a winter vacation was in...I wanna say January 2008? 2009?...when I attended my cousin's destination wedding in Mexico, in Playa del Carmen. In addition to enjoying the sun and surf at the all inclusive resort where we were staying, and where the wedding was (on the beach), I got to see "Fifth Avenue" (the tourist trap...umm...shopping district nearby) and the Mayan ruins at Tulum. It was WEIRD getting on a plane in Cleveland in the dead of winter, bundled up in a winter coat and hat and gloves and then arriving in Cancun and stepping off the plane into 70 degree sunshine. And annoying getting used to the warmer weather and then returning to frigid temperatures less than a week later. My body doesn't care for temperature extremes like that in a short period of time <g>.
I was never a huge fan of the summer vacation either, TBH. Too many people, especially children, and prices for hotels and attractions go way up. What I *did* like was taking a vacation in September or October, when kids were back in school, prices dropped and the temperature wasn't hot but was still usually pleasant enough for most outdoor activities except for swimming.