Latest Updated Guides

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Donald Street's DVDs
With Don's Streets half a century of experience this book gives you the benefit of his practical know how at sea
Seawise is a collection of ideas and uses for the equipment available to the yachtsman in the 1970s. It has been updated in the light of the new equipment available today and the experience I have gained in my life time. Now in 2004, up-dated and back in print.
A history of the Caribbean and a sailing guide
"Nostalgia, humour and fact"
The Guide that opened the Eastern Caribbean to the cruising yachtsmanb and made bare boat chartering possible.
Detailed Sailors cruising guide to the Virgins and Puerto Rico
"In the beginning was the word and the word came from Street.... Since 1964 all other guide authors have followed in Street's and Iolaire's wake, avoiding the rocks and shoals Street and Iolaire discovered" —Patience Wales, former Editor Sail magazine.
Street's Guides are for Real Sailors. The only cruising guide with detailed inter island sailing directions
If you are looking to get away from it all then this is the guide for you - find quiet and even deserted anchorages in the most beautiful sailing area of the world.
The Only guide to cover Martinique to Trinidad including Tobago and Barbados in one volume
As Dick Johnson, Editor, Yachting World said: "To find a quiet anchorage buy the other guides and circle in red all the anchorages Street describes that are not described in the other guides."
The Venezuelan guide for sailors wishing to explore along the northern coast of Venezuela and the ABC islands.
This guide is out of print. But rocks don't move, so the navigational information is still as valid today as it was when the guide was written in 1989.
Work is in hand to get this guide updated in the hope to have it back in print by next season.
Guide to the Atlantic islands, Transatlantic Crossings, Getting to and leaving the Caribbean from the east coast of the U.S. and an Introduction to the Caribbean
Yes Iolaire is for sale A spectacular deal for the right person. No boat has ever been offered for sale on such favourable and unique conditions - the reason is that I have owned her for 48 years. As each year
Despite the fact that she is 104 years old she is in as good shape as boats that are only 4 or 5 years old.She needs a new home with someone who will take good care of her, sail her and has enough money to keep her in good shape.
Know how from an experienced ocean sailor of half a century
Ocean Sailing Yacht Volumes 1 and 2 is being updated having been first published in the mid1970s, there is a tremendous amount of information on boats and equipment, gear and rigging tricks of the trade.


All my life I have been a frustrated yacht designer. I started sailing late - at age 12. But I have been around boats since I first knew how to walk. I learned how to row probably around age 6. Once I started sailing, I sailed intensively. By the age of 14 I was interested in yacht design and begged, borrowed (and possibly stole), and bought or persuaded my parents to buy, everything I could find on yacht design.
Old friend Greg Jones is in the process of writing a bioography of L. Francis Herreshoff. Herreshoff evidently saved every piece of paper that crossed his desk.
Greg found two letters that I had written to Herreshoff in about l945 or 46, when I would have been 15 or 16 years old.
Herreshoff answered the letter encouraging me on my idea to become a yacht designer, and encouraged me.
Greg also found a letter from my mother asking Herreshoff not to encourage me, no money in yacht design, I should go to the canyons of New York, make money and spend it on yachts.
I come from a long line of sailors on my mothers side. But, all had gone to the canyons of New York making money and then spent their money on yachts. From an early age I was beaten over the head being told, "You go to the canyons of New York, make money and then you can spend it on yachts. You can't make money in the yachting business."
However, I ended up sailing for a career. Although I am not a formally trained yacht designer, or been trained as a marine engineer, I have learned enough by reading extensively and sailing extensively; discussing yacht design with trained yacht designers and engineers, to become somewhat of a yacht designer.
When I first bought Iolaire, she had been noted as a fast boat but her weather helm was so bad that if you sailed on her for more than a month you would look like a Orang-utan. The weather helm having pulled your arms all the way down to your knees. I have succeeded in redesigning Iolaire's rig to the rig she has today which so well balanced, that my wife Trich, who weighs 100 lbs. Can handle her in all but extreme conditions. We changed her from a fths double head sail cutter, to a mast head, double head sail yawl
Similarly, on Li'l Iolaire which as a sloop had a rather strong weather helm, now is a beautifully balanced yawl.
