Always carry-on. Besides the cost savings (like just the return flight baggage fee pays for, oh, Club MoBay), I like saving the time when I leave Jamaica. If I don't have a bag to check I get to go to the kiosk to check in and in two minutes I'm on my way to security. Checking a bag means I have to wait in those awful lines for a person to check me in...no thanks, I'll spend that hour in Jamaica doing fun stuff!

As a matter of fact, the flight out was very full so they asked for volunteers to check bags and we did - right at the gate, no waiting, no fee. That I'll do if the opportunity arises.

This last trip I had a wheeled carryon and a backpack and still brought too many clothes (on a 10 day trip).