The American sailing author, pilot of the Caribbean Don Street died aged 93 in May 2024 at his home in Glandore, Ireland. Dan Houston looks back on his life and describes how it was sailing with him aboard his engineless boats

Don Street 26th July 1930 – 1st May 2024  –  By Dan Houston

 

Iolaire, the yacht Don made famous through the Imray charts

The first time I tried to go sailing with Don Street was back in the late 1990s. He’d invited me to sail with him on his famous engineless old cutter after we’d met and had a beer at the London boat show. I’d told him how, about 15 years earlier, his Caribbean pilot guide had saved us from hitting a reef off the north coast of Antigua. Our chart – likely from a survey made more than 100 years before, had not shown it; one of the local guys aboard mentioned it and skipper Dennis Ord had checked the “Street Map” as he called Don’s guide. “HARD-t’-STARBOARD!!” was his reaction. On the square-rigged topsail schooner we’d jumped to the sheets and braces, and slewed off to the west, thanking our lucky stars – as we’d been making about 12 knots. And thanking Don’s great knowledge.

But I wasn’t allowed to go on this passage. The editor felt that he was saving me from being damaged by the effect of Don’s voice. (Yeah really!) I always thought that Don was called Squeaky because of how he sounded on the VHF, but there was more to it than that… At a show he could talk like the Gulf Stream; you could find yourself getting carried away – quite a long way – on his mesmeric creaky drawl.

Of course I argued to go, and I always regret missing out on that sail. It was some years later, when I had returned to the Caribbean, I came across him sitting upstairs at the Yacht Club in Falmouth, Antigua. He was nursing a green sandwich, as he called his bottles of Heineken. As he proved, he could also be straight to the point…

“Say Dan, you want to help me get L’il Iolaire round to English Harbour?”

“Sure Don, when?”

“Now.” He was already up and out of his chair, gathering a chart and a couple of other things; he’d been navigating on a J-Class yacht – one of several sources, of his income.

Less than two minutes later we were in the dinghy rowing out to the 27ft 8in (8.4m) 1964 J Francis Jones yawl, quietly riding to her anchor. I made to get out but Don was already half on deck handing me a rope attached to the stem and stern of the dinghy.

“See those two knots, Dan? Just put this snap shackle between them.” The thing appeared in front of me. A few seconds later the oars and I were out of the boat and Don, having taken the sun awning down, asked me to winch the dinghy on deck using the mainsail halyard. In his typical way he’d had the winch handle extended with a second grip, making the work about twice as easy. Perhaps a minute later, if it took that long, the dinghy was hoisted, flipped and secured across the coach roof, the shackle was snapped back on the mains’l head and I was unpacking the jib from its UV protective slip, along the foredeck stanchion wires.

“Sailmakers hate me!” Don’s weather-beaten words explained from aft as I unzipped the bag, “I protect my sails from sun damage… even if they’re only down for half an hour.”

I looked back and Don had already hoisted the mizzen… Cripes! Smarten up! Some more seconds saw the jib hoisted, and I was astride the foredeck watching the anchor rope smoke its way off the white sandy bottom, before hauling the hook in over the stemhead.

“C’n y’ hold the jib out to port, Dan?” I stretched my arm out beyond the shrouds keeping the jib out while Don held the mizzen out to starboard. We’d been wind-rode so the breeze was dead ahead, and we were soon moving nicely astern. Don steered with his foot on the tiller as we wove our way out backwards through the anchored fleet, many here assembled for classics week. In clear water Don put the helm down and the wind came over the starboard beam. Under mizzen and jib we headed out of harbour. My next job was to look in a locker where in normal boats you’d find an engine. It was a mini cooler and two green bottles came out and went into the soft cooler sleeves either side of the cockpit. With a beer in his hand Don let me take off the mains’l cover and with a little wiggle to windward, just short of the harbour entrance, it was hoist and L’il Iolaire was under full sail as we passed the points and lifted to the rhythm of the cobalt Caribbean sea.

I should have timed it. I’d be surprised if from club seat to sea it was anything more than ten minutes.

Don’s gatling gun staccato bar chat had subsided into a monosyllabic bare necessity of communication, and a deep sense of calm enveloped the boat, as his Tilley-shaded eyes watched the sails, the weather and the sea.

