Part Three: The Dawn of the USVI Charter Trade
by Don Street
The folks who ran charter boats in the USVI in the 1950s and ’60s were a different sort than those who do so today.
In the late 1940s, a Bahamian sailor and adventurer named Basil Symonette wandered down through the Bahamas and Puerto Rico in his 43-foot William Handdesigned gaff schooner, Sea Saga, and ended up in St. Thomas, US Virgin Islands. After chartering Sea Saga for a couple of years, he sold her and took over the running of the fledgling Yacht Haven marina in the early 1950s.
Yacht Haven
Yacht Haven marina — which through the years, by purchase, development, knocking apart and redeveloping a couple of times, developed into what is now the deluxe IGY Yacht Haven Grande — came about after the end of World War II. The West Indian Company, which had been formed in 1912 as a coal-bunkering operation supporting vessels that would travel through the Panama Canal, owned all the land north of its commercial dock in St. Thomas Harbor. In 1952 the company discontinued coal bunkering.
The company had a large barge that had reached the end of its life, which they sank about 100 yards north of the commercial dock. They built a wooden pier out to the barge. On top of the barge they constructed a dock containing an office and about a dozen storage lockers. They installed lines for petrol and diesel running from tanks ashore to pumps on the dock. They also ran a water line to the dock.
Ashore they built a small building to house a marine store, another building for a small bar and restaurant, plus a small building with a couple of toilets and showers.
Yachts had started trickling in from the East Cast of the States. West Coast boats cruised the Pacific coast of Central America, working their way south to the Panama Canal. To rebuild their cruising kitties, they often managed to find work with the corporation that ran the Panama Canal. Many became tired of Panama, slowly worked their way eastwards and ended up in St. Thomas.
All boats arriving were short of cash. The skippers discovered that they could make money chartering their boats, either by the day or for one- or two-week charters.
The day charter business
That is how two of the most successful early day charter boats — Pat and Leo Minor’s Tropic Bird and Jack and Ruth Carstarphen’s Shellback — arrived in St. Thomas. Both couples were founding members of the Seven Seas Cruising Association (SSCA). Their boats were almost sister ships, both 36-foot Block Island ketches with pinky sterns, making them 40 feet long overall with good deck space. One year, the Christmas winds came in with a vengeance and Shellback blew out her main. Obtaining a new mainsail in the ’50s in the Virgin Islands was a four- to fivemonth project. But Tropic Bird had a spare mizzen, which she lent to Shellback. It was only slightly smaller than Shellback’s reefed main, and the wind blew so hard all winter that it worked perfectly.
For drumming up day charters, it was a case of the skippers visiting the hotels, meeting guests and letting them know that they could have a nice day sail to a beach on St. John with lunch, beer and drinks thrown in — all for just ten dollars per person. This was possible because if the skipper brought an empty gallon jug to Reese’s liquor store he could fill it up with St. Croix rum for 75 cents, and a case of 24 cans of Schaefer beer cost less than two dollars.

The VI Hilton had been built in 1950 on a hill overlooking St. Thomas. It was a large hotel built with the expectation that gambling would be allowed in St. Thomas, which never happened — quite. Entertainment at a small bar was provided by the calypsonian The Duke of Iron, famous for his version of the ribald classic “The Big Bamboo.” People could not figure out how the owner could pay such a famous star on its proceeds. What they did not realize was that in a back room there was a nightly high-stakes poker game, and when his show was over The Duke of Iron would join it. The hotel owner was an excellent poker player and would relieve The Duke of the majority of his earnings, leaving him enough to get by on until the next night.
Among the hotel guests were many women who had come from the US mainland to obtain divorces in the St. Thomas court. It was a federal court, so their divorces could not be contested in any state court. However, they had to establish St. Thomas residency, which took six weeks. That, plus organizing a lawyer, scheduling a hearing, etcetera, often took months, so the women got bored and restless, presenting a great potential charter clientele.
Two good-looking young sailors, Rudy Thompson and Eric Winters, obtained the use of Tropic Bird when Pat and Leo Minor landed a job running a big powerboat.
