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How to be a Charter Pirate

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Mocka Jumbies and Rum...

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It ain’t easy being a charter pirate. You seldom have a buck to spare in your pocket, your clothes are salt-stained and your boat has got a bad leak in the basement. But you earn money taking people sailing which sure beats working on land.

The late Fifties and early Sixties saw only a dozen or so charter boats based in St. Thomas, a few more in Antigua and barely a pocket-full in the Grenadines. As chartering became a steadier way to make a living, the fleets grew and so did the size of the boats.

Destination: Sailing the U.S. Virgin Islands

By 1968 in St. Thomas, most of the charter boats were owner-operated and their accommodations more suitable for landlubbers mostly from the States. For instance, there were occasionally double beds, well, mostly three-quarter size, and two heads, one for the guests, the other for the crew. Quite a few boats had a generator for all those nice conveniences – frig and freezer for cold beer and running water for a below-decks shower.

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The charter boats came in all flavors. Many were old wooden classic yachts. They were predominantly schooners and ketches from 40 to 72 feet. About half of the 45 charter boats seriously working in 1968 could take up to six passengers. Average costs for two couples for a minimum of five days was from $36 to $53 per couple per day. Food and drinks were tacked on but by the Seventies, prices were raised to include all meals aboard with standard bar drinks and wines.

Being a Key West “Local” Has its “Quirks”

Marinas and haul out facilities popped up. The Sheraton built a hotel beside Yacht Haven Marina, which expanded to three docks with a restaurant/bar on the second floor. On the lower level beside a fuel dock was the marina office and the Virgin Islands Marine Radio, WAH, operated by Bob Smith with his wife Dorothy who also ran Ocean Enterprises, the first clearing house. Services provided by diesel and refrigeration mechanics, riggers and sail makers, became a godsend.

The crews changed, too with most of them married couples or those not yet “churched” and only a few single guys working with a cute chick to cook and…er, rub down the rail. These were passionate people, willing to give up a “normal life”, adventuresome and insanely fond of their boats. In order to sail among tropical islands, they were willing to share their gypsy-like lives with strangers, for a price.

Zen & the Art of Marine Diesel Maintenance

Hardly would you find a more individualistic and enthusiastic bunch as the St. Thomas-based crews. To name just a few of those who remained for many years, there was Ross Norgrove with his 65-ft wooden schooner, White Squall, Bill and Sue Beer with their 54-ft wooden schooner, True Love, Dyke and Inga Wilmerding with their 62-ft schooner Mandoo and later, Zulu Warrior, and Neil Lewis with his schooner Alexander Hamilton. Don Street was in the charter trade throughout the island chain with his yawl, Iolaire, built in 1905.

Saving Money by Doing Laundry on Board

There were several famous windjammers that worked the islands for years; Art and Gloria Kimberly on their brigantine Romance and Jack and Dee Carstarphen on their ketch Maverick.

It was a grand and fairly easy sailing life in the islands when nothing was too organized and strictly enforced as it is today. The charter skipper was supposed to have a U. S. Coast Guard license to carry up to six passengers, but that was about it. There were no mooring fees, insurance, gross receipt tax or anchor permits required. But the Coast Guard license was hard to get if you were blind in one eye.

My husband Mike who has only one eye had a hard time getting a waiver. Knowing that Fritz Seyfarth, who chartered his ketch, Tumbleweed was blind in his left eye and had a license, Mike asked him what he had to do to get it.

“Simple!” Fritz said. “When I read the eye chart with my right eye, I put my right hand over my left eye. For my left eye, I put my left hand over my left eye. No problem!”

The End Game

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