Originally Posted by
PDXPremier
Yeah, we were going to cab to and from the airport. Yes, we are one ticket but since the layover is over 4 hours, I figured they would only check the bag as far as EYW when we check-in at MIA....even if we check it through, I would imagine it would still find it's way to baggage claim in EYW since I doubt they have much "connecting" traffic there

Oh. Well. Then the first question to ask would have been: "How long a connection will AA allow for a check-through, and is EYW an exception to that?"
I
think the answer is 12 hours,
as stated here, as long as it's not overnight. But as noted above I've been wrong before.