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Last year I flew that route about 25 times. With carry-on, I could make an InterCaribbean flight with about 45-60 minutes of layover but that assumed I was sitting up front. They do not even open the gate agent desk until 30 minutes before the flight.
If you are checking bags, you need most of that 2 hours because you have to exit security, find your bags and check in with bags 60 minutes before the flight. 90 minutes might be doable but it would be tight.
I think they are pretty reliable. Sometimes they cancel the mid-afternoon flight and make everyone fly on the 6pm flight. I suspect that is all about filling planes even though they don't say that.
Enjoy!
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