Isle of Wight Trails

With 13 by 23 miles of pure Island happiness to explore, it can be difficult to know where to start your Isle of Wight adventure! Luckily we’ve put together some handy trails to guide you along the coastline, through magical woodland or along smooth cycle tracks that go from town to town.

Whether you’re on your bike, on foot or even on a horse, we’ve got the Isle of Wight trail to suit you. Visit all the landmarks on the trail, or just pick a few and take your time making the most of the sights and sounds of the Island known as ‘England in Miniature’. Click on the thumbnails below to learn about some of our trails.

Cycling Trails

The Isle of Wight has often been referred to as Bicycle Island, and with its amazing variety of cycle tracks it’s not hard to see why. From gentle routes for beginners that meander through the Island’s quaint chocolate-box villages to extremely hilly routes that only the pros should tackle, the Island is well equipped to cater for all ages and cycling abilities.

Walking Trails

The Isle of Wight is a walker’s paradise. With very little distance from town to town, you can see multiple towns and villages in one day of walking! Explore the coast, take a look in the village shops, stop off for some lunch at a beachside café and head back to your accommodation (or hop on the bus if your legs are too tired)!

For information about the Island’s walking routes, take a look at our dedicated Isle of Wight Walking Routes page, or click on some of the thumbnails below to find out more about your chosen route.

Discovery Trails

Some of the points on these trails have a little more distance between them (though not too much), and you could spend a whole day visiting just one or two points on the map. Cycle between the points, or opt to take the car if you fancy giving your legs a rest.

By following these trails you’ll learn a little something about the Island to enhance your stay. The Churchill Trail offers a fascinating insight into the time that Churchill spent on the Island, from his days as a young boy building sandcastles on Ventnor beach, to visiting in his adult life.