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Caribbean guru has seen everything

Cruising guide author Donald Street enjoys a cult following — meet him and you’ll see why

Street began writing his cruising guides in 1964.Here is Donald M. Street Jr.’s day as Caribbean guru at the Annapolis sailboat show:

8:05 a.m. — He is accosted by a total stranger who wants to shake his hand as he stands, unaccompanied, on the sidewalk, waiting to get a seat inside Chick and Ruth’s Delly. Once at a tiny table in this political feeding trough in Maryland’s capital city, he orders steak and eggs — an old submarine staple — in a loud crowd of patrons who seem oblivious to his celebrity.

10 a.m. — In the shoe department of Fawcett’s Boat Supplies, where a poster in the window announces the guru is inside, Street spreads copies of his five DVDs and three of his cruising guides on a table. Immediately, he sells and signs a DVD for a middle-aged man who confesses his admiration.

Noon — Street enters a large ballroom at the Marriott Hotel after arranging another display of his wares outside the entrance. He has recruited an accompanying journalist to operate his slide show, and he talks — with frequent references to his yawl, Iolaire — for an hour (in a nearly monotone voice that sounds like a rusty hinge) to a rapt, standing-room-only crowd of mostly middle-aged men and women. At the end, they press around his scrawny, scraggly person, as attentive as disciples.

1:30 p.m. — After selling and signing a ton of DVDs, books and charts, he grabs a beer before returning to Fawcett’s shoe department for more of the same. His wife, Trich, has been holding down the table in his absence. Street, who is 78, will end the day here hustling product with the energy the starving devote to eating.

Street's wife insisted that Iolaire's red hull be painted white for the yawl's 100th birthday.

A man of opinions

Don Street is perhaps the most successful entrepreneurial boat bum to have ever come ashore. His small nautical empire is based on a series of cruising guides he began writing in 1964 with the Yachtsman’s Guide to the Virgin Islands. (The cruising guides have spawned the videos and a line of charts for the Caribbean.) But on a deeper level, his notoriety is connected to one of his dominant qualities: Street has opinions.

He is “opinionated, but very informative,” says Gail Anderson, who edited his stories for Sail magazine and was a frequent guest on Iolaire in the 1970s and early 1980s. “I always came away from sailing with him having learned a number of things.”

Street, now 78, has been sailing Iolaire since 1957.“He certainly has an opinion, and he’s not afraid to let you know what that is,” says Jeff Curtain, a Rhode Island sailor who has cruised with Street since 1971. Often, he says, Street does not wait for his opinion to be solicited.

The crowds at Street’s appearances during the sailboat show testify to the merits of his opinions almost as much as to the skill with which he has been able to package and promote his ideas and his persona.

In the large community of would-be cruisers who realize they know nothing and are looking for a wise elder, Street’s floppy, broad-brimmed hat, his grizzled beard and his Bermuda shorts, supported at times by a length of rope, have become welcome symbols of experience.

Street was born into sailing knowledge. His great-grandfather raced sandbaggers on New Jersey’s Barnegat Bay. A grandfather raced Star boats on Long Island’s Great South Bay. And Street began sailing as a youth out of Manhasset Bay on Long Island’s northern shore.

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