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.

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