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Never been on one myself.
But know people who have. And winter months, though a little expensive, they say is best. Here's why: no kids.
I've heard several funny (only after the fact) stories about parents not controlling their kids on cruise ships. So you may want to factor in which trip or cruise lines will have less kids. I suppose you'll have other things to attend to...
Oh, yeah. My vote, which counts for absolutely squat, is for the San Juan departure. My parents went on a Carribean cruise, and their two favorite stops were St. Marteen and St. John's/Antigua.
Have fun.
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