Recap: 2025 Key West Paddle Classic

The spirit of adventure was alive and well on Saturday, May 10th, as paddlers gathered at Higgs Beach for the 28th annual Key West Paddle Classic. This year marked an exciting new chapter for the beloved event, as Florida Keys Watermans Company proudly took the helm from Lazy Dogs, who stewarded the race from 2013 to 2024. With a legacy dating back to 1997 under the original direction of Michael O'Shaunessy, this iconic race continues to be a cornerstone of the paddle sports community.

A Course Carved by the Sea

The course, just over 12 miles, traced a scenic and challenging path through Key West’s turquoise waters. Starting from Higgs Beach, paddlers headed south toward the Southernmost Point, cut through Key West Harbor, rounded the U.S. Coast Guard base, and cruised under the Fleming Key Bridge. From there, the journey wound through the sailboat mooring field and around Dredger's Key (Sigsbee), then into the narrow stretch of Cow Key Channel — the waterway linking Key West and Stock Island. After a final push past Smathers Beach and the White Street Pier, paddlers returned to Higgs Beach to complete the loop.

The exact direction of the course, as always, was dependent on the tides — a fitting nod to the ocean’s ever-changing nature.

Rough Waters, Steady Paddles

The day began with a Captain’s Meeting and safety briefing led by Matt Sexton, setting a tone of camaraderie and caution. At 9 a.m., the green flag was lifted signaling the start of the race, and competitors paddled out into rolling waves and choppy waters. Despite the challenging conditions, spirits were high and determination ran deep. 

Spectators gathered along the shores and bridges, cheering as racers powered through the channels and pushed toward the finish. 

Community at the Core

As paddlers began crossing the finish line, the celebration kicked into full swing. Florida Keys Brewing Co. handed out cold beers, and Bongo’s Botanical Beer Garden kept everyone fueled with burritos. Laughter, cheers, and high-fives filled the air as racers exchanged stories and shared in their triumphs.

Before the awards ceremony began, the community came together for a silent auction and raffle, with an array of amazing local prizes up for grabs. Proceeds supported the Florida Keys Community Center and gave participants a fun and meaningful way to contribute.

Then came the much-anticipated awards ceremony, honoring the day’s top finishers! Results can be found here. 

Back to Grassy Flats

The day wrapped with a laid-back backyard barbecue at Grassy Flats Resort, where paddlers and families gathered to unwind. The post-race celebration echoed everything the Paddle Classic stands for — resilience, community, and the unshakable love of the ocean.

As Florida Keys Watermans Company embarks on this new era of hosting, the 2025 Key West Paddle Classic reminded us all why this event is so beloved. Here’s to 28 years of paddling tradition — and many more to come!

Want to relive the magic or join us next year? Stay tuned for photos, updates, and early registration details!