Second City Sisters To Bless The Fleet At Rainbow Races’ Annual Regatta

LOOP — The nation’s only officially sanctioned LGBTQ+ sailing school, which is based on the South Side, is hosting its annual regatta on Lake Michigan this weekend.

Rainbow Races‘ seventh annual regatta is Saturday at Columbia Yacht Club, 111 N. DuSable Lake Shore Drive. It’s the regatta’s first year at the club.

The race — which will involve dozens of yachts and their crews — serves as the largest fundraiser for the organization, which hosts a school for U.S. Sailing keelboat certification and “first experience” sails.

“We are looking to expand a little bit, both in types of classes and boats we have,” Vice President Charles Szymanski said. “We just got a boat donated to us in the fall of last year, so we’re looking to raise money to put that boat in the water and keep the price of classes low.”

The festivities begin 11:30 a.m. with a blessing of the fleet performed by the Second City Sisters, the local “mission house” or chapter of the Sisters of Perpetual Indulgence. The group of queer and trans “nuns” advocates for safe sex and sex positivity while fundraising for LGBTQ+ organizations.

“Rainbow Races is an organization that’s trying to open up those doors, break down those walls and serve the LGBTQ community,” said Sister Hooda Thunkett, abbess of the Second City Sisters.

“It’s in total alignment with what we’re trying to do [alongside] the organizations we partner with. … We’ll bring some lighthearted joy and fun to this event and celebrate the way of the water.”

The race begins 1 p.m. and will follow a course to be determined the day of, based on wind direction. Navy Pier is likely the best place from which to watch the race, and viewers should bring binoculars as the course will likely take sailors several miles offshore, Szymanski said.

The race is followed by an afterparty at Columbia Yacht Club, featuring the “Rainblow Regatta” — similar to the Cub Scouts race in which contestants race model sailboats by blowing on the sails — a DJ and games.

Tickets for the afterparty are $45 per plate. To buy tickets, click here. To donate to Rainbow Races, click here.

The funds raised through the regatta can help Rainbow Races avoid class price increases, while the group aims to start a scholarship program with continued fundraising and corporate sponsorships, Szymanski said.

“We cater to the LGBTQ+ community, but also focus on bringing traditionally disenfranchised folks out to sea,” Szymanski said. “We want folks who are usually thinking, ‘I can’t do this, I haven’t seen someone like me out there’ — those are the people we try to attract and say come out there with us. We want everyone to feel at home on the sea.”

Saturday marks the first regatta for the Second City Sisters. The Chicago chapter — restarted in 2024 — has this year partnered with the Center on Halsted and the monthly Queer Sacred Space Salon at Lincoln Park Presbyterian Church, and it will fundraise with the AIDS Foundation of Chicago at this year’s Market Days.

“Usually, with our makeup and habits, we like to stay dry,” but Rainbow Races’ effort to diversify the sailing world is another cause worth supporting, Szymanski said.

Partnering with the local chapter of the Sisters of Perpetual Indulgence — a “legendary” queer organization — is “a big step” for Rainbow Races, which had not previously partnered with another LGBTQ+-serving organization, Thunkett said.

The appreciation is mutual, as this weekend’s regatta encourages queer people “to be their most authentic self,” participate in any activities they’re interested in “and do amazing things like sailing,” Thunkett said.