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We have always cruised in March or the first week of April and the weather has always been great.  Jamaica and Grand Cayman were really warm the couple times we've been there.  I've never been to Key West so I can't say anything about the weather there.  We've always packed shorts, t-shirts, tanks, your basic summer clothes and those have always been fine.  I've never had to use pants on any cruise I've been on (during the day) and I do always take a light sweater but have never had to use it. For the evenings on the ship I always have a skirt or capri pants on and my husband wears pants and a shirt for dinner then we go to the shows like that and are always comfortable.  The ship can sometimes be cool but it's never been bad or uncomfortable for us.