Jerry Wood: Sailor and Sailing Entrepreneur

A Tribute to Jerry Wood, Founder of Annapolis Sailing School and Annapolis Boat Shows and National Sailing Hall of Fame Inductee 2024

It wasn’t that bad. My fellow Annapolis Sailing School instructors had warned me that Jerry Wood’s homemade ice cream, which he brought down to the docks once every summer, would be disgusting. I thought it was pretty good.

Looking back on it now, what a nice guy Jerry was! To bring homemade ice cream to a few dozen (ungrateful) teenage and 20-something sailing instructor employees on a muggy July day. To care enough to spend some time with us, get to know us, if even for a day. Here he was close to retirement age as the founder (1959) of what was considered the oldest and largest sailing school in America with schools in various locations (at the time) in Annapolis, Florida, and the US Virgin Islands; the founder of the Annapolis Sailboat Show (1970); and owner of a yacht he actively sailed along the East Coast, yet he still found time to make that ice cream, shake our hands, and talk about sailing.

jerry wood annapolis sailing school
Jerry Wood shared his sailing passion with thousands as the founder of Annapolis Saling School and Annapolis Sailboat Show. Photo by Jeff Holland

In June, when I learned about the late Franklin “Jerry” Wood’s induction to the National Sailing Hall of Fame (NSHOF), my first thought was how thrilled he would have been by the honor. He’d earned it. I thought about the beautiful timing, as the Annapolis Sailing School celebrates its 65th anniversary this summer. Remembering Jerry, or Mr. Wood as we called him, so many fond memories bubbled up to the surface.

In the late 1980s into the early 1990s, Annapolis Sailing School kept its substantial fleet of three dozen Sparkman & Stephens-designed Rainbow 24s on the docks down Bembe Beach Road at the mouth of Back Creek. We proudly described to our students how Mr. Wood had helped to design the boats for ease of student use and how they were so sturdy that the US Naval Academy had bought a fleet of them to train Midshipmen (later replaced by Colgate 26s).

Down Back Creek, behind the Woods’ house in a protected cove, the school kept its larger boats: a fleet of cruising boats ranging from 26 to 40 feet, including one of those O’Day 37s with the aft cabin (suited for the teacher-captain) and center cockpit, a fairly bullet-proof sloop, as remain the Rainbows.

Rainbows Annapolis Sailing School
Annapolis Sailing School's Rainbows, newly refurbished, on the docks today on Back Creek off the Chesapeake Bay in Annapolis, Maryland. Photo courtesy Annapolis Sailing School

Every once in a while, on a slow weekend, a few instructors would get sent back to “Woods’ Cove” to scrub decks. Word on the docks was to mind yourself back there, as Jerry’s wife Kathy was often home with her eye on the cove and sailboats. Kathy was known to shout out a window to a deck-swabber who was lollygagging on the clock.

I remember interviewing Jerry for a magazine article for the now-defunct Inside Annapolis Magazine in the mid-90s. He loved to recount how everyone thought he was nuts for starting a boat show. “No one will come,” they’d told him. Reportedly, 15,000 show attendees showed up at the inaugural event. Grinning widely, Jerry claimed that the restaurants ran out of food.

Last spring, the Annapolis Sailing School’s current owner, Rick Nelson, reached out to me about gathering instructor stories for the school’s 65th anniversary. He wondered if anyone had a “life-changing experience” at the school. That would be me.

If it weren’t for my years teaching sailing there and the friends I made, namely SpinSheet co-founder Dave Gendell (who was a college kid back then), I wouldn’t be working at SpinSheet. Jerry Wood and his sailing school—which started as one guy, one boat, and a great idea—changed my life and the lives of countless sailors.

This month, I celebrate 18 years working at SpinSheet in what’s truly been a dream job, combining my passions for sailing and writing. I think Jerry would be proud. I’m going to get some ice cream in his honor.

~Molly Winans, SpinSheet Editor

Learn more about the NSHOF’s 2024 class of inductees at