Eight Bells: Donald Street, Jr.
Donald Street, Jr., 93, died April 30, 2024 in County Cork, Ireland. He spent his final day working on the 92-year-old Gypsy, readying her to be the first Dragon launched for the season.
Street spent most of the 1950s, 1960s and 1970s cruising the Caribbean —before the guidebooks, before the mooring balls, before bareboating charter companies, and before the 5-star resorts. 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.
“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 do you think secretaries and editors are for?’” (Andy Schell, Sail, Aug. 2017)
Street’s Cruising Guides to the Caribbean
His Cruising Guide to the Lesser Antilles, published in 1964, 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 his 46-foot engineless yawl, Iolaire, built in 1905. He has made 12 transatlantic crossings, all of which were hand steered with no autopilot.
In addition he wrote –
- Street’s Cruising Guide to the Eastern Caribbean: Puerto Rice, the Spanish, U.S. and British Virgin Islands
- 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
The Birth of Bareboating in the Caribbean
“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 said with a wry smile.’” (Andy Schell, Sail, Aug. 2017)
CSY was located in Maya Cove on the south coast of Tortola in the BVI. By 1969 it had 9 boats located there and owner Van Ost ran the business from his dental office in Ft. Lee, N.J. between filling his patients’ teeth. He was followed in 1970 by Charlie Carry and The Moorings.
He was a frequent Scuttlebutt commentator, often sharing stories from his early years growing up in Manhasset Bay on Long Island. He had little tolerance for boats being abandoned at sea, with inadequate bilge pumps as a reoccurring topic. Following a recent death by seasickness, he was quick to share his remedy.
His life couldn’t have been any bigger or fuller. From growing up getting schooled in sailing by the likes of Jack Sutphen, Arthur Knapp, and his sisters, to serving on submarines during the Korean war, and quitting a NYC banking career early on to go sailing in the Caribbean. His most recent passion has been racing his Dragon in Glandore, with a predominantly teenage crew that he trained.
For those who would like to know more about the life and adventures of Don Street, go to his website here.