Key West Paddle Classic: Wind, Water, and Relay Wins
Three women. One board. Pushing through the unpredictable waters of Key West together.
The Long Road to Key West
There’s something about loading boards onto a vehicle and driving across Florida that reminds you how bad you actually want something.
The drive from Santa Rosa Beach to Key West is brutal. Around twelve hours on the road, broken into two days because nobody wants to crawl out of a vehicle and immediately paddle race in tropical heat. Trisha and I stopped in Stuart to grab her new board and Orlando for the night before finishing the drive down through the Keys.
By the time we rolled into Key West on Thursday around 4 p.m., we were exhausted, hungry, and completely over sitting in a car. Somewhere around the Overseas Highway, reality sets in that this race is not casual. You feel like you’re traveling to another world.
Our hotel was also the start and finish line for the race, which made logistics easy but also made it impossible to mentally escape what was coming. We got settled, saw some familiar paddlers later that evening, and kept things simple before crashing early.
The drive alone had already taken a toll on us.
Friday Practice and Local Knowledge
Friday became our recovery and practice day.
We slept in, got some food, and eventually headed out onto the water to paddle around the course area near the hotel. One of the best things about the paddle world is that you can travel across the state and still run into people you know.
That morning I ran into Garrett Fletcher, one of the top-performing stand-up paddle racers for years before transitioning into outrigger canoe racing. Garrett gave me the rundown on the course and exactly what kind of ocean chaos we were about to deal with.
While we were practicing, we also met a local paddler named Meg who had raced the event before. She explained how unpredictable the conditions could get depending on wind and tide changes around the island.
Listening to locals before a race like this is survival strategy, not casual conversation.
The Race With a Reputation
The Key West Paddle Classic has built a reputation for being one of the toughest paddle races in Florida because the course can throw everything at you in a single event.
Wind. Boat wake. Side chop. Surf. Cross-current. Head current. Downwind glides if you get lucky.
The full course circles the island of Key West for roughly twelve miles. Some years paddlers get beautiful conditions. Other years the ocean tries to publicly humble everyone involved.
We decided the relay division was the smarter move.
Honestly, that was probably one of our better decisions all weekend.
Meet Evil Knieval
Our relay team raced using one board the entire event: my Flying Fish board named Evil Knieval. The name fit perfectly.
John Meskauskas- owner of Flying Fish Board Co. and board shaper extraordinaire
That board at 14 ft and 22.5 inches wide, handled Atlantic chop, Gulf water, currents, relay exchanges, and three women rotating through conditions without complaint. It earned every bit of its reputation that day.
Atlantic Chop and Gulf Downwind
Saturday morning came fast.
Eli Miller took the first leg of the relay, leaving from the hotel and paddling around the Atlantic side of the island. She handled one of the longer sections before tagging me in for leg two.
My section carried me from the Atlantic side around the western edge of Key West and into the Gulf of Mexico. Mine was shorter, around three miles, but I lucked out with downwind conditions for most of the route.
Downwinding is one of the greatest feelings in paddle sports. You stop fighting the water and start working with it. The board begins to glide with the bumps instead of against them. Timing becomes everything. The ocean rewards you when you stop forcing it.
I definitely got the fun leg.
Trisha Lyons closed out the race through the intercoastal section against current and into a headwind because apparently somebody had to do the hard work.
Three Women, One Relay, One Goal
Two of the relay legs were roughly four and a half miles. Mine was shorter, and honestly, I probably worked less than the other two women. Nobody cared because we worked well together as a team.
That’s what mattered.
We crossed the finish line a little over three hours after starting and ended up ranking in the top twenty overall paddlers for the day. We also took first place in the relay division. After checking prior years’ results, we realized we beat the previous relay team times too. That made the win even better.
More Than Just a Paddle Race
One thing that stood out about the Key West Paddle Classic was how much effort the organizers put into the event itself.
The communication was solid. Safety was clearly a priority. The photography setup was incredible. The awards ceremony actually felt fun instead of rushed. Everyone stayed afterward talking story, reconnecting with friends, and hanging out with the Flying Fish crew and other paddlers we see throughout race season.
That’s the side of endurance sports people rarely talk about.
The races matter, but the community matters too.
People willingly show up to suffer together in difficult conditions because challenge creates connection fast. You learn a lot about people when everybody is tired, sunburned, salty, and still laughing afterward.
Why Hard Things Matter
The Key West Paddle Classic also offers something for every level of paddler. You can take on the full twelve-mile island loop if you want the full challenge. You can do the relay like we did. There’s also a four-mile race option on the inside of the island for paddlers wanting something more manageable.
We didn’t know about the four-mile option ahead of time or we might have considered it, but honestly, the relay ended up being perfect. The drive back home was a long two days, again in the car, but my paddling also improved because of the experience.
Races like this expose weaknesses immediately. They force you to adapt to wind, chop, fatigue, current changes, and uncomfortable conditions without panicking. Every difficult mile becomes experience you carry into the next race and the next challenge in life.
You know what though? You do not grow standing still, you grow by putting yourself in environments that demand adaptation.
That’s one of the many reasons I keep racing and paddling.
Key West Was Worth Every Mile
The Key West Paddle Classic delivered exactly what I hoped it would: challenge, community, chaos, growth, and a reminder that the human body is capable of a lot more than most people allow themselves to believe.
Even with the long drive, the exhaustion, and the heat, the experience was worth every mile.
I’ll be posting videos and race footage on my YouTube channel soon, including clips from the course and moments from the weekend with other paddlers.
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For more on the race, read this article featured in Total SUP. If anyone from Total SUP reads this, you got my name wrong in the article. LOL.