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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

Here is Donald M. Street Jr.’s day as Caribbean guru at the Annapolis sailboat show:

Street began writing his cruising guides in 1964.

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.”

“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.

Street, now 78, has been sailing Iolaire since 1957.

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.

Priceless training

When he was only 13, he got his start sailing big boats from his local yacht club. It was during World War II, and fuel was in short supply, so when yachtsmen would enter a race across Long Island Sound, the boats had to be sailed to and from the events. On the return trips, the skipper would hand the helm to young Street. It was “training you could not buy today,” he says.

He graduated from high school in 1949 and entered college. But, concerned that he would be drafted for the Korean War where he envisioned himself in a “foxhole in the Pusan perimeter,” he enlisted in the Navy. Despite his sailing background, he got orders for diesel engineman’s school, so he volunteered for submarines.

Street saw no action during the war, was discharged and spent time attending the University of Notre Dame before transferring to Catholic University in Washington, D.C. He worked as skipper of a 53-foot yacht on Long Island Sound and commuted to Columbia University for his last six credits, graduating in 1955 with a degree in history.

After working on yachts, Street got a job in a firm that sold insurance to the shipping industry. There was a condition, he says. He had to remove his beard. He never reported to work. Instead, in December 1956, he took a friend’s advice, flew to the Caribbean and found work as a land surveyor, a job he held for two years.

In 1958, Street says, he began organizing yacht charters in the Caribbean, having “decided that was better than climbing up and down hills carrying a [surveyor ’s] transit.”

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He had purchased Iolaire, a red, 46-foot wooden yawl, in 1957 for $3,000 down and $1,000 a year for four years. Street says he sailed Iolaire, built in 1906, for a year and a half with no engine until fate intervened.

Along the way, Street began selling yacht insurance. Back during his college days in Washington, he had signed on as crew on a yacht owned by the Lloyds insurance people. Through the contacts he made then, and his understanding of yacht construction, he says he found entrée to the insurance business.

‘A bit of a con man’

His education in yacht design was abetted by the fact that, as he says, “I am a bit of a con man.” In college, Street says, “I conned my way into a … pass to the Library of Congress.” He held on to the pass and used it to educate himself in naval architecture. “I’m a frustrated yacht designer,” he says.

“I learned that if you don’t know the answer to a question, someone else does,” Street says. “Seek him out, either personally or from his writing.”

His knowledge came in handy when Iolaire’s anchor shackle broke and the yacht washed ashore, a wreck. He says he bought the boat back from the insurance company for $100, paid some shipwrights, recruited a score of friends, replaced frames and planking, installed an engine and “was out on charter 13 weeks, three days after purchasing [the] wreck.”

Eventually, Street ditched the new engine, burnishing his image in the cruising and chartering community.

He had entered the charter industry in its infancy. In its early adolescence in the late 1960s, he changed the terms of the business. Now, he accepted paying guests who were sailing apprentices, folks who wanted to learn about sailing.

The difference, he says, was that “in chartering, I went where the charterers wanted to go. Paying guest sailing apprentices, they went where I wanted to go, investigating for charts and guides. If they complained about a leak over their bunk, I would tell the sailing apprentice to find the mate, and he would show them how to repair the leak.”

Kenneth Breen, now the dockmaster at the Boston Yacht Club in Marblehead, Mass., was, for a time, a paying crewmember on Iolaire in 1975. “Everybody on the boat was required to do everything that was involved in running the boat,” Breen recalls. “You did the cooking, did the dishes, [the] steering.”

Hunting chart errors

Breen graduated to non-paying crewman, making two trans-Atlantic voyages with Street. “He’s a very good teacher and a very good instructor,” Breen says. “He always took the time to explain things to people and guide them through whatever the task was or whatever they were trying to learn.”

During these charters, Street took notes that became the source for his cruising guides. He had aboard Iolaire 120 charts from the British Admiralty, the French and the United States. In any new harbor, he would dinghy about with a lead line, taking soundings. When he discovered an error, he would record it and inform the responsible charting authority, he says.

So when Street began adding charts to his cruising guides to gain a competitive edge, he had more than 20 years of charts marked up with errors. “The only places I haven’t been, it’s noted [that] I’m using secondhand information,” he says.

“As I continued to write guides, I discovered all the corrections I had been sending in [to the charting authorities] had been ignored,” Street claims. And so, while attending the London boat show in 1979, Street approached a British company that sold privately printed charts and suggested they use his information.

“I was turned down, flat,” Street says. Ever the hustler, he went around the corner to Imray, a rival chart company, whose owners said: “Let’s give it a go. Nice little project. [It] will produce enough money to buy whiskey at the boat show,” Street says.

