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DON'S LOG: stories, experience and advice

Insurance and the beginning of yachting in the Caribbean

INSURANCE and the beginning of yachting in the Caribbean, and its expansion to its present state, why it is now so difficult to obtain insurance coverage in the Caribbean, Don Street’s insurance experience, and advise as to how to obtain insurance coverage.

I arrived in St Thomas in 1956. I bought the engineless 46’ cutter Iolaire, built 1905. In Iolaire and then L’ll Iolaire, and other boats, for the next 63 years I cruised, raced, chartered ,explored, charted and wrote about the Caribbean.

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Underwriters are not properly evaluating yachting risks in the eastern Caribbean

My great grandfather Col.Hugh McQueen Street was in the insurance business in Vicksburg Mississippi. He sent his son Charles Richard Street at age about 18 north to Chicago to learn the insurance business. This he did and became one of the leaders in the industry. He was famous for the fact that he could smoke a cigar, have a conversation on the phone and with the man sitting at his desk all at the same time.

He was also famous for saying”there area few brilliant people in business who are from the south” stressing the word From!

Digging thru his papers I came across an letter that was sent out to all his agents. “all risks submitted do not have to be prime risks. Describe the proposed insured and the risks. I will evaluate and come up with a premium that the insured can afford and we on the long term basis can make a profit”.

Unfortunately at the present time this does not appear to be the situation in the yacht insurance industry in the Caribbean.

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Yachting in the Caribbean began as a trickle in the 50s, which was the beginning of the charter industry in ST Thomas and Antigua. It got rolling in the 60s, accelerated in the 70s, sky rocketed it in the 90, and has undergone an exponential yearly growth in the 21st century.

In the early years many of the boats were uninsured. Insured boats, some insured in the state, some with Lloyd's. Almost all English boats were insured in Lloyd's.

There was no one in the eastern Caribbean who specialize in marine insurance.

I arrived in the Caribbean in St Thomas the end of November 1956, and bought in March 1957, Iolaire a 46' engineless sloop, later converted to a yawl, built in England 1905.

After working at various jobs I ended up in the charter business skippering Iolaire.

While I was teaching sailing at City Island YC the summer of 1961 I felt that I might not want to spend the rest of my life as a charter skipper so I took a three night a week course in insurance brokerage that would lead to taking an exam for NY state insurance broker license.

I completed the course, passed the exam but did not stay for the NY State Insurance brokers exam. Rather I sailed Iolaire south to St Thomas.

I discovered in my absence that a newcomer had set up an insurance brokerage office, basically general insurance but also marine. I was quickly hired and combined chartering Iolaire and selling insurance, marine , but also house car and motor cycle!!!!

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When I arrived in St Thomas yachting had just barely begun in St. Thomas and Antigua. In St Thomas there were on more than a dozen and a half boat in the Charlotte Amalie anchorage. The industry was supported by the fact that the USVI court was a federal court. A divorce granted in a VI court could not be contested. Divorces could only be granted to VI residents. Six weeks and you became VI resident. Hotels catered to gals establishing residence, yachts entertained bored potential divorcees. Young unattached males had a field day.

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Hitches, knots, line, chafing gear, cleats on docks, ring bolts, chain, shackles, swivels anchors vs sand screws

When securing lines it is not only a case of securing but also a case of being able to unsecure and re adjust the line.

When securing to a sampson post, bollard, or a winch, Do NOT use a clove hitch. Once a clove hitch is heavily loaded the only way it can be unsecured is with a good sharp knife.

Use a tow boat hitch, to the Americans, lightermans hitch to the English, as this hitch can be unloaded under heavy strain and line veered.

Lines that are on heavy load may have to be moved. Learn to reliably tie a line to the loaded line with a rolling hitch so that the load can be taken on the line secured by a rolling hitch and the loaded line moved to a better tie off point

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Tropical Hurricanes: Don's Experience

Chart of eastern Carribbean
The Eastern Carribbean. 

Donald M Street, who arrived in St Thomas in the US Virgin Islands in November 1956, is the compiler of the Imray Iolaire charts which cover all of the eastern Caribbean east of Aruba, and is author of guides covering the same area. Over the past 70 years he has built up a tremendous knowledge of how hurricanes affect the yachting industry in the eastern Caribbean




Don Street's first experience with hurricanes was the 1938 hurricane that cleaned out the yachting fleet of Manhasset Bay(where street grew up and learned to sail) by putting ashore or sinking 400 boats. Further east in the Watch Hill, Westerly RI area, it killed 485 people and caused in modern dollars 1.4 billion in losses. It wasone of the most destructive and expensive Atlantic hurricane of all times until Sandy2012 tore New York city and suburbs  apart
Sandy did  more  damage so was  more expensive but  the loss of  life was  lest than 10 % of the  loss of  life  in the  38 hurricane.


