The Churchill Trail

Follow the Churchill Trail around the beautiful Isle of Wight and learn about some of the landmark events in Sir Winston Churchill’s life.

Choose one place to visit – or tackle the whole trail – and explore the diverse landscape that was inspirational for the wartime Prime Minister. It’s a perfect opportunity to step back in time and enjoy this ‘England in miniature’, cast adrift of the mainland on the other side of the Channel.

You’ll discover one of the best beaches in the World, a serene nature reserve that was once a thriving harbour, and a grand seaside palace belonging to Queen Victoria. Along the way, you’ll also see a magnificent medieval castle that imprisoned a King, the world-famous Needles at Alum Bay, and stylish Ventnor – a jewel of a town that’s built on Mediterranean style terraces and has a unique microclimate.

As you will see, there are statues and monuments around the Island to commemorate Churchill. A beauty spot has even been named after him – Churchill Chine, near the tranquil village of Brook on the stunning south-west coast.

For some relaxed time out, stay at a characterful country pub, a cool campsite surrounded by peaceful nature, or a boutique B&B with super-comfy beds – and enjoy a delicious breakfast before setting off for the day.

Churchill’s experiences were influential in making him the great leader that he was. How will your trip to the Island influence you?

Click on the picture below to get the map and start following in Churchill's footsteps!