Youngest captain with Chicago’s First Lady Cruises is anchored by her love of the job

The last time we saw Diamond Gibbs, then a mother of one and a senior deckhand on the Mercury Skyline Queen, she was keeping an eye on the water to make sure her passengers and other boaters on the Chicago River were safe while enjoying themselves. That was in the fall of 2019.

These days, the West Garfield Park native is at the helm of the boats that are part of Chicago’s First Lady Cruises fleet as the company’s youngest boat captain at age 26.

Gibbs, now a mother of two boys, Kameron, 9, and Zion, 2, has been rocking the four bars on her epaulets, signifying her role as captain, since August 2023. The CFL family welcomed her promotion and growth by inviting her onto one of their vessels and, as Gibbs recalls, 10 people were standing in a circle in the salon waiting for her.

“I’m thinking: What did I do? As I walked up on the boat, I was going to back on out, but I saw the owner, Captain Tim Agra standing there. I was like I can’t back out now,” she says laughing, thinking back to the day.

The group was there to congratulate Gibbs on passing the captain’s course. She said she almost teared up, but kept it together.

“I still wake up every day saying, ‘Yeah, I’m a captain!’,” she said. “Officially having the keys to the vessel, it’s nice. Being a part of the captains meeting is like, ‘I’m there! I finally made it!”

Gibbs navigates the official Chicago Architecture Center River Cruise down all three branches of the Chicago River. Five years ago, her eyes were on the prize of being a captain. Now that she has her captain’s license, she’s working toward getting the keys to all of the cruise company’s vessels, five more to be exact.

And while she’s working toward that, she’s also trying to bring more people of color and more women into the world of boating — people like Attia Gray, a Hammond resident who was serving aboard the vessel with Gibbs as first mate on a sunny April afternoon.

“I actually never did a river cruise before applying here,” Gray said. “But I just feel like the way that these boats look, the care they take, it looked like the best company to choose.”

Gray started on the recreational side of boating before transitioning to the commercial side. She already has her captain’s license, which according to Gibbs, requires the holder to have hundreds of hours and days working on the water. And that’s aside from going to school. The schools have varying requirements to get a license.

Once a captain’s license is obtained, one joins a commercial boating company, which has its own program that pairs potential captains with current captains to train them on how to run a particular ship. Both women agree it’s a process that takes time, and Gray is waiting for a spot to open up in the cruise line’s program. Gibbs said she is one of two female captains, out of 18 total captains, with Chicago’s First Lady Cruises. Gibbs can hardly wait to welcome Gray into the fold to make it a trio.

“Another female Black captain … I’ve been trying to help her get to the same level I’m on,” Gibbs said.

As members of the Ship Masters’ Association, Gibbs and Gray are doing community outreach to get more diversity on the water. Gibbs said she’s reaching out to high schools, clubs and youth groups to recruit more people.

Maritime life found Gibbs when, after a year at Malcolm X College, she was studying to be an emergency medical technician. She needed a job that allowed her flexibility with her young son. When she applied for a job with the cruise line, company officials saw on her resume that she was CPR certified and said, “Instead of working on the docks, how about giving it a try on the boat?” The rest is history. Gibbs has been with the company since 2017.

Gibbs still can’t swim, but she can stay afloat and tread water. She’s contemplating taking swim lessons with her sons. Days before Mother’s Day, Gibbs said juggling motherhood with her full-time job is a bit tough, but she said she wouldn’t have been able to do it without the assistance of her mother and the understanding and support of her colleagues in the company.

“They understand my situation. … I’m still a mom, so I have to be able to take care of the boys and help the company as much as I can,” she said. “Working here is pretty much like my second home. When I’m not at home, I prefer to be at work. I don’t even want to go anywhere else.”

Ninety-minute cruises explore both the lake and the river, and passengers hear information about Chicago’s buildings and history from tour guides. Official architecture tours, on the river only, with volunteer docents from the Chicago Architecture Center are also 90 minutes.

“As the senior female in our fourth-generation family-owned business, I am so proud of the hard work and dedication Diamond invested to become a U.S. Coast Guard licensed captain aboard our ships,” said Holly Agra, executive chairman of Chicago’s First Lady Cruises. “Her commitment to safety first, coupled with her ability to work together with fellow crew members, docents and passengers, demonstrate qualities we celebrate as a company.”

Chicago’s First Lady’s season begins in early spring and ends in November. The year-round, full-time job also entails maintaining the boats in the Dolton shipyard during the offseason. Gibbs is on the team that ensures the wood on the boats is maintained.

Gibbs has made a home for herself on the water, so much so that she’s had offers from other companies enticing her to leave CFL. But Gibbs stands firm.

“I’m very happy where I’m at,” she said.