Little Compass RoseCaribbean Compass   October 2019

Remembering Iolaire

In early 1919, a 190-foot British Royal Navy steam-powered yacht named Iolaire struck rocks during bad weather and sank off the port of Stornoway in Scotland. Over 200 lives were lost. Just over one hundred years later, another yacht named Iolaire struck rocks during heavy weather and went down. This Iolaire, a 46-foot engineless wooden yawl launched in 1905, sank off Ibiza in Spain, fortunately with no loss of life.

The eye-catching red-hulled yawl Iolaire was famous in the Caribbean, having been raced and cruised by author Don Street for half a century until he sold her in 2009. Under her newest ownership, Iolaire had been running dead downwind close to shore when an inadvertent gybe drove her onto the rocks on July 26th, 2019 — coincidentally Don Street’s 89th birthday. In another coincidence, Don’s son Mark, who grew up aboard Iolaire, was then skippering a motorsailer in Ibiza and from the scattered debris confirmed the demise of his childhood home, a shattering experience.
Thus ended the career of a 114-year-old classic yacht that, except during the World War II years of 1940 to ’45, had been in commission every year of its life.

The Early Years
Iolaire was designed as a gaff cutter and built and launched by Harris Bros, UK, in 1905. She raced successfully from 1909 to 1923 for an Irish family, the Tweedys. Iolaire was later raced and cruised by several prominent skippers of the UK’s Royal Ocean Racing Club, including ocean-racing pioneer Bobby Somerset from 1946 until 1955. Somerset sailed her in 14 days from the Cape Verdes to Barbados, and cruised extensively through the Caribbean as far west as Jamaica.

In 1951, Somerset sailed Iolaire from Kingston, Jamaica, to Cowes, UK, direct. Two of his crew were young American university students, Cory Cramer and Peter Stamford. Peter wrote and sold his first article, “From the white sands of Jamaica to the white cliffs of Dover,” to Rudder magazine and went on to found South Street Seaport in New York City. Cory became the founding director of the Sea Education Association (SEA), an internationally recognized leader in ocean education based in Woods Hole, Massachusetts. SEA’s 134-foot sail-training brigantine is named Corwith Cramer in his honor. The ship hosts voyages throughout the Atlantic Ocean, including ports of call in the Caribbean islands.

Somerset was responsible for changing Iolaire’s cutter rig from gaff to Marconi — he had inherited the Marconi rig from German Freres’ Joanna, when Freres had Camper & Nicholson build Joanna an aluminium mast.
Somerset sold Iolaire to a retired US Navy captain, Bob Crytzer.

Rebuilding a Write-Off
A 26-year-old Don Street arrived in St. Thomas, USVI in 1956, and found work as a land surveyor. Bob Crytzer met Don and recognized him as an enthusiastic young sailor who would take good care of Iolaire. He offered to sell Iolaire on terms Don could not turn down — US$3,000 down plus $1,000 a year for four years, no interest and no repossession clause — so Don bought her in March of 1957.

Unfortunately, as a result of a broken anchor shackle, Iolaire went on the beach in Lindberg Bay. Bilged and lying in 18 inches of water, the boat was deemed a write-off. Don bought Iolaire back from the insurance company, as is, where is, with the responsibility of removal, for US$100. He got her off the beach, put her on the West Indian Company dock in Charlotte Amalie, and set up a mini-shipyard. He replaced four frames, five timbers, a bilge stringer, eleven planks and the rudder, and put in a new main cabin interior. Iolaire was off on charter 13 weeks and three days after Don bought the wreck on the beach.

During the rebuild, Don also re-installed an engine — “a big mistake,” he says. “Iolaire sailed so well that we very seldom needed it, except to generate electricity. It was a 20-horsepower gasoline Seascout (I think they were ponies not horses), driving an offset propeller through a rather inefficient belt drive. After about ten years of fighting the engine, we’d used up time, money and energy and gotten so frustrated that we took it out and dropped it in the lagoon at St. George’s, Grenada, with a chain on it and a buoy on the end. It made a good mooring. Where the engine had been, I built a chart table that has produced nine books and a couple of hundred magazine articles, so I think it was a fair trade.”

