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

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.