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.”
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.”