In the early ’50s steel bands were just arriving in the USVI, but bongo drums were still popular. Rudy and Eric would go to the VI Hilton, one would play the bongos and, as a crowd assembled, the other would do the sales pitch for a day sail. Lining up clients wasn’t a problem.
As they sailed out of the harbor, once clear the harbor mouth, Rudy and Eric would shed their clothes and announce, “Everyone sails naked in the Caribbean!” often with the hoped-for results. Sometimes, sailing to windward with the boat well heeled over, one of them would take the spinnaker halyard, stand up on the bow pulpit, swing out over the water and land on the stern. Very spectacular, and the ladies enjoyed the show, but as Eric said, “Once in a while instead of landing on the deck you’d end up being wrapped around the mizzen rigging, which was very painful.” They had one good season but then Pat and Leo’s job on the motorboat ended, and Rudy and Eric eventually acquired wives, gave up chartering, and ended up working ashore.
The term charter business
Some boats started taking charters of one week, ten days, or occasionally two weeks. These charters were usually limited to the waters around St. Thomas and St. John. A two-week charter might sail south to St. Croix and back.
Most charters didn’t venture farther east than The Baths on Virgin Gorda, as the standard chart was the US coast and geodetic survey 905, which covered only the area from the west end of St. Thomas to the west coast of Virgin Gorda and south to and including St. Croix. (See sidebar.)
Other than my Iolaire, none of the St. Thomas charter boat fleet was willing to fight across the Anegada Passage to St. Martin, St. Barth’s and on to Antigua. In 1962 I deadheaded directly south to Grenada to pick up a three-week charter, sailing back north through the islands to St. Thomas.
This convinced me that this was the best way to see all the islands in the Eastern Caribbean chain (see the December 2021 and January 2022 issues of Compass in the Back Issues Archive at www.caribbeancompass.com). Later, Ross Norgove with White Squall II, and Jim Squier with Te Hongi followed my lead, picked up charters in Grenada, then headed north through the islands.
The St. Thomas charter fleet was different from Nicholson’s Antigua fleet, as the majority of boats were 50 feet or under. With very few exceptions they were owner operated until the late 1970s, when wealthy owners in the States would send down bigger boats with hired skippers. These boats were very much resented by the owneroperated boats. The owner-operated boats had to be self-supporting, but if the
skippered boats lost money chartering the owner just deducted the loss from his income tax.
Some of the boats, though good sailors, were a bit long in the tooth. Some were schooners built in Maine or Nova Scotia in the 1930s, during the Depression, and iron fastened. Gitana, a 46-foot Nova Scotia schooner, was skippered by Hardy Wright — an unfortunate name as, although he was an excellent sailor, he was often referred to as “hardly right” or “hardly ever right.” One day while washing dishes he inadvertently dumped some of the cutlery over the side with the wash water. When he dove to pick it up he decided to check Gitana’s bottom to see whether it needed scrubbing before the Memorial Day weekend races from St. Thomas to St. Croix and return. He discovered to his horror
that the iron ballast keel was about two inches below the wooden structural keel. Obviously the keel bolts were broken. He took three dock lines, looped them under the boat, tied the ends together and, using a Spanish windlass, tightened them up bar tight. He then sailed carefully to Beef Island. When Gitana was hauled she settled down on her keel so nicely that you never would’ve known that old keel bolts were broken.
Augie and Lynn Hollen chartered their 45-foot Maine-built Casey schooner. Early one season the engine died. They did not tell the charter brokers and continued to accept charters. Charter parties would arrive, be greeted, shown around the boat and gear stowed. When the time came to leave the dock and the engine wouldn’t start, Augie would dive into the engine room and spend about half an hour. He then would emerge and say, ”I can’t figure out what’s wrong, but we can get underway under sail. Once we are anchored this evening I will attack the engine and get it going.”
They would sail off the dock and have a nice day sailing. Once anchored, awning rigged and charter party happily having sundowners in the cockpit, Augie would “work away” on the engine while Lynn cooked dinner and entertained the guests. Augie would “give up” by dinnertime, apologize for the nonworking engine, and say, “Oh, well. The boat sails so well we really don’t need the engine.” Lynn was a very beautiful gal with long red hair, a good sailor and a good cook. Augie, too, was an excellent sailor and a raconteur. They never had an unhappy charter, and
never told the charter brokers that the engine didn’t work.
