Nassau, Bahamas
I was crazy enough to want to attend both NANOG, in Toronto, and Joint Techs, in Minneapolis, during the northern winter of 2007. There was a week's gap between the two but I wasn't crazy enough to want to stay "enjoying" winter in North America so I fled to the warmth of the Bahamas. I stayed at the Hilton in Nassau and just wandered around, watched the cruise ship tourists rush around, and enjoyed the warmth. I wasn't tempted to go across to the casinos on Paradise Island.