Then the 44 hurricane , which NOAA refers to as "the great storm" hurricane force winds in a 600 mile circle sinking a US navy destroyer, a light ship, two coast guard cutter and ? cargo ships carrying supples to Europe. Well more than 300 seaman  must have lost there lives as 276 were lost  when the  destroyer sank. Thus in loss of  life these two hurricanes were the most destructive atlantic hurricane in  history.


Damage  ashore  was not that bad It severely damaged but did not clean out the Manhasst Bay yachting fleet. Snipe number 3 owned by Don Street and his three older sisters survived, but damaged. Street at age 14 filed his firm marine insurance claim as a result of hurricane damage.


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Tropical hurricanes start as a low pressure wave in the region of the Cape Verde islands. Some lows pick up a circular motion and are almost immediately noted by NOAA satellite and given a name. They are then carefully tracked by NOAA/hurricanes with the positions given every six hours.


Tropical depression , have winds to 34 kts/39mph/18mps and a bit more .


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After being caught in 1984 on the north side of St Martins by late season , mid november hurricane Klaus and surviving using six of Iolalire's seven anchors,(click here for full story) I decided that I had to do some research. Klaus was the first hurricane anyone could remember that headed NE in the low latitudes.


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Hurricane Whole (6.39 MB) 

Article from Hands On Sailor - Hurricane Whole


click the above link to down load the file tropical hurricane, their tracks the antilles, their strength and internal tornadoes

BEFORE THE HURRICANE (Click Image to Enlarge)


AFTER THE HURRICANE (Click Image to Enlarge)



2017's hurricanes devastated boats both in and out of the water. If your boat is in the Caribbean, Don Street advises on how you can keep it safe and continue to sail during the hurricane season
An area from west of St Barts to the east coast of Puerto Rico is often called Hurricane Alley, because the islands in the area have over the last 35 years frequently suffered either a direct hit or major damage by a hurricane that has passed close by.

With two exceptions, none of the yard managers have laid up boats during hurricane season in such a fashion that they would stand a very good chance of surviving a hurricane.


The yard attached to Marina Puerto Del Rey had 237 boats properly laid up: tied down, well supported by screw jacks, masts out, no total losses: just three per cent suffered major damage during 2017.


In St Martin, Sir Bobby Velasco says: "I lay up my boats the way my daddy taught me: wooden cradles, everything tied to together with cross spalls, well nailed together and masts out". Boats in Bobby's marina survived undamaged except for sand blast damage from hurricane-blown sand. Elsewhere in St Martin, where boats were hauled ashore there was massive destruction.


In marinas in hurricane alley in 2017, outcomes varied from massive destruction, to many boats sunk, to no sinking but major damage, except Marina Puerto Del Rey. Puerto del Rey with its 12ft-high 1,000ft-long breakwater was specifically built so that boats would survive a direct hurricane hit to the marina. The marina has a total capacity of 950 boats, of which 552 were in the water. Just 4% suffered major damage, 2% were total losses.

As a resut the marina became very popular and  filled almost to full compasity.In 2019when Dorina approached therewere only 45 berths aailable to boats wishing  to shelter  from  Dorian.


In the islands to the south of Hurricane Alley – Antigua, St Lucia and Grenada, where large numbers of boats lay up ashore for the hurricane season – the marina managers claim they have learned their lessons by observing the disasters: Antigua as a result of Hugo, Grenada as a result of Ivan in 2004. They lay up boats properly so that they will survive a hurricane.

Fin-keeled, deep-draft boats have their keels in a pit, boats are in specially built steel cradles or are very well chocked by numerous screw jacks, and boats are tied down with straps to either dead men buried in the sand or sand screws.

But the vast majority of the boats are stored with their masts in. Wind pressures go up with the square of the velocity. When the wind gusts to 180mph the wind pressure is astronomical: 83lb per sq ft. That means that on a 60ft mast with the wind gusting 180 mph, the load exerted 30ft above the deck is 5,450lb. When the wind is fore and aft, or near to it, this load really does not matter. But with that load on the beam, will the boat stay in the cradle?


Every time a hurricane passes through hurricane alley, boats pour into supposed safe havens, such as Ensenada Honda on Culebra, Hurricane Hole St Johns, or inner Benner Bay on St Thomas. In every major hurricane they are disaster areas with a total of well over 100 boats sunk, and a similar number suffering major damage.

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The Ultimate Insurance Policy

Plenty of good anchors and a large capacity hand operated 35gpm diaphragm pump

When cruising the Caribbean all boats should have a minimum of three anchors. The military always desires to go into battle with a mix of weapons. Similarly when cruising the Caribbean you should not rely on one type of anchor. Different bottoms require different anchors.

