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Where should I vacation Memorial Day weekend?

I'm taking a couple of extra days, so it would be Saturday-Wednesday. Been in NY a bunch lately, so not there. My favorite Caribbean island doesn't have any rooms at the place I love. Looking to chill, meet and talk with interesting people, have some decent food / wine. I would prefer to be in shorts / blue jeans and not have to get too foofy. I have a bad habit of going to my favorite places repeatedly, so no Vieques, Buenos Aires, London, Amsterdam, Paris, Toronto, or Montreal. Europe or South America may be too far for a five day trip, anyway. Suggestions? I'm in the southeastern US.

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