Rainbow Regatta brings LGBTQ and ally sailors to Columbia Yacht Club
Mon. July 27, 2026 7:36 PM by GoPride.com News Staff
photo credit // michael oboza
From blessing to finish line, here's a look inside Columbia Yacht Club’s first Rainbow Regatta.
CHICAGO, ILL. -
By Michael Oboza, Special to GoPride.com
Founded in 1892, the historic Columbia Yacht Club on Lake Michigan, located at DuSable Harbor in downtown Chicago, recently hosted the Rainbow Regatta for the first time on Sunday, July 26, 2026.
A regatta is a series of boat or yacht races governed by formal maritime rules, often bringing together competitive sailors and local nautical communities. The Rainbow Regatta promotes diversity and equity for LGBTQ and ally sailors. The casual afternoon event was governed by U.S. Sailing Association rules and regulations and followed Performance Handicap Racing Fleet ratings.
The day's events began at 11:30 a.m. with a Blessing of the Fleet at the yacht club by The Second City Sisters Abbey of the Irreverent Bean, a local order of the Sisters of Perpetual Indulgence.
"This morning, we gather to bless the ships of the Rainbow Regatta," said Sister Auntie Gayme as she named the sailboats entered in the race: Rat Race, Radiance, Apostrophe, Endeavor, Mis En Place, Kookaburra, The Queens Revenge, Bloody Mary, Walrus, and Valkyrie.
"Through these ships, we follow an ancient and universal impulse to explore, to try, to be bold, to seek adventure! Our ships transport us to a freedom that doesn’t exist on solid ground," Sister Auntie Gayme said. "We thank each of these miracle-makers for giving us the power to walk on water."
"We ask our ships to protect us, as our one precious bit of control against the nearly infinite powers of the sky and sea," she added. "Let the mast of each ship stand tall and firm because that’s how we like them. Let our sails be even more full than the veil of a nun. May we trust our ships, our crews, and ourselves."
"May we reach that place with nothing but the horizon-line," she concluded. "Out there in open water, anxiety falls away, annoyances wash off, and even farts disappear into the wind. A good ship will give us that real-life fantasy, and a blessed ship will bring us home. Home to safety, home to victory, and home to a community of sailors who will stand next to you in any squall."
Following the blessing, participating vessels headed to the starting point near the Chicago Harbor Light. The Columbia Yacht Club race committee positioned itself over two miles from shore, checking in 10 sailboats before the official 1 p.m. start signal. While the committee often sails farther out for longer races with larger fleets, the competitors expressed clear gratitude as they checked in, with many shouting back, "Thank you, race committee!"
After the last boat crossed the finish line to wrap up the race around 4 p.m., an unusual situation arose when a sailboat radioed on VHF channel 78 to report it had run out of fuel. Adhering to the longtime maritime protocol of leaving no one behind, the race committee and captain located, spotted, and towed the vessel safely back to the harbor.
The day concluded with an evening celebration from 4 p.m. to 9 p.m. on the Columbia Yacht Club deck, featuring a dinner buffet, games, music, sportsmanship, and the presentation of race awards.
During the celebration, Columbia Yacht Club employee Tillian Joy reflected on their personal journey in the sport.
"As a queer sailor, I didn't know entirely how I'd fit into the community," Joy said. "I'm nonbinary. I use they/them pronouns. I didn't know how it would go down in the yacht club world. And it turns out, it turned out it's gone down just fine."
Rainbow Races Inc. is a 501(c)(3) nonprofit organization that connects LGBTQ and ally sailors while promoting equality through the sport. The group operates the only LGBTQ-sanctioned U.S. Sailing Association sailing school at Jackson Park Harbor, working to engage sailors of color and break down barriers in the marine industry.
"Rainbow Regatta Chicago is our signature event that launched the whole Rainbow Races Inc. enterprise," said Charles Szymanski, vice president of Rainbow Races Inc. and a longtime leader in the Chicago LGBTQ sailing community.
Founded in 1892, the historic Columbia Yacht Club on Lake Michigan, located at DuSable Harbor in downtown Chicago, recently hosted the Rainbow Regatta for the first time on Sunday, July 26, 2026.
A regatta is a series of boat or yacht races governed by formal maritime rules, often bringing together competitive sailors and local nautical communities. The Rainbow Regatta promotes diversity and equity for LGBTQ and ally sailors. The casual afternoon event was governed by U.S. Sailing Association rules and regulations and followed Performance Handicap Racing Fleet ratings.
The day's events began at 11:30 a.m. with a Blessing of the Fleet at the yacht club by The Second City Sisters Abbey of the Irreverent Bean, a local order of the Sisters of Perpetual Indulgence.
"This morning, we gather to bless the ships of the Rainbow Regatta," said Sister Auntie Gayme as she named the sailboats entered in the race: Rat Race, Radiance, Apostrophe, Endeavor, Mis En Place, Kookaburra, The Queens Revenge, Bloody Mary, Walrus, and Valkyrie.
"Through these ships, we follow an ancient and universal impulse to explore, to try, to be bold, to seek adventure! Our ships transport us to a freedom that doesn’t exist on solid ground," Sister Auntie Gayme said. "We thank each of these miracle-makers for giving us the power to walk on water."
"We ask our ships to protect us, as our one precious bit of control against the nearly infinite powers of the sky and sea," she added. "Let the mast of each ship stand tall and firm because that’s how we like them. Let our sails be even more full than the veil of a nun. May we trust our ships, our crews, and ourselves."
"May we reach that place with nothing but the horizon-line," she concluded. "Out there in open water, anxiety falls away, annoyances wash off, and even farts disappear into the wind. A good ship will give us that real-life fantasy, and a blessed ship will bring us home. Home to safety, home to victory, and home to a community of sailors who will stand next to you in any squall."
Following the blessing, participating vessels headed to the starting point near the Chicago Harbor Light. The Columbia Yacht Club race committee positioned itself over two miles from shore, checking in 10 sailboats before the official 1 p.m. start signal. While the committee often sails farther out for longer races with larger fleets, the competitors expressed clear gratitude as they checked in, with many shouting back, "Thank you, race committee!"
After the last boat crossed the finish line to wrap up the race around 4 p.m., an unusual situation arose when a sailboat radioed on VHF channel 78 to report it had run out of fuel. Adhering to the longtime maritime protocol of leaving no one behind, the race committee and captain located, spotted, and towed the vessel safely back to the harbor.
The day concluded with an evening celebration from 4 p.m. to 9 p.m. on the Columbia Yacht Club deck, featuring a dinner buffet, games, music, sportsmanship, and the presentation of race awards.
During the celebration, Columbia Yacht Club employee Tillian Joy reflected on their personal journey in the sport.
"As a queer sailor, I didn't know entirely how I'd fit into the community," Joy said. "I'm nonbinary. I use they/them pronouns. I didn't know how it would go down in the yacht club world. And it turns out, it turned out it's gone down just fine."
Rainbow Races Inc. is a 501(c)(3) nonprofit organization that connects LGBTQ and ally sailors while promoting equality through the sport. The group operates the only LGBTQ-sanctioned U.S. Sailing Association sailing school at Jackson Park Harbor, working to engage sailors of color and break down barriers in the marine industry.
"Rainbow Regatta Chicago is our signature event that launched the whole Rainbow Races Inc. enterprise," said Charles Szymanski, vice president of Rainbow Races Inc. and a longtime leader in the Chicago LGBTQ sailing community.