Don Street turns 84 in July, and if his golf game was as good as his sailing game, he’d probably be shooting his age.

“The 18-foot pulling boat and Gypsy are both in the water,” Street wrote me last spring. “The Dragon racing starts this weekend!!!”

To this day, Street remains as active in the sailing world as he has been most of his life. He still races weekly on his 76-year-old Gypsy, aboard which he is “still out there giving the youngsters a hard time.” During the winter, he also serves as a “rock pilot” and tactician on larger race boats in the Caribbean.

Street spent most of the 1950s and 1960s cruising the Caribbean —before the guidebooks, before the mooring balls, before the amenities. In fact, he wrote the books and drew the charts, and it’s in large part thanks to his efforts that the Caribbean is so accessible today. His Cruising Guide to the Lesser Antilles, published in 1966, literally opened the Eastern Caribbean to cruising yachtsmen and made chartering possible. What makes him all the more legendary is that he did most of this aboard a his iconic antique engineless wooden yawl, Iolaire.

The house he now occupies in Glandore, Ireland, is just a block off the waterfront. He has converted the sunroom out back into an office of sorts, with the original tiller from Iolaire, his old yawl, hanging on the back wall next to photos of his sons sailing J Class yachts and other big boats in various parts of the world. Copies of seemingly every issue of every sailing magazine ever published lay scattered around the floor when I visited him there.

It’s his wife’s house, actually, and to Street this is an important distinction. He has seen himself as a “wandering sailor” ever since he was displaced from Grenada after the 1983 invasion. “The People’s Revolutionary Army seized our two houses and five acres of land,” Street told me, “and we were never allowed back.” Hence his “guest room” in Ireland.

Don Street Was Once Young

“You might just say Street is a tough old goat,” he told me, speaking in the third person. “When he gets knocked down, he just gets up and gets on with life!”

At the age of 13, in Manhasset Bay on Long Island, where he grew up, his left hand was crushed between the bow of a boat and a dock—so badly that it was almost amputated before a young surgeon said he thought he could save it. Street was pushed hard by his mother and by his desire to keep sailing, and with considerable pain and physical therapy, managed to get the hand in working order again, though it still gives him trouble when the weather gets cold and gray.

Street was hardest hit when his first wife, Marilyn, was murdered by burglars in St. Georges, Grenada, during the 1950s, a fact he’s kept pretty private all these years and doesn’t like to talk about.

“Needless to say that knocked me for six,” Street told me when I hesitantly asked him about it.

“Life must go on,” he continued. “I had a 20-month-old daughter, Dory, to raise. My family rallied around us. My sister took Dory in the winter while I chartered, and Dory came down in the summers. To keep from thinking of the past, I worked like mad on various projects like finishing the Cruising Guide to the Lesser Antilles, which I dedicated to Marilyn.”

Could this explain why Street has been so prolific throughout his 70 years on the water? Might he be running from those sad memories, keeping them out by flooding his mind with work? Always moving forward, never back.

“As my grandmother always said, ‘God writes straight with crooked lines.’ While I was anchored in Carriacou, an engineer friend came out to find out how far to build his dock for the fueling station. He was accompanied by a little Irish gal named Trich, who I talked into going on a short sail. Then it was a longer sail, then another. Trich became my wife. She raised Dory and presented me with three sons. Forty-six years later we are still married.”

Down to the Sea in Ships

Street cut his teeth in professional sailing in 1955 at age 24, after a stint in the Navy, where he’d volunteered on submarines. “I got hired as a paid hand for the late Huey Long on Ondine, which was a 53-foot Abeking & Rasmussen yawl,” he told me. “A month after I arrived they fired the skipper, and I ended up in charge!”

Street campaigned Ondine in Scandinavia that summer, competing in the first-ever Gotland Runt, which today is the largest offshore race in the Baltic. While preparing for the Fastnet Race in the U.K., Street got fed up with skippering someone else’s boat and made an impromptu decision. “The owner was squawking about a water bill,” he explained. “I told Huey exactly where the hell to go with his boat and his mast and everything else and stormed off the boat!”

He wound up on another boat for the Fastnet, Lutine, which happened to belong to Sandy Harworth, a leading marine underwriter. Later his connection with Harworth helped him land a job at Frank B. Hall & Partners, a big marine insurance broker on John Street, in “the canyons of Wall Street.” Though he ultimately did represent insurance brokers in the West Indies, this first step into the business proved to be a false start.

