weekend break. Thanks for sharing!

    Liked by 1 person

  2. I was so pleasantly surprised by it – it’s definitely less developed than a lot of the UK and for sure is a perfect getaway for nature lovers! Have a great day Rebecca šŸ™‚


  3. Hey Han. You know, one of my favourite things to do is to take long walks around rural or urban neighbourhoods just exploring the views, landscapes, landmarks and attractions. This is a great way for anyone to enjoy their time in Isle of Wight and if I ever visit I’ll be sure to try some of your circular walking paths.



  4. Hi Hannah – we have just returned from the IOW and based on your post we did walks 1, 3 and 5. We loved all 3 of them, and wouldn’t have known about 3 & 5 if not for you post – it’s quite hard to find good circular options. Thank you so much.


    1. Oh I’m so so pleased they were able to give you some inspiration Rosie, that makes doing this travel blog worthwhile šŸ™‚ I hope you had a wonderful visit to the IOW.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s