With extensive sailing experience including almost 40 North-South trips between the Caribbean and the east coast of the States and Canada, I became a yachting writer, writing my first article for Yachting in September 1964. There followed almost 200 yachting articles, a series of Caribbean guides, a Transatlantic Crossing Guide plus Ocean Sailing Yacht volumes 1 and 2, and finally Seawise which is a collection of articles which I wrote between 1964 and 1977, when Seawise first went to print.
This book was well received but has long since been out of print - as happened to my guides and Ocean Sailing Yacht. However, because of electronic printing and being a member of The Authors Guild, I discover I can get all my books back in print. Also I discover that with a prologue and epilogue I can bring them up to date to reflect the changes since the books were originally published.
In the Prologue of Seawise, I have tried to bring what I wrote back in the 1960s and 1970s up to date, in the light of new equipment available to the yachtsman of today, and in the light of the further experience I have gained in the last 23/​24 years.
As to how I arrived in the Caribbean, how I avoided the canyons of New York and how I became a yachting writer - read on.....

People are always asking me when did I get to the Caribbean and how did I end up in the writing business.
I come from a long line of sailors, on my mothers side. My great grandfather raced ice boats and sand baggers in Barnegat Bay. As a young Irish American he was distinctive in that he not only owned a sand bagger, but he actually raced on it. They didn't let him touch the tiller but he was out there, sailing, drinking and getting into the fights afterwards. He died young, and his father, my grandfathers father set my grandfather to work at a very young age. As he said, he had a spoiled ne'er do well son, he was going to keep his grandson on the straight and narrow!! My grandfather started in the bank at a young age. I don't think he even went to university, but became a successful banker, and a very successful sailor in the great South Bay. He produced 11 off spring - all of whom were sailors including my mother. My father who did not sail when he met my mother, set me sailing in Port Washington, in Manhasset Bay Yacht Club. I took to it like a duck to water.
My father was an avid tennis player, tried to teach me tennis, but I went out sailing and that was the end of tennis. At times people said, well tennis loss and sailings gain - no way! My switching from tennis to sailing was tennis's gain. I was most inept at tennis.
Once in university with two friends we formed a winning sailing team. However, the Korean war came along and the fox holes in the Puscan perimeter did not look very healthy, so I volunteered to the navy.
The Navy in it's wonderful ability to put square pegs in round holes, decided that I had tremendous mechanical ability. I should go to a 52 week diesel engine maintenance school. I discovered that the only way I could get out of diesel engine school was to volunteer for submarines.
I ended up in subs where they decided I was too dumb to be an enlisted man so they had to make an officer out of me. They sent me off to Notre Dame on the R.O.T.C. programme. That did not work out, as I ended up head to head with the commanding officer who insisted I could not wear my submarine dolphins on an R.O.T.C. uniform, yet I knew I was legally allowed to do so. Then he insisted I went on freshman cruise despite the fact that my record showed because of my sea time on the subs., I was exempt from freshman cruise. One thing led to another and finally he stated, "Well, if you don't like it you can resign." I said, "What? Resign and go back to the navy as an enlisted man?" He said, "No. You resign and you are a civilian." I grabbed a piece of paper off his desk and wrote out my resignation. He said, "you can't do that". "But you just said I could. Goodbye." End of Naval career and back to Catholic University Washington DC in 1954 where I majored in American History.
I landed a job as paid hand on Huey Long's Ondine, a beautiful 53 foot Abeking and Rasmussen Yawl. I was hired as paid hand and a month later they fired the skipper. I ended up as skipper, with no increase in wages! An interesting couple of years followed included racing in Europe. Huey was not that much of a sailor, but he located some excellent sailors from whom I learned a tremendous amount. Arthur Knapp, then king pin of the international class (called IOD's in Bermuda and Europe); Sven Hansen - who subsequently won the Fastnet and the Bermuda Races back to back on his 48-ft. yawl Anitra; Colin Ratsey of Ratsey & Lapthorne; Charlie "Butch" Ulmer, father of the present Charlie "Butch" Ulmer. Charlie had made sails for my grandfather's boat Molly when he was a young man while working at Ratsey & Lapthorne, and took excellent care of me for many years. Knut Reimers, the famous Swedish designer sailed with us on Ondine in 1955.
