Since I am back at work from my last vacation of course all I can think about is the next one 🙂
One thing we have looked at is something that a good friend of mine did a few months ago. Her boyfriend works in Mexico, so he flew her and her kids down there and they all stayed in on of those Condo Hotels. They are actually pretty reasonable when you consider what you get. If you have the kind of money to spend it’s much better than a timeshare and are usually managed well when you aren’t staying in your suite.
I could see living in a few different condo hotels year round and just traveling to where ever the weather happened to be nicest at that time of year. Caribbean or Baja in the Winter, New York or Canada in the summer. The freedom would certainly be nice.