29th Annual Key West Paddle Classic

Join Florida Keys Watermans Company for the 29th annual Key West Paddle Classic! Celebrating nearly three decades on the water, this legendary event traces its roots back to 1997 under the vision of Michael O'Shaunessy. Now in its 29th year, the 2026 edition promises to be one for the books!

Whether you're a seasoned KW Paddle Classic veteran — thank you for your continued stoke! — or this race has been living rent-free on your "bucket list," THIS is your year to make it happen.

Registration is now live on Webscorer — secure your spot before prices go up! Already signed up on Paddle Guru? No worries — we’ll transfer your registration over. 😊

Expect an affordable, challenging course, and the kind of unforgettable waterborne camaraderie that only the Paddle Classic can deliver. We will see you in May - stay tuned for more updates!

Also check out other Sports events in Key West, Workshops in Key West.