Shoppers are turning to sun and sails: Rainbow Races, the nation’s only officially sanctioned LGBTQ+ sailing school, hosts its seventh annual regatta this Sunday at Columbia Yacht Club , a joyful fundraiser that opens the water to queer and traditionally disenfranchised sailors.

Essential Takeaways

  • What’s happening: Rainbow Races’ seventh annual regatta takes place at Columbia Yacht Club, with the fleet blessing at 11:30am and the race starting at 1pm.
  • Community focus: The organisation runs an LGBTQ+ sailing school offering U.S. Sailing keelboat certification and beginner sails, aiming to keep classes affordable and broaden access.
  • Festivities: Expect a blessing of the fleet by the Second City Sisters, an afterparty with a “Rainblow Regatta” model-boat race, DJ and games , lively and family-friendly.
  • Good to know: Navy Pier is the likeliest vantage point for spectators; bring binoculars since the course will probably be several miles offshore.
  • Why it matters: Funds raised help avoid class price hikes and seed scholarships, letting more queer and marginalised people try sailing.

A blessing of the fleet , and a splash of joyful theatre

The weekend opens with a theatrical, very visual blessing of the fleet by the Second City Sisters, Chicago’s local chapter of the Sisters of Perpetual Indulgence. Expect bright costumes, tongue-in-cheek ritual and a warm, inclusive energy that cues the day’s tone. The Sisters restarted in Chicago in 2024 and now partner with local LGBTQ+ groups. Sister Hooda Thunkett says the regatta “celebrates the way of the water” and brings lighthearted joy , a neat contrast to the serious seamanship that follows. For spectators, it’s a perfect photo moment and a reminder this is as much about culture and visibility as it is about competition.

Racing for a cause , how the regatta keeps classes affordable

Rainbow Races uses the regatta as its largest fundraiser, with ticketed afterparty plates and donations helping to underwrite the sailing school. The organisation offers U.S. Sailing keelboat certification and “first experience” sails, and leaders say the money raised will help keep prices low and fund scholarships. Charles Szymanski, the group’s vice president, explained they recently received a donated boat and want funds to launch and maintain it , a practical step that directly supports more training opportunities. If you care about widening access to outdoor sports, your ticket is doing more than buying a day out.

Where to watch, and what to bring

The race course is set on the day according to wind, which means the fleet could run several miles offshore. Navy Pier is likely the best public viewpoint, so plan to stake out a spot early if you want a good line of sight. Binoculars, sun protection and a small portable chair will make the experience comfier, and if you’ve got a camera with a decent zoom lens you’ll thank yourself. For those who prefer to be at the club, the Columbia Yacht Club hosts the afterparty , a chance to mingle with crews, volunteers and organisers.

Fun on deck and ashore , the Rainblow Regatta and afterparty

After the main race there’s a playful take on nautical sport: the Rainblow Regatta, where contestants race model sailboats by blowing on the sails. It’s charming, competitive and perfectly Instagrammable. Tickets for the afterparty are priced per plate and include the DJ and games , a fundraising dinner with a lively vibe. Even if you don’t buy a ticket, the spectacle and street-level festivities make for a weekend that feels open and celebratory.

Why this matters beyond the race

Rainbow Races explicitly aims to bring people to the water who might not see themselves in sailing , people who’ve assumed it isn’t for them. The organisation focuses on LGBTQ+ and traditionally disenfranchised communities, offering affordable classes, certification and outreach. Partnering with the Second City Sisters marks a new chapter in community collaboration, signalling that queer cultural institutions and sporting groups can amplify one another. It’s a quiet but meaningful step toward normalising queer presence in recreational sailing.

It's a small change that can make every sail feel more welcoming.

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