On the East Coast, West Coast, and Gulf Coast…on the Great Lakes and all the little lakes and rivers, too—most American sailors have been wooed at one point or another by the siren call of an occasional low-stress, mid-week race. (OK, perhaps it was the skipper’s promise of beer and burgers afterwards.) These informal “beer-can chases” are a great way to break up the work week and inject some on-the-water activity into an otherwise dry weeknight.

We assigned two writers the burdensome task of sailing in weeknight races to see how two hotbed sailing towns, San Francisco, California, and Marblehead, Massachusetts, might differ. Editor-at-large Kimball Livingston tackled a casual Friday night race on the West Coast, while Senior Editor David Schmidt stepped aboard a J/105 for a majestic evening of racing on Massachusetts Bay. We figured this story would yield “tales of two cities,” but the longer our guys were on the case, the more we realized that sailors are sailors, irrespective of place.

In just one beer-can race on Seeya, I witnessed more hilarity than I’ve seen on a boat in a long time, most of it after we realized we were totally screwed. The current was building, the breeze was dropping, the sun was setting and we were applying the appropriate amount of stress. We were laughing. We had drifted past the leeward mark how many times now?

Casual evening races are an opportunity to unwind. You try your darnedest to sail fast because that’s what sailors do, but there’s not much caring about the outcome as long as everybody’s laughing. It was Friday, 5 June. The hour was running toward 2030, and we were part of a tradition going back decades on San Francisco Bay and around America. Corinthian Yacht Club, on the north side of my local pond, is one of 17 outfits along our urban shoreline staging these so-called beer-can races; my compadres can sail and race most any Tuesday, Wednesday, Thursday, or Friday night during the summer. Consider that our wintertime racing also leans toward the casual and purely for fun—and includes our biggest fleets—and you might think this formula actually works.

Mark Thompson, a past commodore at Corinthian, knows that Seeya, his Catalina 380, is no world-beater. As the after-work crowd gathered for the race—some from the harbor, others from elsewhere—we watched as a racy Express 27 was launched from the hoist off Seeya’s stern. Thompson mused, “Years ago I gave up my own Express 27 for a daughter. When she got old enough to discover sailing, it was time to buy another boat, but something with a bit of comfort.” These races work for him because, “It gives the sailing a purpose, and the camaraderie is good. It’s a great way to teach because people learn more by racing. And it’s already scheduled; you don’t have to make it up.”

Thompson wasn’t going to lower his Catalina’s dodger for a Friday night race. He wasn’t even going to put himself and wife Patty and their friends through the paces of setting a spinnaker, though many boats do fly spinnakers in this wonderfully mixed fleet.

So by the power vested in the author, I place us now on the starting line, where we found some J/105s, a Santana 22, a Cal 20, a custom Schumacher, an Alerion 28, a Melges 32 (with 10 people onboard), a shiny new Santa Cruz 37, a Beneteau 36.7, an IOD, a know-it-to-love-it Knarr, an Eight Meter, more Catalinas, some Hunters…oh, and a Swan 51 named Beowulf. And, yes, heads had turned as Paul Cayard and Austin Sperry came walking down the dock to board Beowulf.

I know Cayard well enough to understand that his competitive instinct doesn’t have an off switch, but I also know there’s a difference between game face and Game Face, and this was all about grins.

The fleet assembled in Raccoon Strait, between Angel Island (a state park) and the Tiburon peninsula. Away across the bay rose the hills of San Francisco. For once, it looked pretty mild over there on the city front where, often, Wednesday night woodies and Thursday night kite racers see 20 if not 30 knots of wind.

In the unique layout of the bay’s microclimates, the city front lies directly under the maw of the Golden Gate wind funnel. Raccoon Strait lies under the protection of the Marin County headlands, which blunt the breeze. The denizens of “Marvelous Marin,” as they like to call it (they’ll pay in the next life), often walk around in the evening in their shirtsleeves, looking south at a city buried in fog. Today we had to wonder: With an upper-level trough troubling the pressure gradient, would the sea breeze hold to the finish?

The race committee likewise wondered and chose to send our non-spinnaker division on their basic course: a reach out into the bay and a reach back to a buoy to leeward of the start/finish line, then home to the tune of 200 meters or so. Simple, but the race had its evolutions.

First, there was the matter of crossing the start line. We were right at the transition between ebb and flood tide currents—with us or against us—and when the puffs powered us up we were laying the pin end of the line. When the puffs petered out and the building flood dominated, we were not laying the pin. A lively discussion ensued. We crossed. Then came the complexity of optimizing our heading as we worked puffs, lifts, and headers against a current that would always be against us now, but to varying degrees. A little up. A little down. Medium-fast forward. Medium-slow forward.

By and by, the legends of Seeya emerged. There’s the dedication of Marty and Rochelle Thamm, who drive an hour each way to make the races. It’s worth it, says Rochelle: “Sailors are fun to hang around with and these races are a perfect way to get introductions. I took a women’s sailing seminar here, and I didn’t know much, and Mark took a group of us out. He said, ‘We sail every Friday. Just start showing up.’” Then there’s John Arens, who related how the accidental discovery of a can of Tecate beer led new crew to assume that the skipper was a fan, so everybody for every race brought a fresh supply until one day—after months of mutual suffering—they all agreed, “We hate Tecate!”

Every crew deserves a running joke, so, next time, I’ll pack Tecate.

You know already that things went screwy for us around the leeward mark. Still, we had arrived with good breeze. “We came in like a bullet” became the laugh line of the moment as we turned the mark and stalled and stuck, and Thompson told how, on a previous Friday, “The wind dropped out, and I slipped the key into the ignition, and that’s when the breeze came back. We won that race.”

Darkness was gathering, and along about then I got chilled enough to put on some fleece, which started a trend. We hung on, hoping to repeat the triumph.

There were boats that had started ahead of us, already across the line and dropping their sails. Ashore, as we knew, dinner was cranking up—a choice of serve-your-own stroganoff or grill-your-own burger. The sun dipped behind the peak of Mount Tamalpais, 2,571 feet above sea level. The temperature dropped another notch, and Thompson said, “I feel a key coming on.”

But a puff puffed up. We trimmed and sailed. The puff huffed out. We slipped backward. Thompson teased, turning the key for a pre-ignition beep without actually starting the engine. The breeze did not respond.

Time passed. The temperature dropped another notch.

Thompson beeped the ignition again. The breeze did not respond. This time Thompson announced, “I’m hungry,” and the engine rumbled to life.

We came in like a bullet. The stroganoff was great.