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Surviving Klaus

In October 1984 one low after another blasted thru Antigua. Iolaire was hauled on the north side of Antigua in Crabbs, no screw jacks, just wooden A frames jammed against the boats, then wedges driven in to hold the boats tight. 


When lows came thru the boats shook so much the wedges would fall out so we finally re drove them and nailed them in place.

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Tracking Hurricanes

After being caught in 1984 on the north side of St Martins by late season , mid november hurricane Klaus and surviving using six of Iolalire’s seven anchors,(click here for full story) I decided that I had to do some research. Klaus was the first hurricane anyone could remember that headed NE in the low latitudes.

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First of all look at the frequency that hurricane have hit the various yachting centers where there are marinas of any size that make leaving a boat there is a possibility. The below figures based on NOAA hurricane tracks since 1975 when yachting in the eastern Caribbean started taking off

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Load on a  60' 1/4 inch halyard secures to a pad eye.

To properly lay up a boat for hurricane season is a job that must be done by owner, his captain, a very trusted friend or be done under the supervision by local surveyor.

Screw jacks or fabricated cradle? Fabricated cradles are seldom designed and built for a specific boat so the arms seldom match up with strong points, like bulkheads or half bulkheads.  Read More 

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pressure plotted against windspeed
If leaving a boat on a hurricane mooring read Street's advise very carefully. Remember wind pressure goes up with the SQUARE of the velocity.

As noted in the introduction, Don Street because of his age 89, and experience with hurricanes on the east coast of the states and Caribbean, he knows more about hurricane tracks as they approach the Caribbean, and their effect on the yachting industry, than any other sailor or yachting author in the world. Read what  Read More 

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A survey of the tracks of all the------- hurricanes since 1851, that have started as lows in the region of the Cape Verdes, as long as they stay below 19N they track westwards seldom altering course more than 5 degrees in 24 hours. The alterations of course is almost universally to the north. If the hurricane, tropical  Read More 

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In my first hard covered Guide (first guide Yachtsman’s Guide to the Virgin islands 1964 was privately printed on a hand powered ereneo to the English mimeograph to Americans 1963) Cruising Guide to the Lesser Antilles l966 (reprinted facsimile editions now available thru iUniverse .com, Amazon and Imray,a wonderful bit of nostalga, the Caribbean in the late 50’s early 60’s) I stated that the best sailing months of the year were may June and July and sometime into August. This is still true today.

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Ever since 1975 when yachting in the Caribbean really took off, for 45 years I have been reading about, and personally being told about the disasters that happened in the so called hurricane holes. Every time a hurricane come thru the islands of the eastern Caribbean boats flock to the so called hurricane holes and disaster  Read More 

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The western part of Hurricane Hurricane Alley Anegada west to Eastern Puerto Rico is well named as since the area really started booming with yachts about 1975 , the area has been hit 8 times, with hurricanes 75, two in 79, 84 Klaus, 89 Hugo, 95 and four times in 2017 by Harvey,Irma, Jose and Maria, in 2019 Dorina which luckily passed thru fast and  did  no major damage.  Plus there  were   another half dozen  tropical storms

Thus ten  hurricanes  in 45 years hence  the name  hurricane  alley..

One would think that everyone would have worked out plans to minimize the damage caused by hurricane, but unfortunately they have not. This is the reason it is difficult to obtain insurance in the eastern Caribbean and especially for boats based in Hurricane Alley. Read More 

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Effects of wind on 50ft monohull with a 60ft mast laying head to wind
Effects of wind on the achorline load of  50' monohull with a 60' mast laying head to wind. Note loads increase drasticallywith larger boats.

This is not a good idea as is illustrated by my loss of L’ll Iolaire in hurricane Ivan in Grenada in 2004. Iike most sailors felt that Grenada that had only been hit by two hurricanes, one in 1856 and in 1955 Grenada was basically south of the hurricane area. Every summer starting in 1996 we laid up L’ll Iolaire on a good heavy mooring, chain to a rope attached to a buoy. From the buoy to L’ll Iolaire two separate lines lead thru two separate chocks to two separate cleat bolted to big backing blocks. Lines were carefully cover with chaffing gear.

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Tropical hurricanes start as a low pressure wave in the region of the Cape Verde islands. Some lows pick up a circular motion and are almost immediately noted by NOAA satellite and given a name. They are then carefully tracked by NOAA/hurricanes with the positions given every six hours.

Tropical depression , have winds  Read More 

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HANDS-ON SAILOR Article "Hurricane Whole"

There is no other yachtsman or yachting author that can match Don Street’s experience with hurricanes ashore and afloat, gained over the last 78 years, Read More 

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