“I never showed up!” Street exclaims. “Two days before I was supposed to start I flew the coop!”

Instead, Street bought a plane ticket to St. Thomas. His ride south on the “vomit comet,” as he calls it, was the start of a career that would last for decades.

The Making of a Legend

But it didn’t happen immediately. In fact, from the stories he tells, it’s a wonder he ever accomplished anything. Street bounced around the Virgin Islands doing various jobs to stay busy, enjoying himself in a place where nobody cared if he had a beard. His first “real” work experience came as a surveyor.

“I didn’t know a damn thing about it,” he admits. “I bought a book on Friday and by Wednesday had convinced them to hire me. I figured it was just like navigation, except you knew exactly how far you went!”

At this point, Street’s Caribbean odyssey divided into two branches. The first was his long-term love affair with Iolaire, which he bought in St. Thomas in 1957 and set to work in the charter trade. Two years later she was driven ashore and wrecked when an anchor shackle parted, but Street, in typical style, salvaged and repaired her on the fly, and had her out on charter again just 13 weeks later.

The second was what became a systematic exploration of the Caribbean, during which he wrote the guidebooks and drew the charts that eventually helped turn it into the place we know today. At the time it was impossible to get accurate charts of the Caribbean so Street got hold of an 1867 edition of Norie & Wilson’s Sailing Directions to the West Indies and started taking notes. These eventually became his own sailing directions.

“As I explored, I realized that not only were the charts based on ancient surveys and weren’t that accurate, but there were areas that had changed,” Street told me. “They were very poorly broken up. The U.S. chart of the Virgin Islands stopped in the middle of Virgin Gorda! Anegada was terra incognita!”

In 1979, Tom Wilson of Imray Charts agreed that Street’s idea of charting the Caribbean would be “a nice little project.” Street claims his wife thought income from what became known as Imray-Iolaire charts would at least provide whiskey to drink at boat shows. “There’s no way we’d be able to drink all the whiskey it’s provided!” he says now with a chuckle. To this day Garmin, Navionics, Jefferson and France-based Map Media, all continue to use information from Street’s Imray-Iolaire charts.

Present at the Creation

Then there’s the story of Street’s involvement in the bareboat charter trade. “I can honestly say that I was the one that kick-started the bareboat industry,” he says with a mix of pride and disgust.

In the 1960s and 1970s, the charter trade in the Caribbean was essentially a collection of one-off yachts, with or without captains and crew. It was impossible to get spare parts, and everything was always breaking down. To make a long story short, Street essentially talked through the design of a 41-foot purpose-built charter yacht with the principals of what would become Caribbean Sailing Yachts Corporation, CSY, sketching particulars on a napkin just prior to the New York Boat Show.

“We fitted it all together and had an accommodation plan,” Street told me. “So we open up the booth. Jack Van Ost is there saying, ‘You invest money, you’ll get a boat, and you can make money.’ I’m at the other end of the booth saying ‘Forget about what Jack says! You can invest this money, put this deposit down, pay for the boat. You’re not going to make any money, but you’ll have a boat down there you can use for six weeks!’”

“In one show we took deposits on 37 boats!” Street says with a wry smile.

The charter industry hasn’t looked back since.

Timeless Advice

More than any other sailing writer alive or dead, Don Street has shaped my views on sailing and seamanship. I first discovered him on the far end of a bookshelf in my Mom and Dad’s basement: Street’s The Ocean Sailing Yacht, and The Ocean Sailing Yacht, Volume II. Even 40 years after they were published, I’ve come to consider them the bibles of ocean cruising.

Truths reveal themselves—both about sailing and about Street himself—throughout OSY I and II once the fog of the myriad technical details lifts. It’s these unearthed truths that keep the books, and the man, relevant today. Street speaks in specifics for sure—indeed, perhaps the most valuable part of the books are the appendices, listing everything from metric-standard conversion tables to breaking strengths on metals commonly found on boats—but it’s his overarching philosophies that make the books timeless.

In Street’s view, there is no wrong way to sail a boat. You’ve just got to keep experimenting. Sheeting headsails to the end of mainsail booms, adjusting leads here and there, balancing out the boat by playing with sail area fore and aft (one of the main reasons he loves the yawl rig so much). In his mind, if it doesn’t work, try something else. That’s the point.