Lynn went on to become a very successful charter broker. Augie settled in Coral Bay, St. John, built a 40-foot cowhorn schooner with a lug foresail that overlapped the mainsail. This sail had to be trimmed like a genoa on each tack. He persuaded several more sailors to build cowhorn schooners at Coral Bay, too.
A last Sea Saga story
Rudy Thompson, when he first arrived in St. Thomas and before his day charter days, took over skippering Sea Saga for Basil Symonette. Just before Carnival started one year Rudy booked a rather crazy charter. A couple had purchased a small guesthouse in Dominica, and wanted transportation for themselves, their grand piano and a big German Shepherd. As previously mentioned, St. Thomas charter boats seldom went east of Virgin Gorda, and Sea Saga, a gaff-rigged schooner, was not very good going to windward. But the only way to get the grand piano and the German Shepherd to Dominica was to charter a boat. Rudy was the only skipper willing to take on the charter, so he was able to negotiate a high charterfee, payable in cash before departure.

They took the legs off the piano, covered it with canvas and strapped it down on the cabin top. Rudy collected the cash, gave money to his crew and told him to stock the boat for the trip, and went off to enjoy Carnival.
Enjoy he did, never going to bed and arriving on Sea Saga at about 0700. They got underway, and once out of St. Thomas Harbor, Rudy brought Sea Saga hard on the wind and turned the helm over to the crew and charter party, who were moderately good sailors. He told them to just sail as close to the wind as possible and still keep the boat moving, and went below to sleep.
It had been a hell of a Carnival and Rudy slept for about 18 hours. He was woken up by the German Shepherd licking his face. He was pleased to discover that a norther had come in about the time they left St. Thomas. He saw St. Kitts to starboard, just a little forward of the beam and about ten miles to leeward. He eased sheets and headed directly for Dominica. They arrived in Dominica four days after leaving St. Thomas. He had booked the charter on the basis that it would take him ten days to island-hop to Dominica, and was a very happy skipper.
Meanwhile, Basil Symonette, who (according to a biography at www.wikitree.com/ wiki/Symonette-24) had been popular among a fun-loving gay crowd in Miami after WWII, met a handsome man from Chicago while standing in line at the St. Thomas airport. The couple fell deeply in love and became life partners. Together they eventually built a beach bar and five-cottage resort on Virgin Gorda that expanded
into the now-famous Bitter End Yacht Club.
Visit Don Street’s website at www.street-iolaire.com for more stories and other information.
Eastern Caribbean Charts from the Fifties to Now
It was practically impossible to buy paper charts in the Eastern Caribbean in the 1950s, and of course electronic charts were unheard of. There were just the bare beginnings of yacht chandleries in St. Thomas and Antigua, and neither kept charts in stock.

Chart 905 was available in St. Thomas, but to obtain other charts you had to send away to New York Nautical for US charts, or Kelvin Hughes or the British Admiralty for British Admiralty charts, and ask the price of the charts and also the cost of having them airmailed to you. A bank draft had then to be purchased and sent before the charts would be shipped. Airmail was not particularly fast, so from the time the first letter was sent to when the charts were actually in your hands was a month to six weeks, sometimes longer, or sometimes never when they got lost in the mail.
The US Virgin Islands were very well charted by the US Coast and Geodetic Survey corrected. He was rather embarrassed when I pointed out that the chart of St. Thomas Harbor marked “corrected to 1973” showed Ballast Island just east of Frenchtown. I pointed out that Ballast Island had been dredged out by the US Navy in about 1920, right after we purchased the Virgin Islands from the Danes!
In 1979 I signed a memorandum of agreement with the late Tom Wilson, head of the chartmakers Imray, to do yachting charts of the Eastern Caribbean. The charts were to correct all the errors I had found in the British Admiralty and US charts covering the area from St. Thomas to Grenada. The area from St. Thomas to Grenada is now covered by 20 up-to-date, accurate Imray Iolaire charts. They are so highly regarded that Navionics, C Map and many other electronic chart companies pay Imray a royalty to use the information from the Imray Iolaire charts.