Heaton’s Emperia Wins Overall in Chicago
The 2026 Helly Hansen Sailing World Regatta in Chicago challenged teams as usual, with stiff early-season competition and conditions that kept the sailors guessing.
2027 SEASON — FIVE LEGS, ONE CHAMPIONSHIP
The Regatta Series That Is
American Sailboat Racing
One-design and handicap fleets race a five-stop national circuit each season, from the Gulf and East Coasts to the Great Lakes, culminating in a Caribbean Championship.
EVENT 04 OF 05 — 2027 SEASON
Chicago
June 11 – 13
Hosted by Chicago Yacht Club
Host Hotel
Located in the heart of downtown St. Petersburg, this intuitively designed AC Hotel reflects all the sparkle of St. Petersburg within a carefully crafted space defined by timeless appeal and true authenticity.
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Regatta Party Passes
Get your passes here for VMG access to the best post-race parties of the season. To: Purchase individual and discounted crew packs for fast and easy entry to the best post-race parties of the season. Cuisine, cocktails and good times guaranteed.
Mount Gay Rum
Cocktail Contest
Grab your mixers and whip up a thirst-quenching winner. Limited spots available.
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Regatta News: Chicago
The 2026 Helly Hansen Sailing World Regatta in Chicago challenged teams as usual, with stiff early-season competition and conditions that kept the sailors guessing.
Getting fast and having fun. That’s the Fleetwood way. The team’s leaders share their story of winning the Chicago regatta and the Caribbean Championship berth.
With a perfect scoreline, the hometown Melges 32 champs of PHRF bagged Chicago’s Caribbean Championship berth.
The forecast was iffy, but the breeze came on time for the Helly Hansen Sailing World Regatta distance race teams in Chicago. The one-design action continued on Lake Michigan.
At the Helly Hansen Sailing World Regatta Series in Chicago the seasoned regulars are leading the charge on the opening day.
We jump on board with Laura and Tone Martin in their new-to-them 65-foot ride for this summer’s Chicago YC Race to Mackinac.
