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Women of the Sea
In Milwaukee, Mary Ann is the skipper. By Arlene Becker
Photo by Kat Schleicher

Fifty-year-old Wendy Olsen is a cultured, willowy extrovert who stands 6-foot-2 in Italian stilettos, kisses her friends affectionately with light pecks on their cheeks, and salts her speech with ciao and Italian terms of endearment.

She’s equally graceful while shouting maneuvers during a dead-even race as her 34-foot Peterson sailboat, skimming the waters of Lake Michigan, tacks, comes about and jibes.

The agile Olsen is one of 25 female sailing skippers registered in this city, notable for its strong cadre of female racing captains. According to former America’s Cup captain Dawn Riley, Milwaukee is unique for its concentration of women who lead racing teams. Women make up some 12 percent of the racing skippers registered at the Milwaukee Yacht Club, whereas nationally, female captains are about half as common, says Riley. But women everywhere have made inroads into sailing, which has traditionally been dominated by men. “In racing, in particular,” Riley says, “it is unusual nowadays to see a boat without women on board.”

Many boats “manned” by only women compete in weekly summer races hosted by the Milwaukee Bay Women’s Sailing Organization. Founded in 1994 by 30 female sailors and a lone male, the organization has grown to 86 members. Presumably, they are like Olsen and appreciate “the camaraderie of a women-only crew.”

The group’s youngest skipper, 19-year-old Whitney Kent, took her first lesson at age 6 and is captain of a crew of seven. “Male crewmen, even those older than her, respect her sailing commands,” says Cheri Kent, the young skipper’s mother.

And other female sailors in Milwaukee share similar stories.

There’s JoAnne “Jolly” Schelwat, 71, whose crew sometimes includes her 88-year-old stepmother, Jean Lindemann, an experienced sailor in her own right.

There’s Phyllis McDonald, 62, the Rosie the Riveter of Milwaukee sailing, who says she “can set valves in both automobile and boat engines.” While ferrying a boat to a race on one occasion, a cooling propeller failed. “There was an electrical issue,” McDonald says, “which I fixed then and there.”

And there’s Helen “Cookie” Mueller, 62, the South Shore Yacht Club’s first female commodore, the title given to the head of the club’s board.

These women and others are scheduled to sail each Monday from June 4 through the end of August, and the Bay Women’s Sailing Organization will hold its second Midwest Women’s Sailing Conference in Milwaukee May 19.

Meanwhile, Olsen will be skimming along in her boat, called Ragtime. A perfect name, she says, “as I like to jam with my horn.” Maybe while wearing a pair of those high heels.

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