Vacation, or way of life?

A good friend of mine has what seems like the perfect situation. She and her husband are retired and they have a BEAUTIFUL home in the Chicago suburbs right off of a forest preserve. It's amazing. They also have a really nice condo in Florida right off the beach. I've never been there but I've seen the pictures. In the summer they stay in Chicago, in the winter they move everything down to Florida. That just seems so perfect, but at the same time, I've thought about doing something like that, and when I think hard about it I wonder if that wouldn't get boring after a while. It's still the same old places every year. The only benefit is that in the winter you're not living in an icebox. Taking vacations and renting an Orlando vacation home rental seems like a better option to me, although it's true that I can't afford to do it ALL winter, so I do still have to come back and live in an icebox.