Racing

Established in 1987, Windward Sailing began as a yacht charter company run by passionate sailors. In those early days, we quickly realised that many cruising guests were looking for something a little more exciting — so we introduced individual race crew opportunities aboard our yacht Backlash, and now our current race yacht, Incisor.

Today, we welcome sailors of all experience levels to join us for thrilling racing events — from short Solent day races to major offshore challenges like the Rolex Fastnet Race, and everything in between.

Our friendly, competitive atmosphere and expert guidance create an unforgettable experience that keeps crew members coming back year after year. Whether you’re learning the ropes or honing advanced racing skills, Incisor offers the perfect platform for performance sailing.

Corporate Sailing

Windward Sailing also specialises in corporate sailing events, providing unique and memorable experiences for companies and organisations.

We help teams participate in prestigious regattas such as Cowes Week and the Little Britain Challenge Cup, as well as tailor-made industry events. Our aim is to deliver maximum value from every sailing experience — whether it’s building teamwork, entertaining clients, or rewarding staff.

A full catering service is available, from yacht provisioning to luxurious seafood buffets, ensuring your event is seamless both on and off the water.

Cruising

For those seeking a more relaxed experience, Windward Sailing offers bespoke cruising adventures designed around your requirements.

Charter a yacht with family or friends and explore the beautiful Solent. If you can’t assemble a full crew, we can organise shared sailing weekends where individuals can join like-minded sailors on one of our yachts.

Every cruising package is flexible, friendly, and focused on providing the best sailing experience possible.

About Us

At Windward Sailing Yacht Charter, we’ve been delivering quality sailing experiences since 1987. We’re always happy to talk sailing — whether you’re planning a race campaign, a corporate event, or a relaxed cruise.

If you’d like advice, have specific ideas, or just want to discuss your next sailing adventure, please get in touch.