Advice on sim card for caribbean, and USA

Hope someone can help...

I'm trying to find a SIM card for use in my phone whilst cruising around the Caribbean in a weeks time - going to places like Dominica, St. Kitts, Barbados etc.
Also needs to work however in the Bahamas, and also in Puerto Rico and Miami.

I'm considering the 'Red Pocket Unlimited SIM Card' from usasims.com, but it's not clear to me if that card will only work whilst in the US and Puerto Rico, or if it allows me to roam to the Caribbean islands as well.

Flying out on Tuesday 24th, so guess I'll need to go with a company who can deliver to my airport hotel (in Miami Hilton on the night of the 24th before flying to PR on the 25th). Think usasims.com do offer this option.

Any thoughts/advice would be appreciated - mobile phones really aren't my thing, and really confuse me!
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