Arriving to a Caribbean Island by plane - leaving by private boat. What about the Visas??

Hello together!

We want to join a boat in our trip through the Caribbean, and continue traveling from island to island by boat. We are wondering about the entry requirements of the most lands: if you enter by plane, they want to see a plane ticket out. It's like this at least in Cuba, Puerto Rico and the other USA islands, and British Virgin Islands and the other British islands. How to continue by boat then?? Can you show at the border an invitation of a captain to join his boat?

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You didn't mention your nationality, but as a US citizen and frequent delivery sailor I've always flown in, gone through that country's Immigration.  I've been asked boat's name and contact number for the captain but that's about it.  I've then cleared out on the boats crew manifest.  Never any problems. 

Hi i'm in the exumas bahamas and i'm looking for crew 

i'm going to jamaica and then panama 

would you be interested?

cheers

A route I've sailed before!

Depending on your terms, I would be very interested. 

Hi I'm in Jamaica now would like to go by the weekend to Panama
We share expenses
The boat is a morgan 41out island i have already sailed a 1000 milles with it since Florida.

In all cases that I've come across, a letter; formal or informal, from the Captain of the boat is sufficient.  Most of the time, a verbal statement is enough, but sometimes crew have been asked for some documentation.

There are a number of templates on the web, but I normally write something like:-

To whom it may concern,

<Crew member> (<passport #>, <d.o.b>) will be arriving on dd/mm/yyyy aboard flight <flight #> from <someplace> and joining the crew of <Yacht name>

<Yacht name> is currently lying <harbour> and will be departing <expected departure date> on a private cruise of <some islands>.

regards

Captain

<Yacht>

<Some more yacht details ( Flag, home port, reg number etc.)

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