Deceased , Modern




1925 - 2003

Accomplishments and Honors

  • 2003 Awarded SAIL Magazine’s Industry Award for Leadership
  • 1970 Established the Annapolis Sailboat Show, the first and still one of the largest, in-the-water all sail shows
  • 1959 Founded the Annapolis Sailing School introduced more than 250,000 beginners to sailing
  • Commissioned Sparkman & Stephens to design the Rainbow for instructional and rental use
  • Set up Tidewater Plastics to Manufacture the Rainbow, built almost 500
  • Annapolis Sailing School established branches in Bermuda, Florida, South Carolina, California, Texas, Wisconsin and the U.S. Virgin Islands


The following was paraphrased from the Baltimore Sun:

Jerry Wood is the founder of the Annapolis Sailing School, which has been putting novice sailors at the helm since 1959. In doing so, he also has built a ready-made clientele for his later creation, the U.S. Sailboat Show, held annually in downtown Annapolis.

Not bad for a career that began at a beat-up old marina just across the creek in Eastport, Maryland, as a means of paying the grocery bill. “People had always had an interest in sailing,” Wood said in explaining his success, “but the way it had been presented until then was as an elite sport“. Then, he kept an 18-foot catamaran at a $5-a-month boat slip.

Having grown up in Westchester County, New York, he’d learned to sail at the Larchmont Yacht Club, just about the only kind of place a novice could learn to sail in those days, short of applying to the United States Naval Academy or learning from a friend. The Wood family’s toy manufacturing business  had closed the year before, and he was wondering what he should do with his life. He liked photography, and a public relations firm in the Midwest had offered a job, but one look at Chicago convinced him he’d be happier in Annapolis. Then opportunity knocked in the form of a man who approached with a question: Do you know where a guy can rent a sailboat around here? “Sure,” Wood answered. “I’ll rent you one for $20.”

When the same thing happened a few days later, he knew he was on to something. He placed newspaper ads in Baltimore and Washington, and the customers began rolling in. That might have been the limit of the venture, if not for a major shortcoming he noticed in his clientele. “A lot of them didn’t know how to sail,” Wood said. “There literally weren’t any sailing schools around. So that spring we started the boating school.”

From the beginning, he steered clear of the yacht club approach, remembering the sort of preliminaries at Larchmont that had bored him to tears and kept him off the water – stacks of paperwork about the differences between a brigantine and a barkentine and a ketch and a yawl, as well as the proper names and uses for everything from a mizzenmast to a running backstay. Wood geared his lessons to the practical side of sailing, the basics that would keep a novice afloat. “We demystified it,” he said.

Within two years, he’d designed his own teaching boat, the Rainbow, a 24-foot sloop. It was a forgiving craft that didn’t easily capsize, and its high-swinging boom didn’t hit so many beginners in the head. Five years later, he added another twist – lessons aboard a bigger boat that the students could live aboard for days at a time. Now, a customer could turn his lessons into a week-long vacation on the Chesapeake Bay.

By that time, Wood was peddling the Rainbow at boat shows, winter affairs in big arenas and convention halls in cities like Washington and Baltimore. But the events always bothered him.

“You’d come out at the end of the day with your eyes burning because of the overhead lights and the cigarette smoke,” he said – not exactly the salt-air invigoration of a day on the Bay.

Harvard University had just put a big bubble over its football stadium, and he thought he could put one temporarily over Annapolis City Dock and start an open-air show. He measured the dock and figured the cost – way too expensive. But the idea of an outdoor, on-the-water show stuck with him, and in the spring of 1970 he and business partner Peter J. Carroll decided to give it a try.

Wood’s school and his show put him in just the right position to capitalize on the sailing boom of the 1970s, and he figures the show draws about 40,000 visitors a year.

The peak years, when as many as 4,500 students a year would learn to sail in Annapolis, have passed. But business is still good enough to keep the school going locally and in two branch locations – St. Croix, Virgin Islands, and St. Petersburg, Florida. And anytime Wood wants to gauge his impact, he need only look out on the bay. Among the sails dotting the water on any nice afternoon, some are almost certainly trimmed and turned by his one-time students.


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