Occasionally, with a similar economy of speech, he’d calmly explain something, like why we were tacking now rather than getting closer to that bluff – where the wind often dies. Incidentally we always also tacked the Heineken, with the helm’s to windward. A few other gems of pilotage were bestowed before we were heading into English Harbour and getting the main down.

Then we did everything again, in reverse order, sailing the anchor in while making two or three knots astern ’til we brought up handsomely right next to Admiral’s Inn. With the sails zipped, awning up, and all squared away we dropped the dinghy and rowed the few feet ashore, about ten minutes before darkness – the complete canopy of a Caribbean night – fell.

It was one of the most lovely little sails you could have, even compared to sailing down moonbeams in your childhood. And it was special to see Don in his element, his wandering sailor’s soul quiet, with that touch of reverence you can feel, as you take in the salt of the sea.

And it’s hard to believe that he’s dead. He died on May 1st, unexpectedly, but naturally, at home in Glandore, Ireland – where he’d kind of refused to retire, and kept his beloved 1933 Anker and Jensen Dragon Gypsy on a mooring.

A few weeks before we’d been talking, making a loose plan about me coming sailing – I knew quite a lot about the Dragon, Don had written articles about what great value a boat like that was for a beginner sailor, and how he’d sailed her to the first Brest festival in 1992. The fact he was still sailing her, he was due to be 94 in July, was such a joyous and inspirational idea; I thought I might be able to write about it too.

After his funeral, talking to his third son Ted, I heard Don had got Gypsy all ready to sail this season. “All bar the rig,” Ted said. “So my brothers Donald III (D3) and Richard, got her rigged and we anchored her off the church.” Don had sailed Gypsy for 38 years, and in 2019 trucked her to San Remo in Italy for the 90th anniversary Dragon class regatta. Easily the oldest boat in the fleet, out of 165 starters he said there were 71 boats behind him!

Gypsy is the last of three wooden boats he’d kept for many years. L’il Iolaire was lost in Hurricane Ivan on Grenada in 2004. Don sold the original Iolaire, (see below) which gave her name to the Imray series of Caribbean charts, in 2010. Sadly she was lost after an accidental gybe off Ibiza in 2019.

Don bought the 48ft (14.6m) yawl in 1957. She was built of pitch-pine and teak on oak frames as a gaff cutter in 1905 by the Harris Brothers, of Rowhedge on the Colne. He threw her engine overboard a year or two later, thereafter saying the best thing to do with an engine was tie a buoy to it and use it as a mooring.

A native New Yorker, Don had learned to sail dinghies as a young teenager on Manhasset Bay, Long Island. After a spell in submarines in the Navy, during the Korean war – a formative period in his life to which he would often refer, he read American History at University in Washington DC. Avoiding the family trade of insurance broker – his father worked in the “canyons of New York” and his grandfather did the same in Chicago, Don got a sailing job on the Abeking & Rasmussen 1953 54ft yawl Ondine, owned by Sumner ‘Huey’ Long. The boat was moved to Europe for the 1955 Fastnet, and Don became “skipper” at 25, but wasn’t being paid, so in Cowes he jumped ship to the Lloyd’s yacht Lutine, a 57 ft Laurent Giles yawl built in 1953. It was the eve of the Fastnet race and Jack Giles was also sailing aboard. “He spent the whole race telling us all that was wrong with her,” Don recalled. “Yet I still think Lutine was the finest boat he ever designed.”

At the end of the season he left Lutine for the Caribbean, sailing aboard a 46ft ketch – as cook. It was the first of 11 Transatlantics – seven with his own Iolaire. After a year doing various boating jobs in the islands Don was home considering another job in the canyons of NYC. But his father had had to retire at 55 after two heart attacks. It seemed like something snapped and he flew south back to the Caribbean landing in St Thomas where, by luck he landed a job of land surveyor. Having blagged the job he read up on it and was soon gainfully employed. The next thing was to buy a boat and he met a man with three who sold him one. That was teak sloop Iolaire and he got her for $3,000 plus $1,000 a year for the next four years, with no interest or repossession clause. It was 1957.

He began chartering, which naturally led to exploring and then surveying waters that had never been properly surveyed. Important ports and seaways were surveyed by Navies and for trade, but most areas had been ignored, or left to local knowledge. He made notes on existing charts and wrote up his findings which soon turned into a guide and articles in sailing magazines; his first article was for Yachting in September 1964.

