29th Key West Paddle Classic went full send – 2027 date confirmed, SUP athletes react

The 29th edition of the Key West Paddle Classic brought by Florida Keys Waterman Company wrapped up with a bang, delivering another unforgettable chapter for the longest-running paddleboarding and paddle sport event on the U.S. East Coast. Held on 9 May, the iconic 12-mile waterman challenge once again proved the enduring pull of a true classic – drawing a powerful line-up of OGs returning for yet another edition. For many, it marked yet another return to the start line – joining a deep field of pro endurance athletes alongside first-timers ready to test themselves against the legendary course.

From SUP divisions – including 14’, U-14’ and 3-person relay teams – to prone, OC-1, OC-2, surfski and sea kayak, the event continues to showcase one of the most diverse race fields in U.S. paddlesports. Known for its unpredictable mix of chop, current, wind and heat, the island course remains one of the sport’s most respected and demanding tests.

Photos by Florida Keys Waterman Company

This year also brought a meaningful crossover, with the Crossing for Cystic Fibrosis crew joining forces with the event to connect with paddlers and help amplify their mission – adding another layer of community spirit to an already special weekend in Key West.

With the 2027 date already locked in – Saturday, 8 May 2027 – we caught up with athletes to share their stories – why they keep coming back year after year, what makes the Key West Paddle Classic such a special challenge, and why the wider paddling community should mark the calendar and experience paddling around Key West for themselves.

Steve Miller | Photo courtesy of Steve Miller

Steve Miller, Winner of the 12-Mile Men Division, said:

“This was my 12th time racing Key West – and my 7th win. Huge thanks to the Flying Fish Freedom Pro and QuickBlade Paddles.

The reason I keep coming back is simple: you never know what you’re going to get. It’s one of the toughest races in the US, and if you haven’t done it, you should – for the challenge alone.

A 12.5-mile lap around an island can get tricky fast, with every type of condition thrown at you. You might have the tide working with you on one side and against you on the other. Sometimes you get five miles of fun downwinding; other times it’s relentless side chop if the wind doesn’t line up right. Then, on the lee side, you’re dealing with heat, moving water, and heavy boat traffic.

Every year it becomes both a physical and mental battle – but it’s always a great time. Matt and the entire Florida Keys Waterman Company crew do an incredible job, and I’m already looking forward to next year.”

Kimberly Barnes | Photo by Florida Keys Waterman Company

Kimberly Barnes, Winner of the 12-Mile Women Division

“The Key West Paddle Classic is one of my favorite races because it offers a little bit of everything – long distance, current, wind, ocean, and flat-water conditions. The course is a true test of both your mental and physical ability.

This was the first year with a new start and finish location, and I feel like it worked really well. The new race organizers listened to feedback from past participants and, instead of breaking up the 5-mile (8k) ocean leg, it was paddled as one continuous section. (The race used to start and finish in the ocean.) For some reason, that actually made the course feel shorter.

The flat-water start and finish also changed the mental side of the race, because you knew you weren’t heading back out into downwind or side-wind ocean conditions at the end.

I keep coming back to this race year after year because of the course length and the challenging conditions. The new organizers really made everyone feel welcome and are genuinely excited to see the event continue to grow.

There were three ways to paddle this event: as a relay team, the more protected short course, or the long course. The location itself is unique and beautiful – paddling around Key West is an amazing adventure for sure!”

Jake Portwood | Photo by Florida Keys Waterman Company

Jake Portwood, 2nd Place of the 12-Mile Men Division, said:

“The Key West Paddle Classic is the longest-running race on the East Coast, and it was one of my very first races back in 2009. Ever since, this event has stayed at the top of my race calendar every year.

The course is infamous for its brutal conditions, and it never fails to test every paddler. This year, the wind and chop weren’t too bad, with SSE winds at 12-15 mph and around 2-foot chop hitting you on the left side for five miles out in the ocean. The real challenge this year was the heat – daily highs reached 96°F, with a heat index of 105°F.