Our parting of the ways came just before the Fastnet Race when I told Huey exactly what to do with his 53-ft. black yawl and 54-ft. aluminium mast! I stalked off the boat and made a Pier Head jump onto Lloyds' Yacht Club boat Lutine, a 57 foot. J Laurent Giles designed yawl built by Camper Nicholson in 1953. Sailing on Lutine with Jack Giles was rather interesting as Giles spent the entire race telling us everything that was wrong with Lutine. Yet I thought then, and still feel today, that Lutine was the finest boat he ever designed. Despite the fact that Giles was a superb designer he always rigged his Mizzen mast backwards. (See Ocean Sailing Yacht Volume 1, pages 124-125 for a discussion on this.)
The pier head jump was such that half way down the Solent, Sandy Harworth, Commodore of Lloyds Yacht Club, Rear Commodore of the R.O.R.C., and leading marine underwriter, turned to me and said, "Young man, who the hell are you and where did you come from?"
They evidently liked my sailing ability, as I sailed the rest of the season on her, bounced around Europe for about nine months, and sailed back across the Atlantic (the first of my eleven trips) on Arabella, a 46 foot ketch, as cook and apprentice navigator.
The summer of 1956 I spent sailing delivering boats, helping friends out in boat yards doing odds and ends. Everyone was after me to take a real "job". I asked "Why?" I had money in the bank, did not owe anything on my car, I was making more than I was spending. But, the pressures mounted and I ended up in the job market. I landed a job, at Frank B. Hall & Partners, big ship Marine Insurance brokers on John Street—in the canyons of New York.
One of the conditions on taking the job was that I had to shave off my beautiful (then red) beard. The weekend before I was to start, we were racing frostbite dinghies in Larchmount and Dick Ronan said, "my God, Don you are the only person in New York who is using chap stick on your entire face." I thought about it, and decided I didn't like cold weather.
At the age of 55, after three cases of ulcers and two minor heart attacks, fighting the canyons of New York and commuting my father had to retire— living in that atmosphere my mother had two minor cases of ulcers—At the age of 72 I haven't had an ulcer or a heart attack, I give them!!
You can't change the weather, but you can fly to where the weather is good. A friend had just come back from the Virgin Islands and told of the wonderful climate, the good sailing and an evolving economy in the Virgin Islands.
So, for $45.00 I bought myself a ticket on the "Vomit Comet" a Pan-American DC6—so called because in those days the propeller planes couldn't fly over the storms they flew through them! They didn't really take off from Idlewild (now Kennedy) they just flew down the runway, the runway ended, they pulled up the wheels and staggered off across Jamaica Bay. The rate of climb predicated by how fast the fuel was used up. When they hit an air pocket the plane would drop around 500 feet, the "barf" bags would come out, and the Puerto Ricans would have their rosary beads going round like a bicycle chain.
I landed in San Juan in the wee hours of the morning—and picked up for $10, the Carib Air flight to St. Croix. A few days later I ended up in St. Thomas, and landed a job as a land surveyor.
People ask how did I do that, having graduated with a History Major. On Friday I borrowed a book on basic surveying. Monday and Tuesday were bank holidays. By Wednesday morning I convinced them I was a surveyor—in the land of the blind the one eyed are king.
Not too long after I arrived in St. Thomas I met the late Captain Bob Crytzer who owned three boats. Little Electra, a sister ship to the 44 foot academy yawls, big Electra a 56 foot Camper Nicholson ketch (Owen Aisher's original Yeoman) and Iolaire, 45 foot engineless cutter—owned for many years by Bobby Somerset. Iolaire had been across the Atlantic five times and was presently engineless (that is a story you can read in Caribbean Capers). Glenda Crytzer was trying to convince her husband that he really didn't need three boats. Bob took a liking to me, one thing led to another and I purchased Iolaire for $3,000 down, $1,000 a year for four years, with no interest and no repossession clause!
