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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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It is much better to send too much information than too little. If the broker or underwriter needs information not in the original request it delays everything a couple of days while e mails fly back and forth.


  • Name
  • nationality
  • age
  • occupation resume of sailing experience including description of boats owned.
  • Marine insurance claims record.
  • Description of boat.

If a standard production model:

  • date of build
  • designer
  • engine make,hp and age.
  • years of ownership of boat to be insured

If a one off:

  • designer
  • builder
  • date launched
  • dimensions
  • rig
  • engine, make, hp, age

All boats If the boat is more than three years old Copy of latest survey with all surveyors' ESSENTIAL recommendations complied with or stating the essential recommendations will be complied with before insurance attaches. If no survey is available will they be willing to quote subject to sight of satisfactory survey with all essential recommendations complied with before insurance attaches.

This is important as you do not want to go thru the expense of hauling and paying for a survey only to discover they are unwilling to quote because of valuation, age, or some other factor. Value of boat, basically what you paid for the boat, plus money spent on capital improvements. The insured value must be close to the approximate re sale value of the boat.

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Prior to the early 90s there was little difficulty organizing insurance with companies in the states, UK or Europe to cover boats in the eastern Caribbean. However, starting in the 90 s yachting in the Caribbean expanded on a steep curve. Since about 2010 yachting has expanded exponentially causing huge financial losses whenever a hurricane hit a yachting center.


Starting in 84 with the late season early November wrong way traveling hurricane Klaus which caught the St Thomas Chart Boat show, 17 hurricanes have hit the islands of the eastern Caribbean. This works out to one hurricane every other year. In most cases, the hurricane hit a major yachting center causing catastrophic damage.


As a result, Panteneas and virtually all Lloyds yacht underwriting syndicates have decided that theie reserves will earn a better return if they cease insuring yachts in the eastern Caribbean

With the two major players pulling out, it has become difficult to insure boats based in or cruising in the eastern Caribbean.


In the states when trying to obtain coverage you may find yourself dealing with both brokers and agents for large insurance companies. Brokers obtain quote from insurance companies. Some agents for some of the big companies ,to use the insurance term, to hold a pen, ie they can set a rate and insure a boat without going to head office. As long as they have a good win loss record, head office leaves them alone. Thus, head office may tell agents not to insure yachts in the eastern Caribbean while an individual agent may continue to do so.


In the Caribbean you are usually dealing with either a broker who tries to find a company to insure your yacht, or a local insurance company who will insure your yacht. Often sailors will say they are insured with LLoyds, thinking they are insured with a Lloyds yacht underwriting syndicate .but they are not. The local insurance company insures the yacht paying claims out of their reserve fund they have built up over the years. The local underwriting company's reserve fund is backed by an excessive loss policy usually in Lloyds, so they tell the customer they are insured with Lloyds

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Many sailors go uninsured saying they would rather spend the money installing good equipement, checking it replacing when necessary thus avoiding breakdowns and replacement

Some sailors have done this and spent a life time sailing and never had any problems requirng a large outlay of cash to solve damage or gear failure. The Pardeys are a prime example, twice around the world in two different boats, both engineless yet no problems.They were skillful but also lucky, read the below five stories.

November 8 1984 Charlotte Amalie harbor was crowded with yachts assembling for the VI Charter Boat Show.

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