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To the uninitiated, all those sailboats cruising along the lake appear to be pleasure crafts savoring a beautiful summer evening in Chicago.

But take a closer look and you can see the boats crisscrossing each other around a constellation of red buoys; you’ll notice the shifting of sails and captains barking out to crew, all hoping to snatch some speed from a quick burst of wind.

No one’s quite sure how it all started, but every Wednesday night most of the city’s sailing harbors host a casual race called the Beer Can Regatta. And although participants have been known to hoist a beer or two afterward, the winners at the North Side’s Belmont Harbor head home with a more nautically appropriate trophy: a bottle of rum.

The prize is a perfect fit for the laid-back nature of the contest, a study in contrast from the more intense sailing that usually happens on weekends–especially during the annual 333-mile Race to Mackinac Island, which started this weekend.

Even among other Beer Can programs in the city, Belmont has a reputation for being the most relaxed race, and the smallest, averaging about 20 boats a week versus more than 80 that compete regularly at Monroe Harbor. Both the Belmont and Monroe Beer Can races are organized and officiated by the Chicago Yacht Club.

But on this evening in mid-July, the Beer Can Regatta is serving a vital role in the development of two students from local sailing school and charter company Chicago Sailing, which operates from offices aboard a Belmont Harbor house boat.

An international pursuit

Captaining a four-person crew aboard the 30-footer known as Bonzai is Irishman John Curtin, 21. One could do worse than spend a Chicago summer working on a sailboat, and that’s precisely what this Dublin law student is doing. An experienced seaman, he has wrestled the choppy waters of the Atlantic. But tonight is his first Beer Can race. He says he has competed in similar races in Ireland, as many harbors throughout the world hold their own versions.

“Every race in Ireland is a Beer Can Race,” Curtin said with a laugh. “Basically, this is a midweek, kind of fun regatta. . . . Get out of the office and have a bit of a race in the evening.”

Curtin knows the odds are stacked against his ragtag group sailing away with the coveted bottle of rum. Many boat owners use these midweek races as tune-ups for the more serious weekend racing, which means Bonzai will be competing against some that have sailed together for 10 or more years.

“I’d say it’s mildly competitive,” said Kristine Edmunds, the Chicago Yacht Club’s principal race officer for the Belmont Station Beer Can Series. “There are four different sections, and they race against similar boats within their section. On a typical offshore race these boats would be handicapped. But here, whoever crosses the finish line first wins. Casual scoring goes on, too, because you don’t want the same people to win every week.”

The scoring may be casual, but no self-respecting sailor wants to come in last. One of the students aboard Bonzai is Dennis Schroeder, 55, of Park Ridge. Even though he started sailing only this spring, he already has been out more than 20 times. An executive coach by trade, he’s supremely confident.

“Nothing competitive ever makes me nervous,” he said. “I love it. I love the adrenaline.”

His fellow student, 24-year-old Ryan Fields, who lives in Printers Row, has been sailing since he was a teenager. But he’s relatively new to Chicago, and the Beer Can Regatta helps hone his skills so he can sell himself to area captains looking for worthy crew. He says that although the marathon port-to-port races like the three-day Mackinac are grueling, the quick-sprint Beer Cans are a different sort of challenge.

“Everybody’s close, everybody’s fighting for the wind. There’re boats all around you, and a lot of things can go wrong,” said Fields. “It’s a lot more casual, but it can be a lot more stressful too.”

A bonus: If someone takes a boom to the head, Fields is also a paramedic in training. For novice sailors especially, the boom (the free-swinging piece of metal attached to the foot of the sail that pivots on the mast) can turn a fun day out on the lake into a massive headache. Teryn Bergo, 24, of Glenview, a Chicago Sailing employee and the fourth crew member, recalls how she once witnessed a simple tacking maneuver result in a very messy bloody nose.

Short-lived practice

Meanwhile, as the boat makes its way about a half-mile out on Lake Michigan, Captain John initiates some prerace practice runs. “Ready to tack!” he yells, and suddenly all hands spring into action to turn the boat into the wind by changing the sails from one side to the other. There’s a flurry of activity, lines (ropes to you landlubbers) fly everywhere as the main and jib sails are released, and then that distinct cranking noise as the sails are winched tight.

But just as the crew is starting to gel, a San Francisco-thick fog engulfs the lakefront. Visibility is reduced to a few hundred feet. An air horn sounds, signaling that the evening’s race has been canceled. A few boats stay out, but with an inexperienced crew, the vessel from Chicago Sailing isn’t about to take any chances.

But this being Beer Can night, the Bonzai crew manages to crack a few cold ones back at the dock, then moves to the nearby Belmont Station Clubhouse bar. That the race was canceled is not only disappointing, but the unexpected break also might cause some to stay out later than usual on a weeknight.

Ordinarily, “When you come in after sailing, between the fresh air and the constant concentration, you’re beat,” said Captain John. “That’s the great thing, after a few beers it’s game over. You’re a cheap date for the night.”

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Where to get your sea legs

Think you need to be rich or have a buddy with a boat to take up sailing? Wrong. According to Alan Veenstra, owner of Chicago Sailing, their goal is to let the average person know the lake is accessible to them.

“The entry barriers are very low. . . . All you really need is a rain jacket,” said Tim Snyder, Belmont Station Beer Can Series coordinator. “There are people that would love to have you if you’re willing to learn, adapt and practice a little bit.” Get started with these local sailing schools still offering summer classes:

Chicago Sailing: Belmont Harbor. $400-$450 for 16 hours of instruction. 773-871-7245, chicagosailing.com.

Chicago Yacht Club Sailing School: Belmont Harbor. $340-$575 for 18 hours. 773-477-6951, chicagoyachtclub.org.

3rd Coast Cruising: Monroe Harbor. $290 for nine hours. 866-724-5373, 3rdcoastcruising.com/SailFitness.html.

Columbia Yacht Club Sailing School: 111 N. Lake Shore Drive. $500-$700 for 18 hours. 312-938-3625, sailcolumbia.com.

Northwestern University Sailing Center: 1823 Campus Drive, Evanston (just north of Clark Street Beach). $279 for 20 hours. 847-491-4142, www.fitrec.northwestern.edu/classes/aquatics/sailing.html.

–R.O.

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q@tribune.com