Just for the next 10-15 years in FL and the Bahamas you might want to look at a Gemini catamaran. Lots of room, very shallow draft (1'6" boards up), and an excellent owners support group on Yahoo. There's a 20 yo model for sale right now in St. Augustine for about 40k, and usually a bunch of newer ones in your price range. They have done blue-water cruising, but not everyone agrees that they are fit for it. Still, 15 years is a long time. The shallow draft will expand your cruising grounds, and, while few people in the anchorage will be saying "Look at that gorgeous boat" as you sail in, neither will they be saying, "Look at that gorgeous boat that just went aground."
Just my opinion. I am mono/multi neutral.