Helly Hansen Annapolis Regatta 2026 Preview: J/Boats Fleets Shine

(Annapolis, MD)- The Helly Hansen Regatta 2026 returns to Annapolis, May 2-4, 2026 with more than 160 teams expected to race in boats ranging from 20 to 40 feet. Hosted by Annapolis Yacht Club, the annual spring regatta is considered the premiere local sailing event of the year on the Chesapeake Bay. The regatta also serves as the unofficial kickoff for the robust and thriving Annapolis summer sailing scene.

This year’s event will be heavily attended by J/Boats aficionados, with EIGHT one-design classes for J/22s, J/24s, J/70s, J/80s, J/88s, J/29s, J/30s, and J/105s! Plus, a few J/Boats are sailing in PHRF Spinnaker division.

J/22 Class
With seventeen entries, the J/22 fleet promises to be yet another shoot-out between the top crews from Annapolis and the upstate New York teams from the greater Rochester region- a hotbed of J/22 talent! The Annapolis local talent includes Jeff Todd’s HOT TODDY (recent winner of the Charleston Race Week J/22 class), Jake Doyle’s PINATA, Jeff Hayden’s POLAR EXPRESS, and Brad Julian’s YARD SAIL.

The leading New York mercenaries include Kevin Doyle’s MO’MONEY and Chris & Nick Doyle’s THE JUG 4 1. Then, two visiting teams from Rhode Island include Cory Sertl’s LUCY and Mike Gemperline’s DEFIANCE.

J/24 Class
The eight-boat J/22 fleet is comprised of Chesapeake Bay veterans of class wars over the years. Those teams include Bill Davenport’s ROO, Pat Fitzgerald’s RUSH HOUR, Pete Kassal’s SPACEMAN SPIFF, Sam Parson’s LUCKY 13, and two women-owned boats (Caroline Haddaway’s RADICAL J and Madeline Henry’s SISU).

J/29 Class
The five-boat J/29 fleet is comprised of three local teams and two out-of-towners. Defending home turf will be Elizabeth Principe’s THE DOGHOUSE, Alan Campbell’s NOTHING ARTIFICIAL, and Mike Baugh’s PERSEPHONE. The “foreigners” include Collen Wellington’s RED DOG from Sandusky Sailing Club and Jon Burnham’s DEFIANT from Riverton YC.

J/30 Class
The five-boat J/30 class will be the host Eastport YC’s internecine battle for club bragging rights! Those teams include Dan Watson’s AVITA, Jim McGinnis’s BLITZ, Jim Burdick’s ONE LOVE, and two boats from Valhalla Sailing Club.

J/70 Class
With thirty-two boats, the J/70 fleet will be enjoying a “de facto” East Coast Championship, as most of the top teams from the East Coast are participating. Those teams include Mark Hillman’s “6”, Paul Green’s PROGRESS, Kelly Hansen’s 7TH HEAVEN, Jim Gary’s AYACUCHO, local hero Terry Hutchinson & Jen Norwood’s ELLIE, Tod Sackett’s FM, Mike & Trish Kirkman’s HOT TICKET, Brian Keane’s SAVASANA, Sandy Askew’s TANGERINE, Henry Filter’s WILD CHILD, and Alec Cutler’s Bermuda team on HEDGEHOG.

J/80 East Coast Championship
The J/80 class has turned out in full force for their 2026 J/80 North American Championship. Twenty-three teams will be vying for the top of the leaderboard and the honor to be crowned the 2026 N.A. Champion. Some of those teams should include Mike Beasley’s BLACK SHEEP (fresh off a Charleston Race Week win), Bengt & Marie Johansson’s BLAZE, Bert Carp’s ELEVEN, Tom Kopp’s KOPP-OUT, Ramzi Bannura’s STACKED DECK, JR Maxwell’s SCAMP, and the Russell Family on WILD HORSES.

J/88 Class
Another class that is sailing a “de facto” East Coast Championship are the J/88s. A strong fleet of nine boats from across the northeastern seaboard and some “spoilers” from Chicago will be ready to race on the choppy waters of Chesapeake Bay. The leading teams include past North American and Great Lakes Champions (including Chicago-Mackinac Champions). Those crews include Justin Scagnelli’s ALBONDIGAS, Iris Vogel’s DEVIATION, Andy Graff’s EXILE, Bill Purdy’s WHIRLWIND, Chris Chadwick’s CHURCH KEY, and Jack McGuire’s MI-2.

J/105 Class
The “creme-de-la-creme” are making their presence felt for the twenty-three J/105 fleet. Several veterans are participating, all having won or podiumed in the J/105 fleet in previous major events. Those teams include Doug Stryker’s MAYHEM, Don Santa’s SANTAS REIGH DEAR, Ben DuPont’s WAR BRIDE, Cedric Lewis’s MIRAGE, Ray Wulff’s PATRIOT (the 2025 class winner), Carl Gitchell’s TENACIOUS, Kristen & Brian Robinson’s VELVET HAMMER, Peter Bowe’s GOOD TRADE, and Bill Zartler’s DEJA VOODOO.

PHRF Spinnaker Division
The most interesting entrant in this fleet will be Gary Jobson sailing J/7 USA 1 amongst the 30-40 footers! Watch out, local hero Jobson could surprise a lot of teams! He will be up against Keith Cole’s J/124 LUCKY EIGHTS and Jim Sagerholm’s J/35 AUNT JEAN (another famous local boat and perennial winner)!

For more Helly Hansen Annapolis Regatta sailing information
https://www.yachtscoring.com/emenu/50501