She’s known as Captain Kelly — one of the few women at the helm of a yacht in Chicago

Kelly Gordon and her first mate, Gianna Mesi, want to take the scare factor out of boating for young women in Chicago.

SHARE She’s known as Captain Kelly — one of the few women at the helm of a yacht in Chicago
Capt. Kelly Gordon, left, and first mate Gianna Mesi

Capt. Kelly Gordon, left, and first mate Gianna Mesi


Kelly Gordon regularly is asked, “Hey, can I speak to the captain?”

“That’s me,” she replies with an amused smile on her face.

Gordon, 39, is the captain of Corporate Retreat, a private 75-foot luxury yacht that docks at Burnham Harbor, just east of Soldier Field, every summer.

“You don’t see a large amount of women taking boats out for fun and even less as working captains,” Gordon said. “I can count them probably on one hand, maybe two.”

Gordon’s first mate is also a woman, Gianna Mesi. The 22-year-old grew up in Park Ridge, lives in Lincoln Park and studies business administration at DePaul University when she’s not on the boat.

Each year, when the weather gets cold, Gordon pilots the yacht out of Chicago and onto a series of waterways, including the Mississippi River, en route to the boat’s winter home in Fort Lauderdale, Florida.

“At harbors along the way, girls come up to us and just want to talk to us about what we do and ask if they can do it, too, and Kelly will often give them a tour of the boat,” said Mesi, who’s headed to the Sunshine State with Gordon and the boat’s chef, Shane Hughes.

“Especially in the South, people look at this chick driver, and they’re like, ‘Come on, really?’” said Hughes, 48, whose previous gigs include a stint as actor Matthew McConaughey’s private chef. “But when she pulls this thing in the harbor and spins it around, there’s a wow factor. And then we get off the boat and people look at me, and I’m like, ‘Nope, that was all Captain Kelly.’”

Gordon grew up on a farm in a small town in Indiana and was working as a chemistry professor at a community college in North Carolina when a student invited her to a party on an 80-foot yacht.

“I said to the captain at the time, ‘I can drive this thing’ — not knowing bow from stern at the time — and the captain said, ‘Come back tomorrow.’ And it took off from there, he took me under his wing,” Gordon said.

The whim led Gordon to change career paths and captain private boats off the North Carolina coast for several years before taking the gig on Lake Michigan three years ago. She looked at Chicago and thought: “It’s new territory, a new challenge, and I’ll be closer to my mom in Indiana.”

She takes every opportunity she can to introduce captaining as a realistic and exciting profession to women and girls.

“There’s a bit of an intimidation factor,” she said. “It’s perceived as a man’s position. It can be daunting learning how to move a large vessel around. ... So I share my story and let other young women know this is something they can do, and I try to inspire them.”

She’s currently guiding a Chicago woman with a background in interior design who reached out for advice on getting into the business.

Earning a merchant mariner’s license requires someone to document their time and work at sea as well as pass a series of Coast Guard courses. Gordon’s captain license lets her pilot yachts up to 140 feet long.

“I grew up with a mom who told me you can be whatever you want to be, and I’ve always had that mentality and that sort of ‘take charge and jump in’ mindset. And I see so many women who want to try, but they’re just afraid to,” Gordon said.

Gordon said she hasn’t faced any negative reaction from her male counterparts in Chicago, only support.

“But if I did, I would ignore it,” she said.

Gordon owns a home in North Carolina but has spent only about three days there in the past three years.

She lives on Corporate Retreat, which has three state rooms and space for the crew.

Corporate Retreat is owned a Chicago businessman who asked not to be named, who loves being out on the water with family and friends, she said.

She takes the yacht out about four days a week during the summer, mostly along the Chicago River, up the Lake Michigan coastline, often overnighting in other cities, and, of course, to Chicago’s notorious waterfront party spot — the playpen.

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