Before this Don had considered he was not a good enough writer to be published. However during one his charters he recalled happening to end up sitting next to the recent Nobel prize winning author John Steinbeck, at dinner in Caneel Bay on St. John. As Don told it, Steinbeck listened to a few of his stories and said: “Kid, you tell a good story. Why not try writing?” When Don replied he couldn’t spell or punctuate, Steinbeck exhorted: “Well what the hell do you think editors are for?”

Also, through his Lutine/Lloyds links, he began consulting and broking insurance for yachts, which became a lifelong trade. He insured many interesting yachts, including Bob Dylan’s.

Don was a gleaner of all things boat and boatwise. Aboard Iolaire he could name where everything came from; these winches came from this boat, that one was unwanted in a yard. Even the wire wouldn’t necessarily have come from a chandler. It was maritime version of Johnny Cash’s 1976 automobile song One Piece at a Time, and while it looked a bit scruffy, it all worked pretty well… in much the same way as the skipper.

He converted her to yawl rig. The pine mizzen, Don was most proud to say, he took off Ondine when she was wrecked off Anegada Reef in 1960.

Don got married and his daughter Dory was born in 1963, however tragedy struck when his wife Marilyn was murdered by burglars when Dory was just 20 months old. Worse still Marilyn was pregnant with their second child. Dory went Stateside to live with Don’s sister Patty and Don went aboard Iolaire. He didn’t speak for three months, only coming ashore for the basic supplies.

It would be five years before he met Trich on a beach and began living a life split between Glandore, in Cork, Eire and his beloved Caribbean. As well as Dory they have three sons, Donald III, Richard and Ted – ten years younger than Richard and born in 1980.

By now Don was a well-known author. His 1964 book A Cruising Guide to the Lesser Antilles had opened up cruising in the area and his compendium The Ocean Sailing Yacht (1973) sold 100,000 copies. In 1979 Willie Wilson of Imray agreed to produce a set of charts using Don’s knowledge called the Iolaire series. These were very successful until some dodgy shops bought photocopiers and began selling them cheap.

Nevertheless in 2024 the Imray charts are still going and will continue to have the Iolaire title, and produce some royalties, as long as Don’s descendants carry on updating them.

Don had become the expert on the Caribbean, so much so that when the United States decided to invade Grenada in 1983 (after the communist coup in 1979), they contacted him to seek advice on where to drop a group of Navy Seals. Don turned up for this meeting at an airport but wasn’t met despite being in his uniform of Tilley hat and red trousers. In the event four Seals drowned and their bodies were never recovered. As an ex-navy man and patriot Don was horrified 30 years later when someone involved turned up, showed him where they were dropped and Don knew it was one of the worst places they could have gone in the water.

If ever there was a man for a plan, Don was it. One of his mottoes was: Worry is like a rocking chair, you’re doing something but it doesn’t get you anywhere; always make a plan and move forward.

In 2004 Don gave a talk on the Classic Boat stand which I was organising at the London Boat Show, newly moved to Docklands. He had a wide range of talks and spoke at a few of our events, illustrating for people how to veer extra anchors when expecting a hurricane for instance.

In 2005 in her 100th year Don asked me to help him sail Iolaire from Cowes to Limehouse in London, for her winter berth. I’d be one of five crew in the seven-berth yawl.

Sailing without an engine makes you a more circumspect sailor. Keen for an early start from Cowes, heading up-Channel for the London River via the notorious Goodwin Sands, we were dismayed by an almost complete lack of wind. At our mooring off West Cowes yacht basin the tide was running out fast, and we let go of the mooring we would not be able to clear the yachts moored aft of us. We watched for everything, the first signs of the tide slowing, the first breath of air in a baby-blue September morning. Eventually Don called the harbourmaster, a deal was made, and we could get a tow out into the roads. Even there, with all sail set, plus a lightweight mizzen staysail, we could only stem the last flow of tide.

It was like the rest of that summer… too little wind or too much. One long-term forecast had predicted Force 5 southwesterlies. But, with high pressure around, the Met Office was stymied, and we had a zephyr from the south rather than the day’s predicted northerlies. So we started into the tidal drag, stemming it and then using it and finding Boulder and Street – Don’s own buoy! – that mark well-known short cut of the Looe Channel.

