From the March 2021 issue of 48° North.

The key to winning the Shaw Island Winter Classic is often to hoist first and douse last — go big! Racing around an island means there usually isn’t a turning mark, someone just decides that they’ve cracked off enough. Maybe they’ll see another boat with someone tinkering on the foredeck. Maybe they’ll calculate the distance of a competitor and decide that it’s worth the risk. Maybe it will work, and maybe they’ll all get a bit salty.

I’ve been doing the Shaw Island Winter Classic for a long time, and this year I was asked to dish out my secrets on Zoom before the race. Racing in the San Juan Islands has so many quirks that you can’t ever figure it all out, no matter how many times you try. And this year’s race was a classic reminder that, when it comes to these intriguing islands, you shouldn’t necessarily listen to my advice.

The race started on a pretty tight reach with some stinger puffs that were generally headers — not exactly the forecast. Orcas Island Yacht Club has a growing fleet of competitive J/70s. They are well coached, and are bringing in new regional sailors and boats. Six of them raced, and six of them hoisted at the start. Mostly successfully! Some of the PHRF boats hoisted, and had mixed results — getting launched, but also sliding to leeward. This “go big” promoter did not in fact hoist at the start. A cranking southerly was predicted, and it was a light to moderate westerly with wildly oscillating puffs. Starting with a #1 genoa made sense to me.

There was some suffering in Harney Channel after the start, for those going slow and for those getting salty. Ahead in Upright Channel, things looked frothy. Even at a great distance, the water looked white. It was so hard to drop down to a #3 jib in winds that were already light, but clearly we were about to get blasted and the transition looked abrupt. In fact, things did get spicy in the channel and around the next corner toward Friday Harbor. Big boats like the schooner Sir Isaac really sunk their teeth into it, while the smallest boats took a bit of a beating.

The next reason not to listen to me is that I was adamant that the current couldn’t be reasoned with and therefore didn’t matter “just take the shortest distance and hoist when you can.” Nope. Sir Isaac won the race overall and in the doublehanded (DH) division. John and Ann Bailey credit their success to taking the deepest part of the channel and gaining a knot of current out there. The extra distance was worth it. One more lesson learned.

Derek Steere’s custom sloop, Endangered Species, going big!

Turning the corner for the final push, Wasp Pass was as carefree as I ever recall. In the protected channel, the hoist was easy, the tide was positive, and the run was effortless — complete with beverages and tunes. It was nearly a perfect day on the water, with a casual sail back to the dock in West Sound after an early finish. The day ended with sunshine and a campfire up the hill.

When the dust settled, three of the top five boats overall were racing doublehanded. Of all the DH teams, my favorite was a father/son team on the J/70 Smoke and Mirrors. Young Kai Vurno and his dad gave me a run for the money crossing tacks many times in the throes of Upright Channel. Kai seemed to be there every time I tacked, and was not relenting in his little boat and big wind. The top step on the podium went to Sir Isaac, with second place going to Christina and Justin Wolfe on the J/111 Raku. Third overall and (1st in the fully crewed division) went to the J/70 Lift Ticket.

Big thanks to Orcas Island Yacht Club for another great Shaw Island Winter Classic. The north end is just getting fired up! The North Sound Party Circuit will be coming back for a second year, and all are invited. See you up here!