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Discussion Starter #1
I'm heading to the Caribbean in late November 2019 to both get sailing exp and to find a boat to buy. I'm planning on spending 6 months cruising the Caribbean to start and am going to make it a full time thing within the next two years. I'd like to get more experience by crewing as I look for a boat. My 15 years of sailing experience is limited to cruising and racing the US Pacific Northwest.

My question is where in your experienced opinions should I initaly fly into, in the Caribbean, to both find a good number of will found cruising sailboats for sale as well as to find boats looking for crew? I've been looking online for the last few years but I've come to the conclusion that i need to be on the docks somewhere before i start making plans to crew (want to meet people/captains personally) and to be able to look at boats.

Thanks for your input.
 

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St Martin, Grenada, Martinique.

Martinique is better if you are comfortable with French speakers.


Crewing on cruising boats isn't quite normal. If you want to crew in the big race regattas go to Antigua in Sailing Week etc.

As a general thought, I would suggest you totally concentrate of boat buying. And lack of experience is made up for in 1 week on your own boat.
 

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MSL’s “one week” is a bit optimistic imho. We’ve spent 6 years at it so far and still don’t know what the hell we’re doing.
Would avoid the French islands during carnival. Would start in the leewards as the sailing is much easier and due to the higher numbers of charter boats services easier to find. For local knowledge and questions the vhf cruising nets are often quite helpful.
My list of islands is different
Bequia, Dominica, Grenada, French side of st.martin for cruising. For buying you need to decide if you are looking for an ex charter boat, a new charter boat or a cruising boat. For prior cruisers Grenada’s southern bays, Trinidad and Rodney Bay would lead the list. For ex charter BVI would be #1 then anyplace there’s a Moorings.
Boat hopping through the islands is done but usually by 20 somethings. We had a very bad experience with a young polish man so will never offer a ride again. Customs frowns on you just giving a ride. The hitchhiker needs to have hardcore proof he/she has lined up transfer to another cruising boat or has paid for airplane ticket and housing until then or they remain your responsibility. They don’t want indigents left on their island. This makes island hopping difficult as cruising boats usually don’t want that responsibility for someone they don’t know well.
Cruisers are set up to be self sufficient. They only need crew for passage.
 

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Cruisers down in the islands don't need crew and don't want strangers aboard. Most likely boats would be ones coming off charter. Contact the charter companies to see what's for sale. Cruising will mean you have to re fit the boat for live aboard cruising. Try a English speaking island like Antigua or St Martin.
 

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The market in the BVI is quite good if you are looking for an ex-charter boat. The good news is that you don't need to travel away from your computer to look for possible boats as just about everybody uses www.yachtworld.com and you can narrow down your selection quite easily. A "cruising boat" in the Caribbean is somewhat different from the rest of the world; the conditions there are generally benign during the cruising season and anchorages are usually easily reached. All the islands are within a day or at most 2 days of sailing from their neighbors. You don't need an expedition boat and although I hesitate to say it, a catamaran is a pretty good and comfortable platform.

As others have said, you won't find crew positions on cruising boats. You might find a boat willing to take you from A to B on passage, but even that is sometimes difficult to do. Crewing during regattas is easy, just show up at event like the Heineken Regatta in St. Martin or Antigua Sailing Week and you are almost guaranteed to find an open slot somewhere.
 

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In the fall rallies to the Caribbean there are usually a handful of skippers at the arrival point in the BVIs looking for crew to accompany them to the windwards. Most of the offshore crew returns home as soon as possible so there are usually opportunities to hop on with a skipper who wants to make it to a certain island in time to spend Christmas there and/or to meet up with a spouse. Of course, once you get to the windwards your luck will probably run out as far as finding other boats willing to have you as crew - at least until they are ready to head back north in the spring.
 

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There are plenty of boats and not just ex-charter boats on the hard for sale in the Windward Islands. Boats of broken dreams I call them. Folks who planned on retiring to cruising and put a great deal of work, money and time into the dream and found they didn't like it. Most initially try to recoup their investment, which is near impossible, and put a pretty high price on the boat, but as time wears on, depending on their need for the money, they soon realize that they must take what they can get. If you can sneak in before the boat goes completely to hell from sitting too long, you can come out a winner.
As some have suggested, the BVI's are a great place to get an ex-charter boat, but what's left on the market are most probably the dregs of the Irma/Maria rebuilds. St T. might be slightly better, but just as after Katrina when there were thousands of "refurbished" autos being sold all over the US and Caribbean very inexpensively, these boats will probably become maintenance headaches in the long run.
My bet would be on Trinidad. There are two yards there filled with what seem to be deserted 'dreamboats'. Many are very well found and in pretty good shape. One I know of is Explorer in Powerboats yard; give them a call and ask.
As for sailing with cruisers, I think that's been well covered above and most likely undoable. However, if you are vacillating between a mono and a cat, I would suggest you bareboat both before you make that choice. They are world's apart and each certainly has it's good and bad points which you will not fully understand without a couple of weeks traveling aboard. And don't pussyfoot around; go out when it's snotty as hell or you won't really know what you are getting into.
Grenada has some boats, but St Martin would probably be better, though you are once again running into what's left two years after Irma/Maria, in general.
Good luck and we hope to be seeing you sailing down here pretty soon.
 
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There is a nice CSY 37 on Dynamite brokerage in Trinidad. Won't win many races but a comfortable cruising boat for two with 150 galls water.

IMHO Grenada Trinidad and Martinique are the places to look. For example there is a very cheap Amel Sharki up for sale in Martinique it could be a total shed or someones broken dream.

Buy a boat and go sailing cruising is not rocket science. Maybe get some help for a week then most people will be good to go.
 

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Discussion Starter #10
Thanks to all of you for your helpful information and time! I am researching these options for a starting location and am very excited to get going.
 
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