Don Helming Iolaire passing the Street buoy on the Looe Channel

Don eschewed lunch for his “green sandwich” – and set our watches. We’d four hours on with six off, with the five of us (Don, John, Claymore, Chris and myself) staggered for a fresh person to come on deck every two hours. It worked well the first night, though when I came on deck at one point we were pointing west again, off Shoreham, a mistake that came of following the wind, on the cheek as it were, while it backed around the compass to north.

By 0400hrs we’d picked up Beachy Head light, but we still had Royal Sovereign – a few miles east  off Eastbourne – in sight when we had an American breakfast: Don’s homemade pancakes… cooked in bacon fat. Bacon and pancakes with maple syrup was his regular American staple. And why not? There was also plenty of good tea – he’d lived in Ireland many years after all!

The northerly airstream was strong enough to hand the light-weather sails and we had our yankee (large high footed jib), staysail, main and mizzen set as we passed Dover. The GPS, a handheld Garmin, gave up. It was giving us previous fixes in any case. With night coming on, it made sense to go outside, or east of the Goodwins, and with the wind where it was, plus a few hours of tide left, we could clear them, or the worst of them, by midnight.

Of course the wind came a point east, forcing us to tack up the stretch of water between the S and E Goodwin lightships and against the west-going shipping. The wind rose to a Force 6, gusting high sevens, and, with tide against us now, we made a mile if that – north each tack, the turbulent seas threw our bows off. Rain and the odd bit of fog passed. Iolaire felt in her element, though she needed pumping out every 40 minutes as she worked in and out of shoals. Occasionally she tossed a bit of spray over her deck to cool us down and we settled in for a long night.

I was going to stay on deck at any rate; the sheer number of charted wrecks around the infamous sandbanks off South Foreland in these busy waters was a good incentive to stay alert. And I was thinking I was getting a bit of salt, and what a good place it was to be, compared to the office… But of course the epithet of an old salt would be reserved entirely for Don the skipper, who, at 75, chose to stay awake through the dark hours as well, hunkered over the helm of his beloved Iolaire, while I did the sheets and pilotage, calling the tacks as we hit the 5m contour. Even in the surf she came round like a dinghy; never faltered once.

As the tide abated later I didn’t want to call the tack to Don to steer out into the North Sea again and we were on clearing bearings to skirt the charted drying heights of Goodwin Knoll. We were right on the bearings and I called depth to Don as we tracked the 5m contour, once or twice even shallower than that. I hadn’t been able to find a transit, so the hand-bearing compass earned my love and respect that night.

Compared to being guests of the Goodwins where so many have outstayed their welcome, the run-up Father Thames, starting in what can only be described as an ochred  Turneresque tableau of dawn, was clean, fast and without incident, taking 12 hours from a three-point fix north of Margate.

The wind obeyed our every need, even allowing us to goosewing through the Thames Barrier, and only fell off to disinterest as we neared our destination. A tow from a friendly yacht then put us into the basin, or rather close to it. Slipping our bow rope we trusted the momentum of Iolaire’s massive keel to get to within a few feet of the Limehouse Basin entrance in front of the lock gates. I had a lightweight line ready with a heaving line knot in the end for some weight and stood at the bows addressing the steady line of lycra’d City joggers coming round the Thames waterfront path and crossing the little bridge in front of us. “Hi, can you take a rope? Excuse me can you help us? Hello! We have no engine here could you take a rope?”

The reaction was either look away in horror or pretend not to notice: no help from Lycra. Seconds were rolling into minutes and the young ebb was beginning to snatch at the aft end of Iolaire’s keel. Don was explaining the situation to the harbourmaster on the VHF: “We can’t tie up! We can’t reach it. Somebody needs to take a line.” He had the cranky weariness of someone having to constantly explain why things are as they are. Eventually the HM arrived at a marching pace and I still think that was my all-time personal best-heave of a heaving line. We warped in, thankful that there was no need for anchoring and dinghy antics this day.

Looking back I realise what a treat it was to be sailing Iolaire in waters like that, in her 100th year, pretty much without technology but with an excellent buoyage system in which to keep trust. She was the boat that gave Don the wherewithal to open up the Caribbean, making sailing safer, no doubt saving lives. She’s in Davey Jones Locker now and he’s in some celestial chartroom… where no doubt the angels are saying to each other: “If you want him to stop talking, then just go sailing with him.”  ©DMH