Isle of Wight Cycling Holidays

Get on your bike and head to the Isle of Wight for a cycling holiday set within the best of the English countryside.

The Island is often referred to as ‘England in a nutshell’ due to its picturesque towns, villages and stunning landscape, and being an Island just 13 miles by 23 miles in size, it’s not hard to see why it’s earned the name ‘Bicycle Island’.

Take a look at our Bicycle Island pages and view some of the routes the Isle of Wight has to offer.

We have a route to suit every fitness level on every kind of terrain, so you’ll never be short of trails to try.

Day Rides provide cyclists with the opportunity to explore three or four villages in one day and are graded in difficulty level.

Take a leisurely pedal around Ryde and the East side of the Island, or challenge yourself on the hills of chalky West Wight.

The Red Squirrel Trail provides a great route for family groups as most of the cycling takes place on smooth cycleways which have been created from disused rail tracks.

Follow the trail through the countryside and keep your eyes peeled for the Isle of Wight’s shy red squirrel residents!

If you’re visiting for a few days, bring your bike and discover the Island via the Taste Round The Island Cycle Route.

Visit some of the food and drink locations en route to sample some of the excellent local produce the Isle of Wight has the offer.

If you consider yourself a bit of a pro, head west to test your leg muscles on the Chalk Ridge Extreme route.

Witness some of the Island’s most stunning scenery on this mainly road-based route.

If you’d like to take part in guided races and tours, visit the Island at the time of the Isle of Wight Cycling Festival.

Or if you’d like to book a one to one tour, contact one of the cycling service providers listed on our Bicycle Island page.

The Bicycle Island homepage also contains information about baggage transfer and bike hire so you can leave most of the hard work to someone else!

Looking for somewhere to stay?

View some of the Island’s cyclist friendly accommodation.

From quaint self-catering holiday cottages to camping sites and luxury hotels, it’s easy to find your ideal cycling holiday base on the Isle of Wight.