I slowly drifted into the charter business. Then the exploration business and then the writing business. All of that will described in great detail in Iolaire and I - a history of Iolaire, her previous owners many of whom were very famous, and my sailing career with Iolaire both adventures and misadventures over the last 48 years. A book that is presently on a back burner and hope to get back to after updating all my original books.
Those who like my writing can thank John Steinbeck, John Fernly and Burt Cheveleaux.
My first charter after rebuilding Iolaire when she had been wrecked in Lindberg Bay was John Fernly (He had been casting director for Rogers & Hammerstein for many years) and his good friend Burt Cheveleaux who had just written Something Funny happened on the Way to the Forum (one of the most amusing characters I have ever met in my life). We stopped at Caneel Bay to have cocktails, then dinner with John Steinbeck—very good friends of John Fernly.
A week or so later on the charter we came back and had another evening with cocktails and dinner. The subject came up on writing and talent. It was kicked around for quite a long time, until finally Steinbeck said, "Hell forget all the B.S. on talent, becoming a good writer depends on your ability to put your ass on a hard wooden chair and look at the G.D. typewriter for six hours a day, seven days a week and pound something out. Eventually an editor will accept your work."
Later that evening he turned to me and said, "Kid you tell a good story. Why don't you try writing?" To which I replied, "But Mr. Steinbeck," "Never mind Mr. Steinbeck, call me John," "John, I can't spell or punctuate." To which Mr. Steinbeck replied, "What the hell do you think secretaries and editors are for? Try writing. Go get me a drink." I went to the bar to get Steinbeck a drink and had to report that despite it being only 10.00 p.m., the bar was closed. Steinbeck said, "My God, this is a great place for newly weds and nearly deads. I don't know what you characters are doing, but I'm going back to my room to wrap myself around my bottle of scotch. Good night." That started my writing career.
D. M. Street Jr. Sailing Experience of half a century

D. M. Street Jr., a lifetime sailor, has spent forty five years cruising, charting and writing about the Caribbean. forty of those years were spent in his 46ft. engineless yawl, Iolaire, built in 1905. He has spent the last four years on his 28-ft. engineless yawl Li'l Iolaire, gathering information for his guides in the winter and cruising European waters on Iolaire in the summer.
INSURANCE: D. M. Street Jr., has been in the marine insurance business for 40 years, 36 on his own placing insurance with Lloyds of London. He covers yachts of all ages sailing in the far corners of the world. For information and quote, e-mail: streetiolaire@​

Profile in Brief

Birth Name: Donald M. Street Jr.
Home: Wherever the anchor is down.
Last Sailing Book Read: The Smeetons "Once Is Enough", a perfect illustration of my views in avoiding certain areas.
Sailing Accomplishment: For half a century I've sailed Iolaire', and engineless yawl built in 1905.
Favourite Crew Position: Rock, Tide & Wind Pilot - Aboard Matador, War Baby, Windigo, Flying Scotsman, Shamrock V, Stormy Weather, and many other boats.
Favourite Crusing Destination: Los Rogues - see the picture on the home page of Iolaire at anchore to see why.
Most Dangerous Sailing Experience: Rounding Cape Finisterre
Most Humorous Sailing Experience: Coming back from a day charter to Caneel Bay, my Charter party said to me - "Gee you had better start the engine Skipper, or we won't get back in time for dinner."
The background for the above story is, In the days when Iolaire had no engine but a God awful noisy Stewart Turner Generator. We had sailed up to Caneel Bay, had lunch and were on our way back. There wasn't too much wind when our charter party made this comment. he didn't realise Iolaire did not actually have an engine. I went down below and started up the Stewart Turner generator, that made one hell of a lot of noise, then went back up on deck. I said, "You know these British boats with their little tiny engines we had better motor-sail." I carefully trimmed the sails, and we sailed back to St. Thomas. As we came sailing up toward Yacht Haven, I said, "Let's be sporting and sail along side the dock." and went below and turned off the generator. We sailed her alongside the dock and everyone got off happily. Of course all the other charter skippers knew I had no engine, but no one let the cat out of the bag. They all piled on board when the charter party left and demanded beer in payment for keeping their mouths shut!
They also wanted to know how I had convinced people I had a working engine on Iolaire.