Does anyone understand other Caribbeans dialects?

Can Jamaicans understand each other and other Caribbean islands? I remember seeing two Jamaicans from different areas not understand each other. Can Jamaicans understand Bajans and Trinis? I find it easy to understand Trinis, but I can't understand Bajans. They sound like they're speaking gibberish. I also have trouble understanding Jamaicans from the East side of Jamaica. Some of them sound like they're talking gibberish as well. I was talking to this Jamaican, and he would always put a phrase in the middle of his sentence that throws me off completely. I know Jamaicans love using phrases or "sayings" in their sentences, but some of you guys do it on purpose even when you don't need to.