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Hi. I tend to favor South Florida (Ft. Lauderdale and on down) because it's warmer in the winter. That said, last week was cold for all of us.
As one commentator noted, we do have people in the water year around, although many of us would not consider going into the water before or after August. (Yes, we are that bad!)
I love the idea of a cruise. When my son first came home at two, we were off and away very shortly and have cruised a couple of times a year since then. I find it a wonderful father/son getaway. Most of the cruiselines have kids' activities (even for very young ones), but you would want to check this out in advance. Disney cruiselines, followed, in my opinion by Carnival and then RCL, have fairly good kids' programs, if you want some time on your own.
Make sure you check, re-check and ultimately quadruple-check what papers your child will need to visit the various countries and to get back in to the US.
We all look forward to having your family visit us for a while.
Bob
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