Dancing it Out on Dogsmile

Articles, Cruising Lifestyle

by David Kilmer

On the final day of regatta, I woke uneasy, escaping a dream in which I was about to go toe-to-toe with some bruiser of a Harley rider I’d offended. My last thought in the dream was a Robert Jordan quote: “Whatever comes, face it on your feet”. I got my bearings, pulled on a shirt with the team colors — Grenada green, red and gold — and caught a roller-coaster dollar bus ride to Port Louis Marina. I saw the skipper, Jon Totten, wearing his own multicolored shirt, taking giant strides toward the docks, holding a scavenged batten.

We converged on our race boat, Dogsmile, a 15-year-old J/105 with red trim. The crew sawed and filed away at the batten in last-minute heroics. In my role as navi-guesser, I put a gauge on the rod rig and took a couple turns off the uppers and one off the mids, anticipating a rare lightwind day.

As we motored out the channel, we considered our dubious prospects. Dogsmile, in her first-ever regatta in our hands, was lying a distant tenth out of 11 in the racing division. On Day One, our first act had been to lose the kite in a hammering squall at the top mark, with photographer Tim Wright a boat length away to document the anguish as we drifted sideways in the rain, trying to haul in our net full of shrimp and shame.

Our second was a crash jibe while hitting the bottom mark, then doing our penalty turn, owing to my blown layline. We’d had some better moments since then, but it wasn’t enough. Our vintage Dacron crackled while the others’ lithe carbon blades lifted quickly away, trailing rotten air. Our new lines kept slipping through old clutches. We were not battle tested.

But our skipper never raised his voice. A Wisconsin farm boy, Jon knows how to put the work in without complaint. He named his boat after a teethbaring neighbor dog, Pepper, that used to frighten him as a boy, until Jon’s dad told him, “He’s just so happy he can’t stand it.” Jon’s life has been all about sharing that same sense of utter joy, as a river guide, backcountry leader, college teacher and now skipper and sailing instructor.

After the first day, when some owners might be excoriating the litany of our sins, Jon beckoned us to the cockpit, and with tears in his eyes, said how much it meant to have us all here, to bring his own boat to this epic regatta. “Your Mom is so proud of you,” someone said, and Jon smiled through the mist and touched the tattoo that said LUANNE next to his heart. She’d known early on he was a different kind of kid, and always encouraged him to chase the broader horizons.

Not long after he lost Luanne, Jon bought his J boat and sailed to Grenada with a purpose. He wanted others to find that same ridiculous elation he felt at the helm of a sailboat. Dogsmile joined LTD Sailing (short for Living the Dream), a Secret Harbour-based company offering sailing schools, charters and boat sales.

As we sailed on through the squalls and calms, thrills and spills, we weren’t always doing the right thing on the race course. (How hard should it be to call a simple layline?!) But we were always doing right by each other, and that’s what counted to Jon. Dogsmile is, above all, a kind boat, thanks to the steady example of her skipper.

Once someone back in “Fantasyland” tried to holler into the wind to the bow crew in “Adventureland.” Jon said quietly, “Nope, we’re not going to do that.”

Jon had read this tiresome article about all the right things the skipper should say between races. He said we weren’t going to do that, either. Good, bad or awful, we were going to dance it out, just like the doctors on Grey’s Anatomy. As soon as the finish horn sounded in each race, the speakers came out, and our brightly colored squad wiggled, fist-pumped and boogied to “Hey-Ya”, “Boom-Shack-a-Lack”, “CottonEye Joe”, “Lose Yourself”, and “Girls Just Want to Have Fun”. From the rest of the boats, who couldn’t hear the music, we just looked daft.

The wind was topsy-turvy that last day. We sailed upwind legs toward the west, an impossibility in the tradewinds. There were times when we were going backwards. For our crew, who cut our teeth racing on Pacific Northwest lakes and bays, it felt like home. The Dogsmile crew, despite sitting at the bottom of the leaderboard, sailed our hearts out. We called and caught every hint of breeze, and tweaked that little boat relentlessly. At several surreal times, we whispered past the big pro boats on crazy angles of sail — say, wing-on-wing holding out the boom with everyone else close-hauled and parked.

When we got back to the dock, other skippers started walking up and congratulating Jon. Turns out, Dogsmile had won a first and a third on the day, and moved up two places in the fleet overall. The stoke was off the charts. We were all dogsmilin’.

So cheers to the captain and crew who kept the fun meter high, heads in the game, voices low and sails full through thick and thin of our very first Grenada Sailing Week… and all with the best dance moves in the fleet.

Cheers to a kind boat, and with a little luck and work, a fast boat too.

Keep on smiling, Dogsmile!

This article was originally published in Caribbean Compass and is being used with express permission from the publisher.