Why a Yawl?
Don also converted Iolaire to a yawl rig. He recounts: “With her big mainsail and small headsails Iolaire was fast but had such a god-awful weather helm that anyone who sailed Iolaire for any amount of time looked like an orangutan: their arms had been stretched so much that their hands were in the region of their knees. Since that time, with judicious re-rigging, Iolaire is now so well balanced that my wife Trich, who weighs about a hundred pounds, is our best helmsman.

“On Iolaire we had no running backstays on our mizzenmast, despite it being stepped on deck. We had salvaged it from the wreck of Ondine. When setting up the chainplates to step Ondine’s mizzenmast on Iolaire, I remembered reading in one of the late Uffa Fox’s books that if a shroud is given one inch of drift (distance aft of the mast) for every foot of height, the shroud in effect becomes a stay (a shroud supports a mast athwartship, a stay supports a mast fore and aft). So, to be super-safe, I set the upper shroud chainplate 36 inches aft of the mizzenmast. Everyone said the mizzen would go overside, as at times it shook like an Egyptian belly dancer. But even without backstays Iolaire’s two mizzen staysails — one of 350 square feet, and a big one of 650 square feet used when wind was almost dead aft — never managed to pull down Iolaire's mizzen. Uffa Fox was correct.”

A Family Boat
Don Street tell us, “In the early days of chartering, the Antigua fleet did not want to go the Virgins because of the long beat back from the Virgins to Antigua. Similarly, the Virgin Islands boats did not go down islands as they we unwilling to beat to windward across the Anegada Passage. Iolaire was the only boat that was willing to do this, which gave us a number of down island charters that allowed me to start exploring all of the Eastern Caribbean. While approaching an anchorage I was frequently asked, ‘Skipper, what will we find in this anchorage?’ All too often I would have to reply, ‘I don’t know; I have never been here before and there are no cruising guides. We are exploring!’

“In 1963 I conceived the idea of my book A Cruising Guide to the Lesser Antilles. My late first wife, Marilyn, had learned to sail in a hurry. We sailed Iolaire by ourselves, with our infant daughter, Dory. (Dory was on the Round St. Thomas Race at age 29 days. Mommy took time off on the downwind leg to nurse her.) The three of us explored the islands, often making long passages in rough weather. Even under storm sails, Marilyn stood her watch, cooked and tended Dory. In port, with the charts spread out in front of me, file cards on top of them, and the typewriter in my lap, the main cabin of Iolaire was uninhabitable for weeks at a time. Yet, instead of complaining, Marilyn plied me with hot coffee in the mornings and cold beer in the afternoons, and with gentle prodding and smiling encouragement kept me going.

“The east coast of Martinique is frequently described as ‘too dangerous’ to visit. Hell — Marilyn, Dory and I, with our schipperke dog Merde, explored the east coast of Martinique in the early Sixties, the first foreign yacht ever to visit. We spent a week there, dodging reefs and entering and leaving harbors under sail, despite the fact that often the channels faced directly into the Trades.”
After Marilyn’s untimely death in the early Sixties, Don met “a cute little Irish girl, an Aer Lingus stewardess” who was visiting a friend in Carriacou. “I asked Trich to sail with me. The two of us sailed Iolaire to Martinique. On the way back south we anchored just at dusk between the Pitons, in those days an uninhabited coconut plantation. The only sounds were tree frogs. As we were having our after-dinner drinks on deck, a great big harvest moon appeared between the embracing Pitons, making it the most fantastic anchorage in the entire world. I think Trich agreed to marry me as she figured that was only way she would ever see this scene again.

“The two of us chartered Iolaire for a year and Trich developed into one of the finest light-weather helmsmen I have ever sailed with. An awful lot of exploration was done with me standing on the spreaders, giving hand signals to Trich on the helm.
“In the late 1970s, when the People’s Revolutionary Army took over all of Calivigny Point in Grenada where we had our house, we lost everything. For the next few years we lived part time on the boat, with our new sons (we have three boys: Donald the Third, Richard and Mark) and Dory, now a teenager, and part time in Ireland in a house Trich had inherited. Trich convinced the Irish schoolmaster that if she took the boys out of school from Christmas until Antigua Week and she tutored them aboard, they would catch up when they got back to Ireland.

