In a real fantasy world, I think I'd spend about a quarter of my time bouncing 2-3 weeks at a time among all the Disney resort properties all over the world, (WDW, DLR, Paris, Hong Kong, Tokyo - did I get them all?).
Another quarter of my time would be spent seeing places around the world that I might not otherwise have the time or money to see. For example, I'd like to see a redwood forest, visit the Great Wall of China, visit all 30-40 some odd cultural areas of China, visit at least one area of every country in the world, etc. I'd especially like to see all important monuments of all kinds everywhere, and also see how people of all kinds really live day to day.
Still another quarter (perhaps a bit less) would be "adventure" vacations, such as those offered by Disney travel, or all-inclusive vacations such as caribean all-inclusive resorts or cruises, etc.
The last quarter would be working from a home base on whatever interested me at the moment. Study something new. Build something with my hands. Charity work. Live performance production. Whatever.
From a practical standpoint, even being wealthy, this is not possible to do and still maintain what I consider to be healthy family relationships, and let the kids grow up in some more-or-less "normal" healthy world where they have friends, we have some kind of social interaction, etc.
So I suppose that even if we were wealthy, we wouldn't be able to spend more than a few weeks at a time maybe half a dozen times a year doing stuff like in the first three quarters described above. I'd probably want to split them more or less equally three ways, though.
I suppose to answer the original question, that would amount to 2-3 weeks about twice a year, but not always in Florida.
