Home Features In Depth Caribbean guru has seen everything

Caribbean guru has seen everything


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 This e-mail address is being protected from spambots. You need JavaScript enabled to view it . 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.

fbtwit yt

Great Gear,