“In all the years that I raced Iolaire, Trich was with me almost all the time. She missed one Antigua Week as she was producing Mark. But Mark sailed the next Antigua Week at age one year, in a straw basket swung from the overhead. And Richard, our middle son, came on his first race when he was 11 days old.”

Iolaire’s Adventures with Don
In 1962 Iolaire was dismasted in the Anegada Passage but Don managed to tow the mast to Norman Island, lift it on deck, power back to St. Thomas, scarf 12 feet onto the bottom of the mast and be out on charter 11 days later.
In 1966 Iolaire lost the top ten feet of her mainmast off Dominica. Don, the then four-year-old Dory, and a young Grenadian crewmember sailed Iolaire under jury rig to Grenada, 200 miles, averaging 5.2 knots. A bare aluminium tube was shipped to Grenada, fittings were transferred from the old wooden mast, and new rigging was made. Iolaire was back sailing two months later.

In 1984, Iolaire was caught by the late-season (November 6th) Hurricane Klaus while anchored on the north side of St. Martin, which became a lee shore. Don recalls, “I kept Iolaire off the beach by systematically deploying six of the seven anchors we carried onboard. As the wind veered and the load came on the starboard anchor, the port anchor line would go slack and I would then drop another anchor, and then veer more line on the anchor that was taking the load until the anchor just dropped also picked up the load. I would then secure both lines so Iolaire was once again riding on two anchors. Despite the fact that during the hurricane the wind switched through 180 degrees, Iolaire was continually riding on two anchors set in a ‘Y’. Thank God for her seven anchors!”

He continues, “Then, from 1985 until I sold her in 2009, Iolaire had six almost-disasters. Three times disaster was avoided by the skilful work of crew and skipper, and three times Iolaire was saved by her own lucky streak. In one incident, in 1995, were hove to in a gale 300 miles west of the Azores, with the crew enjoying a roast beef dinner with all the trimmings on her gimbaled table. We suddenly discovered a bilge full of water. We immediately started pumping on our single-acting, 30-gallon-per-minute Edson diaphragm pump. We cleared the bilge with no trouble. After much searching and moving of gear, we discovered the leak was from a stem bolt (subsequently discovered to be broken) in the forward part of the stem, the only area of Iolaire not worked on in her 1994-95 rebuild. By pumping ten minutes out of every 30, the bilge was kept clear. We pumped for 48 hours until we reached Horta.”

Don notes that when Iolaire was hauled in 2005, the mast was pulled for checking, the bilges were completely emptied and water tanks and internal trimming ballast were removed; the iron work, mast step and floors in the forward part of the bilge were cleaned, chipped and painted with coal tar epoxy; and new batteries were installed.
Iolaire was painted red for over 50 years. Don says, “When I purchased Iolaire in 1957 she was red. I accused the previous owner of painting her red to hide the rust stains from the iron work whose galvanizing had long since departed. Through the years I eliminated all the iron fittings but kept the color, as she had become famous as ‘the old red race horse.’”

Don is Unsinkable
For half a century, Don Street cruised, chartered, raced and explored aboard Iolaire. With her as his vehicle, home and inspiration, he wrote cruising guides to the Eastern Caribbean from Puerto Rico to Venezuela, the books Seawise and The Ocean Sailing Yacht, and countless magazine articles including several long-running series for Caribbean Compass. His explorations resulted in the Imray Iolaire charts of the Eastern Caribbean and the Atlantic islands. Iolaire drew a deep 7’3”, and as longtime editor of Sail magazine, Patience Wales, said in the 2001 reprint of Don’s Caribbean cruising guides, “Street was the first; ever since 1964, all other guide authors have just followed in Iolaire’s wake, avoiding the rocks and shoals that Street and Iolaire discovered.”