“Little did they realize how big the project would be,” Street says. “I did not re-chart the Caribbean [but] corrected the inshore portions [of existing charts] where I had discovered errors, then broke them up into sections that were suitable for a yachtsman.” The final result, the Imray-Iolaire charts, contained “55 accurate, waterproof charts [that] replace 120 government charts of dubious accuracy,” Street says.

Meanwhile, Street recalls, he had been encouraged to try writing by a novelist of renown. Street says John Steinbeck told him: “Kid, you tell a good story. Why don’t you try writing?”

“To which I replied: ‘I can’t spell or punctuate,’ ” Street says. “To which Steinbeck said: ‘What the hell do you think editors and secretaries are for?’ ”

A teacher at heart

One of the magazines to take on Street was Sail. Retired publisher Don Macaulay notes that “Street had been in the Caribbean for decades and had strong feelings about the nascent bareboat chartering business, government nautical charts … anchoring and anchors … the worthlessness of an engine on a sailboat, the near-perfect rig, lee shores, hard tenders versus inflatables, and ice in one’s whiskey. He also had … a love of teaching.”

Macaulay recalls vividly his first meeting with Street at a boating industry party. “I knew he had come [from a] Long Island family with a banker for a father,” Macaulay says. “I was shocked. Here was this thin-as-a-rail guy, duct-taped boat shoes, burned nose, untrimmed beard, squeaky voice, matted hair, wrinkled … necktie (wide — out of style) and a blazer that clearly had the bottom spot in his duffel. He was gorging like a starving man at the buffet. Well, I said to myself, ‘This guy has re-created his persona as if done in a stage dressing room to fit the part.’ ”

Mining the nuggets

Anderson was the person at Sail assigned to edit Street. The job had its perils and its benefits.

“As an editor, my biggest challenge was to get him organized,” Anderson remembers. “He would go off on tangents. There was a lot of knowledge there, but we needed to smooth it out a bit.

“He worked from an old Olympia typewriter,” the editor continues. “I would get these manuscripts mailed on tissue paper [to save weight for air mail], which was cut and stuck together with Scotch Tape. And it was difficult to contact him those days. No e-mail or cell phone.”

The payback for the editing was sailing on Iolaire. Invitations were accompanied by shopping lists. Street asked Anderson to bring a gallon of paint or a few hundred feet of line aboard her flight.

“I think everybody in the Caribbean knew Iolaire because she was red,” says Anderson. “The boat and the guy, I guess, were a perfect match because they were both characters. Iolaire, an ancient yawl, heavily sailed. Donald did not believe in an engine. So here we are with a venerable yawl built in the British Isles many decades ago, without an engine, being sailed the length of the Caribbean in waters that are often quite dangerous.”

Iolaire was “always fit, but she was never pretty,” Anderson says.

“One of the things that I think makes him one of a kind is how knowledgeable he was about everything,” says Anderson. “He was of the old-school [belief] that you needed to know everything; celestial navigation, every reef. You never, never, never entered harbors at night.”

Anderson remembers a time when Iolaire was moored in a crowded harbor. With the jib and the mizzen sail raised, Street sailed off the mooring and out of the harbor, she says. “He could sail that boat backward. It was extraordinary.”

The editor found her writer to be a person with an endless fount of stories. “You had to be a good listener if you were with him because he never stopped talking,” she says. Street produced “a steady stream of words from when he got up in the morning. I enjoyed it.”

The video phase

In the 1980s, Street’s words — and his image — were captured on a series of videos. Recently, five of these films have been re-released on DVD. These are among the wares Street was selling at the Annapolis show.

Two of the DVDs — Street Wise, volumes 1 and 2 — are collections of tips for sailors preparing to go offshore and sailing offshore. Even an experienced bluewater boater probably will find some valuable insights.

In Sailors’ Knots, Street shows standard knots and some useful variations and demonstrates techniques of line handling and throwing. Again, almost any sailor will find a nugget or two in a series of easy-to-follow demonstrations.

Transatlantic with Street is a film documentary of a 1985 trans-Atlantic voyage on Iolaire with a crew of paying customers. The DVD contains occasional tips for the ocean sailor who is willing to endure the 1970s musical soundtrack and some hokey staged segments.

Antigua Race Week is another 1985 film capturing Iolaire’s final around-the-buoys race. It shows the yacht’s owner unvarnished, giving direction to the men and women aboard. It’s the sort of film sailors can appreciate when, on a dreary winter night, they want to dream nautical dreams.

The DVDs, books and charts can be purchased by e-mailing Street at In addition to his other products, Street has put Iolaire on the market, but he says he will sell only to the right person. If that person doesn’t arrive before spring 2009, Street has the next cruise planned — from Ireland, where he and Trich live — to Scotland, where he would celebrate his 79th birthday, and return.

This story originally appeared in the January 2009 issue.