On the eve of what is arguably the region’s consensus favorite sailboat race, Round the County, I’m updating an almost-10-year-old editorial exploring why I (and so many other sailors) point to this event as the highlight of the season. 

For many regattas, participation numbers are a fraction of their former glory. Still, there are two events with similar racing formats that draw crowds so large they often sell out: Round the County, co-hosted by Orcas Island Yacht Club and Friday Harbor Sailing Club, and Sloop Tavern Yacht Club’s Race to the Straits.

More than one hundred boats typically participate in each event. Many hundreds of sailors have an awesome time. The registration limit is reached earlier and earlier every year. So, why do these thrive while others struggle, despite the best efforts of good sailors and dedicated volunteers? My answer is something I refer to as the Destination Wedding Principle.

I can remember watching a YouTube clip of Ken Read (top-notch American Volvo and America’s Cup racer) giving a talk at a conference in 2014. Read was beating the drum about prioritizing comfort, fun, and variety in racing, saying that a few hours of racing is the right amount. He was also encouraging a move away from simple windward-leeward courses. I tend to agree with these ideas, and would venture that Round the County and Race to the Straits align with this philosophy, and that it’s a big part of their success.

Our regional distance racing classics require sailing into or through the night. Royal Victoria’s Swiftsure is the most notable, but West Vancouver Yacht Club’s Southern Straits, and the Seattle Yacht Club’s Smith Island/Protection Island Races are all in this mold, with distances between 80 and 150 miles. By contrast, both Round the County and Race to the Straits are two-day mid-distance races with daily ranges of 35 miles or less; and Round the County promises every point-of-sail on the dial. 

Each of these events depart from a sailing hotspot on Saturday, and send the boats on a course through breathtaking Salish Sea scenery. Each race spends Saturday night partying in a quaint and picturesque locale, a destination more than worthy of a visit on any occasion. And I do mean partying, as in nobody goes home, nobody has to take the dog for a walk, nobody’s checking on the kids, and nobody has work in the morning. Partying. That doesn’t necessarily mean alcohol fueled, though we are sailors and for many it does. On Sunday morning of Race to the Straits or Round the County, you pry your eyes open and head right out on the water for another great 30-mile sail home.

It’s kind of the dream, isn’t it? Have you ever left a destination wedding having had a bad time? All your friends are hanging out, and real-world obligations are suspended while you’re in some temporary, far-off utopia. You get to see people you know in a different context, catching up with more people from different boats. Even a rough day on the race course can’t dampen spirits at Race to the Strait or Round the County.

I love those tough distance races—event their freezing overnight watches—and want to see them thrive, too. But, is it as fun as those with an overnight stop? The numbers tend to say no, and so do I. Candidly, the years since Read’s presentation have seen some resurgence of the celebration of challenge—that ease and comfort are one way to fun, and pushing yourself to the punishing limits is another. The point is that even the grit merchants have a ball at Round the County. It can be rowdy, very rowdy, but you turn off the challenge faucet by 6pm at the latest, and you can still make the party.

In the years since I first experienced Round the County and Race to the Straits, I’ve also come to appreciate the cruising adjacency of these regattas. Each is undoubtedly a race, but they have a little bit of that cruise-y magic. As I developed my own identity as a cruising sailor, I found connections between what’s amazing about Round the County and Race to the Straits and the awe-inspiring day-to-day of a cruiser. Still, it’s the can’t-miss moment-in-time with all your pals that pushes these events beyond simply great cruising and into the Destination Wedding zone. At least that’s what I think.

Title background photo courtesy of Jan Anderson.