Obits

Eight Bells: Donald Street, Jr.

Don Street, Jr.

Don Street, Jr. opened up the Caribbean for cruising sailors, bareboating, and the joy of sailing for generations of newbies.

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)

Don Street, Jr. on Iolaire

Iolaire, built in 1905, and bought by Don Street 50 years later for $7000 on an annual installment plan from the owner, was home to Street for decades as he roamed the Caribbean.

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

Don Street, Jr. at the helm of Iolaire

Street at the helm of Iolaire, which he sailed across the Atlantic five times. It was a floating wreck, with a deck pocked marked with dutchmen and repairs nearly everywhere, but she was home for Don.

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.

Don Street, Jr. in the 1960s

This image of Don taken in the 1960s of Don as a young man, appeared on the cover of a number of his sailing guides.

“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. 

Don Street, Jr. in his Dragon off the coast of Ireland

In his Dragon off the coast of Ireland, Don still fortified himself with a “greenie,” something that he never changed from his early days in the Caribbean.

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.

Don Street, Jr. at 90 racing

Don at 90 still enjoyed racing the young hotshots.

For those who would like to know more about the life and adventures of Don Street, go to his website here.