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

Donald M. Street Jr. has become a fixture in the cruising community, admired as much for his practical knowledge as for his blunt, opinionated style. At the Annapolis sailboat show he demonstrates how his persona and work—cruising guides, charts and instructional videos—continue to draw attentive crowds of sailors and would-be cruisers.

Here is a typical day for Street at the show:

8:05 a.m. — While waiting outside Chick and Ruth’s Delly for a seat, Street is recognized and greeted warmly by a stranger. Inside, among the city’s political regulars, he orders steak and eggs. Even in a noisy room, people notice him and approach to say hello.

10 a.m. — At Fawcett’s Boat Supplies, a poster announces his presence. Street lays out his five DVDs and three cruising guides, and immediately sells and signs a DVD for an admiring customer.

Noon — In a Marriott ballroom he sets up his slide show, recruited a journalist to run the projector, and delivers an hour-long talk packed with references to his yawl, Iolaire. His voice may be low and rasping, but the audience—mainly middle-aged sailors—hangs on every word, surrounding him afterward like attentive disciples.

1:30 p.m. — After more sales and signings, Street grabs a beer and returns to Fawcett’s, where his wife, Trich, has been tending the table. At 78 he works tirelessly through the day, selling DVDs, books and charts with literal gusto.

A man of opinions

Street is perhaps the most successful entrepreneurial boat bum to have come ashore. His nautical enterprise began in 1964 with the Yachtsman’s Guide to the Virgin Islands and grew to include videos and a line of Caribbean charts. But beyond product lines, his reputation rests on something simpler: he has strong opinions—and he’s not shy about sharing them.

Gail Anderson, who edited Street’s pieces for Sail magazine and sailed with him frequently in the 1970s and early 1980s, describes him as “opinionated, but very informative.” Jeff Curtain, who has cruised with Street since 1971, says Street often offers his views whether asked or not. Those views, combined with a distinct look—floppy hat, grizzled beard, Bermuda shorts sometimes held up by rope—have become shorthand for experience among newcomers to cruising.

Street’s public appearances at boat shows reflect both the strength of his opinions and his skill at promoting them. For many inexperienced sailors seeking a knowledgeable mentor, his persona and straightforward guidance are exactly what they want.

Early life and priceless training

Street was born into a sailing family. His great-grandfather raced sandbaggers on Barnegat Bay; a grandfather raced Stars on Long Island’s Great South Bay. Street began sailing as a youth out of Manhasset Bay on Long Island.

At 13 he was already helming large yachts for races during World War II when fuel shortages meant boats had to be sailed to and from events. Those return trips, when skippers would hand the helm to young Street, were “training you could not buy today,” he says.

After high school he briefly attended college but enlisted in the Navy in 1949 to avoid the draft for the Korean War. He volunteered for submarines, later attended the University of Notre Dame and transferred to Catholic University in Washington, D.C. Street worked as a skipper and completed his degree at Columbia University in 1955.

He later turned down a job in marine insurance that required shaving his beard and instead flew to the Caribbean in 1956, working as a land surveyor before organizing yacht charters in 1958. In 1957 he bought Iolaire, a red, 46-foot wooden yawl built in 1906, and sailed her initially without an engine.

From charter captain to teacher

Street moved into the charter business early, reshaping it by taking paying guests who wanted to learn—apprentices rather than mere passengers. On Iolaire everyone worked: cooking, steering, maintaining the boat. Kenneth Breen, who sailed with Street in 1975 and later became dockmaster at the Boston Yacht Club, remembers Street as a patient teacher who explained tasks clearly and trained crew thoroughly.

During charters Street kept meticulous notes and carried a vast collection of charts—up to 120 from British, French and U.S. sources. He frequently used a lead line to take soundings in unfamiliar harbors, corrected chart errors he found, and reported them to charting authorities.

When corrections he sent to official agencies were ignored, Street approached private chartmakers. After one firm declined, Imray agreed to produce charts based on his inshore corrections. The Imray-Iolaire series replaced numerous government charts and provided 55 accurate, waterproof charts tailored for yachtsmen—an effort that significantly improved navigation safety for many cruising sailors.

Writing, editing and the love of teaching

Encouraged by others, including a chance remark from novelist John Steinbeck, Street began writing and worked with magazines like Sail. Editors found his manuscripts rich in detail but sometimes difficult to organize. Gail Anderson recalls manuscripts arriving on tissue paper to save airmail weight and notes that working with Street often meant shaping sprawling, story-filled copy into usable articles.

His writing and teaching style reflected an old-school belief in mastering many skills: celestial navigation, reefing, seamanship and a strict aversion to entering harbors at night. Anderson remembers Iolaire as red and unmistakable, “always fit, but never pretty,” and Street as an unrelenting storyteller who required good listening from those around him.

The video phase and ongoing legacy

In the 1980s Street produced a series of instructional videos that were later re-released on DVD. Titles include Street Wise volumes 1 and 2—practical tips for offshore preparation and sailing—Sailors’ Knots, which demonstrates knots and line-handling techniques, and Transatlantic with Street, a documentary of a 1985 ocean crossing. Antigua Race Week captures Iolaire racing around the buoys and shows Street directing crew in real conditions.

Street continues to sell his DVDs, books and charts; inquiries can be sent to [email protected]. He has also placed Iolaire on the market with the stipulation that the yacht go to the right buyer. If she doesn’t sell, Street plans more cruising, including a spring voyage from Ireland to Scotland to mark his 79th birthday.

This story originally appeared in the January 2009 issue.