Key West Classic

Race Conditions

This year, the conditions were ideal. Key West has a unique wind-measurement system much like Hawaii has a unique wave-measuring system—5 foot Hawaiian is 10 foot anywhere else. For Key West, 10 miles per hour of wind is 20 miles per hour anywhere else. It just works out that way. (Keep that in mind when you see forecasts.)

Beyond the start of the race which is always amazing to behold, the highlight of course for me was paddling past the crew ships, which are like skyscrapers on their side. The Disney cruise ship had a giant smily face in the front. You could get right up next to them, giving you a real feel for their scale and provided a nice little wedge wave that ran along the hull.

For everyone, it was a grind. I know a lot of people had heat issues, but for all, it was another amazing experience. We battled tons of Sargassum weed. This seaweed for anybody who didn’t have a weedless fin or weedless rudder because a constant issue dealt with by jumping in and cleaning off the rudder/fin. In the Key West heat, that might have helped keep them cool as it did for me.

But the race is such a small part of it all. It’s an excuse to come together, to help, heal, renew

Here are some of the stories from this weekend that really pulled at my heart, inspired me and reminded me of why this paddle community is so amazing, why events like this are so important for so many. Why we paddle. We we line up. And why we finish.

Special Olympics of Monroe County

Every year we get to visit our incredible athletes in Key West who are using their success in sports as models for success in their lives. The coaches and teams are so stoked and work so hard. I nearly lost it when I saw that one of the athletes, Jennifer, was holding her bronze medal from competing in Seattle in paddleboarding at the Special Olympics. She and the other athletes have trained so hard. It was just awesome to see her success, to celebrate such an amazing accomplishment. Every year, the Key West Classic helps raise money for travel, equipment and other expenses for these incredible paddlers.

Key West Classic

Here is Jennifer Averette with receiving an award from the Key West City Commission:

[L to R]: Commission Richard Payne, Mayor Craig Cates, Special Olympian Jennifer Averette, Commissioners Billy Wardlow, Sam Kaufman and Clayton Lopez. from the The Blue Paper

Travis Suit, Crossing for a Cure and Piper’s Angels

Travis gave one of the most passionate and heartfelt speeches at the awards. I had chills and tears as he expressed his outrage and anger at the cost cystic fibrosis has had on the quality of life for so many people, and inspiration and love toward those who are trying to make a difference. They are holding the Crossing for a Cure on June 15th, 2019, a 80 mile paddle across the Gulf Stream from Bimini in the Bahamas back to the Florida mainland. The event was inspired because of the incredible health benefits of the Ocean for those living with cystic fibrosis, a terminal lung disease. Travis Suit’s daughter Piper was diagnosed with CF when she was four years old.

Paddling for Olivia Paisley Strong

My friend Matt Anderson paddled in the Key West Classic to help raise awareness and fund for little Olivia Paisley Strong as she fights Leukemia. If you can help out with anything today, it would go a long way. Donate here


Classic Key West Finish in style

It was mile 12 of 13.whatever and there was a guy sitting down on his SUP, knees up and head in his hands. I paddled over to see if he was ok. I wasn’t sure if he was sick, or passing out. It looked bad. As I got close and started to ask if he was ok a huge cloud of smoke engulfed his head. He sat up, smiling, a lit cigar in his teeth. He hopped up, and started to paddle toward the finish with his lit cigar after 12 miles. I watched in disbelief as he hit the backwash from the pier and fell in. But this smoking ninja grabbed the cigar with his hand as he fell and kept it raised above the water, remounted and kept paddling in classic Key West Style. Aside from the smoke and smell, it was pretty funny.

10-year-old Andy Gribben

This kid slayed it. He paddled the whole 13+ mile course in 4:24:36.09 and finished with a smile on his face. Great day for him, and a great day for his Dad, Ed. So cool to see you both. Nice Quickblade BTW:

Jacqui Woods Kapinowski and her custom Coastal Cruiser

I paddled out to the start of the race with Jacqui. She rows this incredible custom Swift Coastal Racing Shell. It’s amazing and she conquered the rough conditions to finish in a super impressive 03:37:29.99. Jaqui will be rowing her racing shell in the 85 mile trek across the gulfstream in the Crossing for a Cure. 

THANK YOU  to the Lazy Dogs: Soul of the sport

Sue Cooper and the Lazy Dogs have created something completely unique in the paddle world. The setting and the vibe, the inclusive nature where everyone is welcomed and celebrated should be the goal. I’ve paddled this event 5 of the past 6 years and it’s a MUST-DO-BUCKET RACE. Key West never disappoints in its experience and challenge.

Lazy Dogs

Thank you for the loaner board!

Special Thanks to Karen, Bubba and Rob Miller for organizing, delivering and lending me a 14 prone for the race. You always have a loaner board in NC if you need one.

Full 2019 Results:


There are so many other stories, so many people we loved catching up with. We ate sushi cupcakes, had ice cream at Kilwin’s, had tater tots at Jack Flats, rode bikes everywhere. Thanks to Jimmy Terrell who split a room with me and kept the whole weekend fun. Thank you to Sue Cooper, again, for making this all possible. And thank you to Heather Whitehead and the Key West Hospitality Inns for the awesome place to stay.

See you next year…


  1. You make me laugh. So fun to read you…! So refreshing to see how you get of what really matters. Thanks for great article. So great sharing this Key West Classic


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