Key West Classic never disappoints

As we looped around the island, over Stock Island and the Lazy Dog Shack,  and lined up for landing just east of Smathers Beach, I could feel my whole being warm. It didn’t matter that it was raining. It didn’t matter that the plane was cold enough to hang meat. It’s a gut feeling. As much sensory as spiritual.

By the time we hit the runway, my phone had lit up with texts

“Where are you?!” and “Are you in KW yet?” Jojo with the QB sprinter sat out front. The van was neatly organized with everything a traveling QB rep could need. Everything has a place. Every place has a thing. When Jojo eventually unpacked, it was like a magic trick, like everything had been dehydrated to pack and upon taking it out into the sun and rehydrating, it multiplied in size.

We picked up Jimmy Terrell after his clinic at Lazy Dog Paddle Shack 5114 Overseas Highway, and headed back to the room. Heather Whitehead, Lazy Dog and all-around awesome arranged a house with Key West Hospitality Inns. The inns are 6 renovated and perfect little houses off Duval Street, which is the main drag in Key West. The Inn had Lazy Dog cruiser bikes ready to go. If you go to Key West, get bikes. Sure there are scooters and rental jeeps, some crazy electric 3-wheeled VW-looking things, but the bikes are the way to go.

The house was a few blocks from some of my favorite places:

Blue Heaven, 729 Thomas S which has the most insanely amazing breakfast and enough chickens running around to fill up your “I’m in Key West” Facebook gallery.

I never get in there. It’s always packed. So what’s become my absolute breakfast favorite is La Creperie across the street at 300 Petronia St #1. The coffee is strong and the crepes are insane. They have warm croissants with jam and you can sit at the bar pretty easily and watch the hypnotic art of making crepes.

Just down Duval Street is Jack Flats at 509 Duval St, which has all the hockey and basketball playoff games you’d expect for the beginning of May. Sweet potato fries, good burgers. I don’t know how, but it seemed like everyone was ordering and loving the pot roast. Go figure.

For those not looking for pot roast, perhaps a more organic experience, mostly vegan but with some amazing omnivorous options, there’s the Cafe509 Southard St. It’s not the most creative name for a cafe, but don’t let that fool you. The food is delicious, clean, and the portions are solid. You will leave yelling Kale Yes! Or for Larry Cain, TACO TACO TACO.

The Race

Key West is simply one of paddling’s most historically-rich, enjoyable, challenging and competitive venues. But it isn’t the course. It’s not even the island. It’s the people. From the top down, this event pours stoke and love down upon it’s participants. Sue Cooper, owner of Lazy Dog fosters and cultivates a community of joy and acceptance. Come as you are. Race what you race. Help raise money for Special Olympics South Florida.

Nothing is more soothing than the warmth of the people, sun, and water coming off this beat-down of a winter.

Then they start the race.

The lineup was nuts, but it always is. I made sure to be out there early, because each year I seem to be hurried to get to the line. Not this year.

The start felt amazing. The energy of a race start of this size is palpable beyond the sounds. You can feel it wrap around you and carry you into a sprint, down the coast. It lifts you up. Then, you come around the corner into a sargasso island and 20 mph headwinds against a bulkhead. But that’s what you sign up for in Kew West. It’s supposed to be hard. In the first couple of years, paddlers would come off the water and cry out of exhaustion, accomplishment. And while many of the veterans are used to this, perhaps even consider the race a mid-distance rather than endurance event, it’s hard. And it’s worth every flip, huli, bump and wave.

The section from Mallory Square through the harbor around the KW Special Forces base and under the Fleming Key Bridge was like paddling in a fun house that was being rocked back and forth on a boat being hit by coconuts in a tornado. It ATE ME UP. People were dropping left and right. OCs and surfskis flipped. I heard quite a few expletives. I also heard some classic Lieutenant Dan yells. Some people eat it up. Some people get eaten. That’s Key West. By the time you’ve crossed between Key West and Stock Island and can see the Atlantic again, you’re either relieved to see the wind shade, or just relieved because you know Higgs Beach is so close you can almost hear the Lazy Dogs screaming.

This year, they changed the awards to follow the event right there on Higgs Beach and it was a great change. I’ve loved every year, but it allowed us to hang out more afterward and talk, hear the stories of paddlers having to begrudgingly carry their surfskis back to the start, Coast Guard over-rescuing an OC in a Tea America way. Then there were the success stories. The ones who found a way. The ones how excelled. As always, it was an honor to step into the water and hobble across the finish.

It’s a bucket list. Check that box next year. Use the Paddle Monster 100 Paddle Challenge or Lazy Dog to arrange a board loaner. Bring friends. Hurricane Irma may have knocked them down, but you wouldn’t know it. The locals can see the damage, but to visitors, Key West is Key West. Most visitors will treat the island as a stationary cruise ship— a place for bachelor and bachelorette parties, reunions and weddings. A place to submerge your head in a fishbowl cocktail. But for others, who step out of the plastic tourist scene, the town is rich with local flavor, real things. Like the difference between a cup of waffle house coffee that says 100% columbian and a Cafe Con Leche at Sandy’s Cuban. The Key West Classic offers you a way to see this town with locals, to be guided and introduced to the real Key West. Granted, Duval Street is real. The fun is real. The escape is real. The hangover for some is real real. But use this event to find the soul of this magic town. That’s the energy we tap into. That’s why we keep coming back.

Special thanks to David Rush who was kind enough to lend my an OC. I love that Ehukai. I couldn’t have come to KW without it. Thank you to Heather Whitehead for helping us with a room at the Key West Hospitality Inns. Thank you to Jojo and Jimmy at QuickBlade for lending me a 11o V-Drive paddle for the race. And thank you to the Lazy Dogs who are simply the most wonderful and gracious hosts you can find. And when you go to Key West, they should be your first stop, not just for paddling, but for everything you need to know about and do in Key West.


Womens’ Elite Top 5 SUP:

  • Seychelle 02:20:19.56
  • Terrene Black 02:23:03.22
  • Stephanie Shideler 02:24:24.71
  • Kimberly Barnes 02:26:20.38
  • Maddie Miller  02:35:07.55

Mens’ Elite Top 5 SUP:

  • Enzo Bennett 02:04:20.13
  • Eri Tenorio 02:07:10.96
  • Larry Cain 02:07:25.62
  • Garrett Fletcher 02:08:43.27
  • Steve Miller 02:09:19.00


  • Murray Hunkin 01:50:39.38
  • Chris Vincent 02:12:33.42
  • Lisa Hertz Malick 02:16:17.07
  • Anita Allen 02:16:25.68


  • Jamie Twigg 01:56:47.65
  • Jason Geiger 01:58:25.54
  • Matt Kearney 02:01:17.80
  • Paolo Ameglio 02:05:12.51
  • Darian Hildreth 02:05:37.09


  • Dustin Bumgardner Unlimited 02:21:45.57
  • Chris Cannavaro Unlimited 02:35:44.36
  • Steve Barnes  Stock 02:43:22.78
  • Daniel Prosser Unlimited 02:49:51.81
  • Karen Figueroa Stock 03:02:18.68

Full Results can be found here at Paddle Guru