But despite the tough conditions, I keep coming back year after year because the vibes are always high before, during, and after the race. The new race organizers, Florida Keys Waterman Company, are really focused on the racers and making sure everyone has a great experience.

And if you’re not quite ready to take on the full 12-mile island course, don’t worry – there are two other course options as well. Hope to see some new faces next year for the 30th anniversary of the KWPC!”

Tricia Lyons | Photo by Photo by Florida Keys Waterman Company

Tricia Lyons of Walk on Water Team – Winner of the 12-Mile Full Send Female SUP 3-Person Relay with Haddy Heathrow and Elizabeth Miller – said:

“The conditions our team experienced changed constantly throughout the course. The opening leg meant grinding it out through ocean-side chop near the channel, before the second section offered the chance to take advantage of some fun downwind conditions. From there, it became a real test of awareness and adaptability – navigating heavy boat traffic, dealing with an eddy under the bridge, and pushing through a steady headwind all the way into the finish.

The atmosphere was filled with excitement and energy, bringing together focused, seasoned paddlers and nervous first-timers all sharing the same experience on the water.

In its 29th year, the race carried the feel of a true Classic – the kind of special event that every paddler should experience at least once, regardless of background or ability.”

Photo by Florida Keys Waterman Company

Tristan Gregory, 4th Place of the 12-Mile Full Send Men Division, said:

“On the start line, I was excited – although the extreme heat definitely made me apprehensive. Nearly 100 racers were about to embark on this legendary lap around Key West, with a huge variety of craft on the water, and more than half of them on SUP.

The sit-down craft started first, followed shortly after by SUP and prone. My goal was simple: stick with the lead pack as long as I could, or at least keep them in sight. A lofty goal considering some of the names on the line were world-class racers like Steve Miller, Kim Barnes, and Jake Portwood.

Steve, Jake, and Jake Graham shot off toward the left, aiming for the faster, deeper channel. Meanwhile, Kim, Steve Bernstein, Alex Somoano, and myself opted for the shorter – but much shallower – route out to the ocean.

The ocean section turned into 4.5 miles of messy side chop, making it hard to link any real runners together. Everyone spread out trying to find the best line. At that point, I was very grateful for Flying Fish’s John Meskauskas recommending a wider 24” board.

Tristan Gregory | Photo by Florida Keys Waterman Company

By the time I reached the corner of Key West, I’d definitely burned out my arms more than I should have, and doubts started creeping in about whether I still had another six miles of racing left in me. Aside from Steve Bernstein, I couldn’t see any of the SUP legends anymore – they’re just too darn good.

We passed the enormous cruise ship in port while dodging boats, jet skis, and all their wake, before entering Fleming Key Channel, where the tide funnels down from the north. I committed to hugging the south wall the entire way through the channel. On the other side, a safety boat greeted me and said, “Easy going from here now.”

Yeah… I don’t think so. What followed was another mile of hard, wind-blown side chop, then a stretch of glassy, stagnant, hot-as-hell – but beautiful – paddling around the north side of Dredgers Key.

Then came the final turn. By that stage, I could barely see anyone ahead or behind me. All that remained was 1.5 miles of relentless upwind. Possibly the longest 1.5 miles of my life, lol. But 12.5 miles later, crossing the finish line and hearing that incredible paddle community cheering and welcoming me in suddenly made it all worth it. I’m very pleased to finish 4th with my setup: Flying Fish Freedom Pro 14×24 paired with the Blackfish Salish 500 paddle.”

Full result boards for all divisions can be found here 

Photo by Florida Keys Waterman Company

Registrations are now open for the 2027 edition

Follow Key West Paddle Classic on Facebook and Instagram

To find out more about Florida Keys, visit floridakeyswatermancompany.com

Follow Steve Miller, Kimberly Barnes, Jake Portwood, Tricia Lyons and Tristan Gregory on Instagram

*Images courtesy of  Florida Keys Waterman Company