“When I look back at my sailing experience over the last 70 years, 57 of it offshore, I feel I have forgotten more about seamanship than most of the magazine editors are going to ever learn,” Street tells me. He’s passionate about his place in the canon of sailing, and he defends it to this day.

Granted, Street is not the same Street he was in his heyday, but he’s 80 percent of it. Iolaire, the yacht that made him famous, has been sold to a loving new owner, and in 2010 Street enjoyed one last sail on her. “With my 80th birthday approaching, it was time to quit sailing Iolaire while I was still fit enough to run around on deck and do everything,” he told me.

Street had owned the boat for 53 years and four months and called the sale of her “the end of an era.” He delivered Iolaire to the U.K. from his home in Glandore, with the new owner onboard as skipper and Street as sailing master. “People ask me if I would like to sail on her again,” he says. “The answer is NO! That last sail was so near perfect that any other sail would be downhill.”

Meanwhile, Don Street is as passionate as ever about the truth as he espouses it. Lately he’s been evangelizing about going green—installing hydro-generators and wind power on ocean voyaging yachts to cut down on diesel consumption—and proper manual bilge pumps, a relic from his days in the marine insurance business. Street hates reading stories about yachts being abandoned due to hull breaches because the crew didn’t have the proper equipment to save the boat.

Unfortunately, as his voice gets older and squeakier, it seems it is drifting further and further from the ears of modern sailors. But I’m still listening, and I have a feeling I’m not the only one.

A Complete Guide to Don Street’s Books, Charts and DVDs

Ask Don Street how he got into writing and you’ll soon be lost in a convoluted anecdote about the pioneer years of Caribbean chartering. The short version is that during one charter he happened to have dinner with John Steinbeck in Caneel Bay on St. John. As Don tells it, Steinbeck turned to him and said, “Kid, you tell a good story. Why don’t you try writing?” Don protested that he couldn’t spell or punctuate, to which Steinbeck replied, “What the hell do you think editors are for?”

Since that fateful conversation, Don has published about 300 magazine articles and an impressive list of books, including Ocean Sailing Yacht Volume 1 (pictured) and A Cruising Guide to the Lesser Antilles (1965).

Books

– The Ocean Sailing Yacht (1973)

– The Ocean Sailing Yacht Vol II (1979)

– Seawise: Helpful hints, warnings and common sense for the yachtsman (1979, 1980, 2004)

– Street’s Transatlantic Crossing Guide (1989)

Cruising Guides

– Street’s Guide to The Cape Verde Islands

– A Cruising Guide to the Lesser Antilles (1965, 2001)

– Street’s Cruising Guide to the Eastern Caribbean: Puerto Rice, the Spanish, U.S. and British Virgin Islands (1964, originally)

– Street’s Cruising Guide to the Eastern Caribbean: Martinique to Trinidad

– Street’s Cruising Guide to the Eastern Caribbean: Anguilla to Dominica

– Street’s Cruising Guide to the Eastern Caribbean: Venezuela and the ABC Islands

Imray-Iolaire charts imray.com

DVDS

Transatlantic with Street

Don Street may be the only skipper to achieve 9 trans atlantics purely under sail. In this DVD, viewers cross the Atlantic with him. “Before the ARC and GPS, it was sextant, DR and basic RDF. A transatlantic passage was a real adventure. There were no Guides to any of the islands, it was truly a voyage into the unknown”

Sailor’s Knots: Line Handling and throwing

Don teaches his 8 essential knots plus the rolling hitch, fisherman’s bend and tow-boat hitch in an effort to equip any crewmember to competently add to their ship by properly tying and throwing lines

StreetWise 1 and 2

Back in the 90s Don’s Streetwise tips were so well liked that during the winter months some yacht clubs would have “Street look-alike contests. In Streetwise 1, Street covers single line docking, chafing gear, snubber lines and getting off once you’re aground, plus more. In Streetwise 2, he covers heavy weather, jibe perfection, navigation, cleating line, tying sheets, Venezuela and Ireland.

Don Street Antigua Race Week

A one-hour documentary that takes you on board Iolaire during Antigua Sailing Week ’85, her last entry into the event.

Andy Schell is a sailor and journalist who contributes frequently to SAIL. Check out his blog and podcasts at 59-north.com