Re: Communications in the Caribean (cell phone)
Even if your phone is international capable, I've found the roaming reliability to be very poor. You might be able to get a local prepaid SIM card in each country for your phone.
The idea of rental one locally is much more reliable.
Even better are the skype, oovoo, viber, etc options for wifi calling. Amazingly cool when you find wifi access.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.