Becoming a 2-Sailboat Owner

When a one-boat owner gets the chance to be a two-boat owner, what's a sailor to do?

Sailboats on the water
The author keeps one boat up North and the other one down South for an “endless summer” of sailing. Herb McCormick

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If you were a baby boomer kid who grew up in the sailing-crazed town of Newport, Rhode Island, as I did, there was no way you didn’t have at least a passing familiarity with Pearson Yachts. They were everywhere on Narragansett Bay, built on Aquidneck Island in nearby Portsmouth. Even if you didn’t actually sail a Pearson, you probably knew somebody who built them.

I learned to race sailboats out of Newport Yacht Club on a pair of Pearsons—first a 26, then a 32—owned by the father of a high-school buddy. My first real taste of cruising under sail happened on another set of Pearsons—a 28-foot Triton to start and, later, a 32-foot Vanguard—both skippered by a fellow editor when I started working at Cruising World magazine.

And last spring, I became the proud possessor of my own good ol’ Pearson 365, a beamy, shallow-draft cruising boat designed by Bill Shaw and built in 1977.

OK, gulp, full disclosure: I now own a couple of Pearsons.

Sailboat at a dock
Last spring, I became the proud possessor of my own good ol’ Pearson 365, a beamy, shallow-draft cruising boat designed by Bill Shaw and built in 1977. Herb McCormick

In my defense, they are very different boats that reside in quite different locales. I purchased one Pearson—a 22-foot-6-inch full-keel, Carl Alberg-designed daysailer—a couple of years ago when I needed to find a boat quickly to secure my city mooring in Newport’s Brenton Cove. The fellow who owned it had retired to move south, and he had a sailing friend take charge of selling it, which the friend did for a ridiculously low price on Facebook Marketplace. I stumbled on it and got the best deal on any boat I’ve ever owned, and there have been a few.

My boat-buying luck held last spring while on a swing through Florida, where the son of my old mate Dan Spurr—the very same Triton/Vanguard chap referenced above—approached me on the dock at his marina on Longboat Key and said: “You’re just the man I wanted to see. I’m going to sell you my boat.”

Steve Spurr is an avid waterman who, these days, prefers Gulf of Mexico fishing jaunts on his center-console. He was eager to divest himself of one of his two vessels, a Pearson 365 called August West, so named for a character in a Grateful Dead song titled “Wharf Rat.” He was also utterly disinterested in the fact that I wasn’t in the market for a cruising boat. Like Marlon Brando in The Godfather, he made me an offer I couldn’t refuse, with the deal-sealer being the awesome boat slip on Longboat, adjacent to Sarasota Bay, where I could park it.

I always wanted a boat called Saunter, which I renamed Ensign, but never had one that fit such a stately moniker. But I like nothing better than summer sauntering through Newport Harbor on Ensign. It fits. With August West, I’ve decided to keep the name and do my own wharf-rat thing down the coast to the Keys this winter and, if I get ambitious, maybe even point her in the direction of Mexico or the Bahamas.

For now, the pair of Pearsons dovetail perfectly with what I want and need from a sailboat, at differing times and places. Though I didn’t realize it before it happened, it took two to accomplish the whole thing.  

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