Regatta Series Brings The Big Fleets to Annapolis

It's a new season in Annapolis, and the Helly Hansen Sailing World Regatta Series is about to kick it off in a big way.
Regatta Series Annapolis
J/105 Class at the Helly Hansen Sailing World Regatta Series in Annapolis Walter Cooper

There’s a bizarre, but now seemingly sacred tradition in Annapolis these days where, come the spring equinox, boaters of all ilk gather round at the Maritime Museum and toss their token stinkers into the flames at the annual Sock Burning Festival. And not long after the embers die, boatyards are chucking boats into the Chesapeake at a harried pace. Annapolis YC’s Wednesday-night racing series kickoff comes next and then there’s the big season-opener: the Helly Hansen Sailing World Regatta Series. With more than 200 boats—224 to be exact on the eve of the regatta—and all area yacht club hands are on deck and this year’s edition is expected to be a spicy one. And we’re not talking Old Bay.

In taking a look at this year’s gathering, let’s first take a dive into the scratch sheet and the three new classes bringing some new blood to the regatta’s traditional lineup. The Albacore Dinghy fleet, which will be racing its North American Championship, has pulled in an impressive 19 boats, with nearly half of the doublehanded teams hailing from Canada, a hotbed of Albacore racing.

“There are 80 or so of them up there,” says Albacore stalwart Barney Harris, of Alexandria, Virginia, who has been racing the doublehanded dinghies since 1983 and has built most of the modern boats. “[In Toronto] they get somewhere between 30 and 40 boats on a regular night, and most of them very good.”

Harris has been building Albacores at his home since 2007 and is responsible for 17 new hulls, with No. 18 on the way, and he has raced every Albacore US National Championship since 1983. A diehard indeed, he’s also the reigning US National and North American champion and has an appreciation for the boat’s simplicity. “It’s not overpowered, but not heavy either [at 240 pounds],” he says, “simple but sophisticated enough to maintain my interest for a long time.”

While there are not that many Albacores local to Annapolis proper itself, the opposite is true for the regatta’s other hot class,which will be launching from Annapolis YC’s dry sail lot this weekend—the cruisy but competitive Harbor 20s. As a steadily growing fleet at AYC, this group has sat out the Helly Hansen Sailing World Regatta Series in years past as they prefer a more low-profile weekend experience for owners, but after a bit of cajoling from organizers, 19 of them are joining the fun for Saturday and Sunday only, on a racecourse set closer to shore where they prefer to play.

The Harbor 20, built by WD Schock in California, is best-suited for either two or three crew, and the class has strong pockets in the US, especially venues with protected harbors. With a deep and protected cockpit, a self-tacking jib and no spinnakers to fuss with, the Harbor 20 is as user-friendly as a one-design keelboat can be, and that’s the appeal for Annapolis’ Fleet 5 wrangler Bell Carty, who says, “We make sure that everything we are running is fun.”

Speaking of fun, there will be heaps of it for the sailors of the foiling Waszp one-design fleet, which is bringing out a big youth contingent with a couple of adults mixed in, including Annapolis YC’s own junior sailing coach who will be racing a few of his own charges for the first time. The regatta will also be his first time racing the Waszp that he bought a few months ago. The demands of high-school sailing coaching have kept him off the foil, so he has no lofty aspirations, but is happy to see juniors having fun.

“A lot of my kids are doing high-performance events around the Bay, so I figured I’d get into it too so I can see for myself what it’s about,” says Mitchell Powell. “As this will be my first one, we’ll see how it goes.”

What’s unique to the Annapolis stop of the Helly Hansen Sailing World Regatta Series is the strength of its established one-design classes, especially the J/105, J/80s and Viper 640s, that each have drawn in 25 teams per class. The J/70 fleet only beats that number by two. Each fleet has something on the line: for the Viper 640s, it’s the Atlantic Coast Championship title, for the J/70s it’s the coveted world championship qualification berths, and for the J/80s and J/105s, it’s simply local bragging rights, which locals know is a big deal in these ultra-competitive amateur fleets. Six of the J/80 teams are sailing for their own interclass bragging rights as participants in the American Sailing Association’s Performance Race Week + Regatta Experience, which includes two days of onboard coaching clinics before the racing starts.

2023 Regatta Series Annapolis
2023 Helly Hansen Sailing World Regatta Series Annapolis Walter Cooper

There will be plenty of other Regatta Series regulars as well, including the classic Alberg 30s and Cal 25s, the J/22s and J/24s, and Etchells classes, each of which have their returning champions back to defend. The J/30s, however, have lost their defending champion, Bruce Irvin, who was selected as the regatta’s overall winner in 2023 and earned a berth at the Caribbean Championship in the BVIs in October. Irvin, has traded in his J/30 for a custom 40-footer that he intends to race in Newport Bermuda Race someday.

As he and his crew are only now coming to grips with the boat, the Helly Hansen Sailing World Regatta’s two days of ORC racing will give Irvin and his young crew a chance to better learn the ropes and the choreography of their new-to-them yacht. Annapolis YC’s opening Wednesday night race in late April was their first official outing after a winter’s worth of boatwork.

“Mechanically it all went well,” Irvin says. “We’re just getting aware of all the lines, but to be honest, the boat is easier to sail than the J/30. Our goal this weekend is to hoist the ORC trophy, but first we’ll focus on getting it around the racecourse OK and getting some hours under our belts.”

The ORC fleet will race only Saturday and Sunday alongside the regatta’s other distance racers in the Beneteau First 24 division, and while all area clubs will be hosting fleets on the water, evening socials will be hosted by the Annapolis Yacht Club, with packed schedule of food, parties, games and a special, live Speaker Series evening with Ocean Race winning skipper and Rolex Yachtsman of the Year, Charlie Enright, on Thursday evening at the club.