It’s not uncommon to spot a rainbow after a squall when the sunshine breaks through the clouds—a marker of hope and fairer weather ahead for sailors throughout the centuries.
If you’re sailing around Chicago in August, though, you might happen upon a lot more than one rainbow on the water. Rainbow Races, an LGBTQ+ sailing organization, will host its third annual Pride Flotilla, inviting sailors with underrepresented sexual orientations to take center stage out on the water for a day.
“It’s one of those things where people see people in their community doing something and realize ‘I can do that too,’ ” says Charles Szymanski, president of Rainbow Races. “Until people know what they can do—until you expose them to things and they see what’s possible—we will never know the potential they have.”
“Every year we did the Pride Flotilla, we’d have people asking to learn to sail. In the beginning I just brought people out on my own boat.” But as demand increased, Szymanski decided it was time to start a sailing school.
“The [Rainbow Races] board said, ‘Let’s add this to our five-year plan.’ I said ‘No, I want to do this in two.’ ” Just months later, he’d secured the donation of a boat for the program.
“I went to US Sailing and said ‘Hey, we want to start a sailing school—an LGBTQ-focused sailing school.’ They walked us through the whole process, it took like six months of paperwork,” he laughs. But at the end of it all, Rainbow Races was home to the first US Sailing-sanctioned LGBTQ sailing school in the country. Launched mid-summer in 2022, the school will be fully operational for the first time this season. And that’s on top of regular programming like Rainbow Regatta Chicago (now in its fifth year), the Pride Flotilla in August, an Earth Day beach cleanup, and essential skills classes like first aid and diesel basics.
Rainbow Races’ mission is not just to welcome beginners and support LGBTQ+ sailors, but to bring more diversity into the sport across the board. Their efforts are an exercise in inclusion that we can all learn from. For starters, Szymanski says, a big part of improving inclusivity relies on outreach: “You have to get off your butt and go places. You have to be willing to step out of your comfort zone and into those communities and engage with them.” But it’s not always as easy as showing up to recruit. Intersecting challenges make it difficult to get people out on the water.
“I often use the trans community here in Chicago as an example. Years ago, a prominent member of that community said to me ‘Our community cannot get into sailing,’ and I said, ‘Why not?’ ” Szymanski remembers. “It led to a conversation about housing instability and higher costs of living due to medical expenses.” With more pressing issues at the forefront, it seemed unthinkable for them to talk about a luxury like sailing.
But what if Rainbow Races could teach folks enough about boats for them to become liveaboards, trading Chicago rent for cheaper slip fees? Szymanski says dispelling myths about who can sail necessitates a creative approach, but if there is a will to get on the water, there is a way.
The real key to the organization’s success, it seems, is asking that one little question: why not? And instead of settling for “our community can’t because it’s cost prohibitive” or “because many of us were never taught to swim,” Szymanski says that working backward to address those barriers first helps open a way to the solution. There’s no diversity panacea; It takes constant attention, consideration, and effort.
The good news is Rainbow Races isn’t alone in its mission to broaden the sport’s reach and give LGBTQ+ sailors a place to feel welcome. LGBTQ+ clubs exist across the country and around the world, including New York’s Knickerbocker Sailing Association, the Chesapeake’s Open Seas Yacht Club, and the San Francisco Sailing Team.
The pathway to change is never easy, but through the united work of Rainbow Races and many other diversity-focused sailing programs, the skies are clearing. There is hope for a better, more vibrant future for the sport of sailing.