Key West: Memories of a Newbie

Greetings, all. I must admit to being a bit distracted today; in order to write this blog post, I had to tear myself away from Walter Cooper’s mouth-watering photos of what’s now called The Southernmost Regatta. Crystal-clear waves, cool boats—there’s no need to geo-tag a Key West race photo.

Sailors of a certain age all think of “Key West” not just as a destination, but as a time-stamp: the event that kickstarted each sailing year. From the late 1980s until about five years ago, Key West Race Week (KWRW) was the place to be in mid-January for any sailor lucky enough to score a ride. Until it all got too pricey and too crowded… and instead we had to somehow make do with Dry-uary.

A year ago, in the midst of my first-ever adult sailing-free winter, Sailing Inc. announced a revitalized annual trek to the Southernmost point in the U.S.A. So today, Walter’s photos are sparking memories of my very first Key West. Which, in hindsight, kickstarted a crucial personal progression: from wide-eyed newbie to both Olympian and novelist. 

Let me take you back to January of 1990.

After an eye-opening week of sailing at the J/24 Midwinters in Miami (and breakfast with Vince Brun most mornings), heading home to shovel snow and feed the woodstove seemed like a very bad idea. A new sailing friend offered a ride south instead, so I climbed into a rattly van and headed to Key West—even though I had no promised ride or place to stay. The adventures of a twenty-something!

According to The New York Times archives, KWRW 1990 was sponsored by Audi—though only as a footnote to the far more important SORC, a twelve-day circuit that combined day racing and overnights from St. Pete to Fort Lauderdale. “The trend in sailboat competition today favors day races and new handicap rules,” Barbara Lloyd wrote in February of that year. “[KWRW] has grown substantially since the first series in 1988.” She claims that 120 sailboats competed, which sounds about right. (Read more in the aptly-named Times Machine.)

Finding my people

I don’t remember Audi’s support, but I will never forget Ted Hood (Junior)’s kind invitation to join his father’s crew onboard Blue Robin. The Little Harbor 48 wasn’t exactly a racing machine, but it did have an innovative roller-furling boom—and a plush interior, which meant I scored my very own cabin. Thirty-two years later, my only memory of the sailing was one fateful jibe; I narrowly missed being carried over the side by the mainsheet—with all other eyes on the boat looking forward. Ever since, I’ve wondered just how long it would’ve taken for anyone to notice I’d gone swimming.

Ted Hood Senior was already past his SORC-winning years, but he set a serious tone onboard that balanced professionalism with realistic expectations. After sailing each day, I boat-gawked and drank beer with all my newfound friends; a few were “hired guns” who sailed full time, but most, like me, were only wishing they did. For all of us, priorities were as crystal-clear as the water out on the race course; not to party so hard that we missed the next day’s dock start. 

Back to the cold white north

I longed to stay in this regatta-focused world, but I’d already reached the southernmost point—and I had just enough money left for a plane ticket home. So when Key West folded up its tent, I regretfully headed north again. A week later, already tired of feeding the woodstove, I called around until I found a ride for the next big regatta—the direct result of all the friends I’d made in Key West. Like catching waves, it’s always easiest to grab your next crewing opportunity while still riding the high of the last one; a truth that survives to this day.

With another regatta to look forward to, I also realized I could escape back to that tropical paradise right away—via my imagination. I began writing a story about a sailor who grumpily returns home to New England’s snow and ice after a not particularly impressive regatta… though it eventually morphed into something quite different. Looking back now, I can see a direct line from that first Key West to my first (unpublished) novel. 

2022, another first?

I’m still friends with many of the sailors I met that week, though no one remembers it as well as I do. Thirty-two years from now, most of the sailors in Walter’s photos won’t remember much of this very first Southernmost Regatta, either. But I like to imagine that on one of those boats, there’s some newbie crew who hitched a ride to Key West—and then was lucky enough to sail with the 21st century equivalent of Team Hood. If so, maybe this year’s event will also help inspire an Olympic adventure, or a novel—or both. 

Thanks to Sailing Inc. for revitalizing such a memorable regatta. And thanks to Walter Cooper for reviving so many visceral memories of my own racing and writing foundations (and for permission to use his photos). Most of all, thanks to both Ted Hoods: you gave me the life-changing gift of belonging, in a world I now call home.

And now, if you’ll excuse me, I’m gonna go drool over the rest of Walter’s images. Meanwhile, do you have any Key West memories? If so, please share them in the comments below, or drop me an email. I read every single one, with gratitude.