Don sailed Iolaire roughly 200,000 miles, in all conditions. Considering the extensive cruising done before her final owner bought her, she had probably done between 300,000 and 350,000 miles in her lifetime.
Meanwhile, Don sails on. “Gypsy, my 86-year-old Dragon, is the oldest Dragon in the world still racing — with myself at 89 the oldest Dragon helmsman in the northern hemisphere. As of this writing we plan to go to San Remo in Italy to join over 150 Dragons celebrating the class’s 90th birthday from October 5th to 13th.”

Rig a Gybe Preventer!
by Don Street

I believe that the loss of Iolaire could have been prevented if an aptly named “preventer” had been used. In addition, every year a number of sailors are killed, and a large number injured, by inadvertent gybes. So, when sailing downwind, a preventer from the end of the main boom to the bow should be rigged. This should be done before leaving the anchorage.
When I bought Iolaire she still had her heavy 24-foot-long main boom, left from her gaff-rigged days. I realized that an inadvertent gybe could be a real widow maker. When running down wind I always rigged a main boom foreguy preventer. Originally it had been a difficult operation, but was simplified through the years as described below.

It can be done in one of two ways: using a temporary emergency rig or using a permanently installed Iolaire-style combination anti-gybing and reaching sheet rig.
For the temporary emergency rig, take a line at least the length of the boat, secure one end to the end of the main boom. Secure it to the mainsheet bail if it is end-of-boom sheeting. If it is mid-ship sheeting, make up a strong strop of nylon webbing, secure it to the end of the boom, and secure the end of the line to the strop. Pull the line tight along the bottom of the boom, tie it off at the gooseneck, and coil up the excess.
Once you start sailing and you are broad o
ff, over-ease the mainsheet, disconnect the line from the gooseneck, take it outside the rigging, secure it to a cleat or anchor windless as far forward as possible, pull it tight, then tighten up on the mainsheet.
Thus secured, it is almost impossible to do an accidental gybe.
To install the permanent Iolaire combination anti-gybing/reaching sheet rig, obtain a becket block with a swivel on it, a length of wire about two feet shorter than the length of the boom, and a sheet three times the length of the boom. Secure the becket block at the end of the main boom. Secure it to a bail forward of the mainsheet bail if end-of-boom sheeting. If mid-ship sheeting, make up a strop of nylon webbing as previously described. Secure one end of the wire to the becket on the becket block, attach a light line to the other end, run the light line through the tack eye on the main, and lash the wire tightly along the bottom of the boom. Make up a reaching sheet three times the length of the boom, thread it through the becket block, secure it to the gooseneck, and coil up the excess line. Rig spinnaker pole foreguys permanently port and starboard, and secure both ends of the foreguys to a stanchion as close to the main shrouds as possible.

When reaching, disconnect the reaching sheet from the gooseneck, attach one end to the clew of the headsail, run the other end through a lead block on the caprail fairly near the shrouds, then back to a cockpit winch. Take the strain on the reaching sheet, ease the genoa/jib sheet, and the angle between the headsail and mizzen is opened out. The backwind on the main is eliminated, enabling the main to be eased, lessening the heeling angle and weather helm, plus increasing your speed.
As the wind gets farther aft, on the quarter, disconnect the wire from the gooseneck, slack the lee pole foreguy, take it outside the rigging, connect it to the wire, over-ease the main, take up on the foreguy, secure it, then re-trim the main.
Set up in this fashion, the chances of an accidental gybe are eliminated.

When the wind gets so far aft that the headsail is collapsing, take the reaching sheet off and wing out the jib on the other side, and sail “wing and wing.” Even if you do not carry a spinnaker, I feel a spinnaker pole to wing out the jib is an essential part of equipment for any boat cruising the northern end of the Caribbean, because from Antigua north, courses are mostly either dead to windward or dead downwind.

Regarding an easily rigged and effective boom vang that does not load up the boom or gooseneck, see my website The gear described does work. We developed it aboard Iolaire in the late 1950s and used it with great success for over 40 years.

Visit Don Street’s website at for seamanship tips, hurricane advice and a wealth of other information.

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