On all the vacations I've taken - and I generously count the travels from one side of the country to the other, going from school to work and back - it's always been about the journey more than the destination; or, like the last ones, the destinations (a slew of national parks etc) were part of the journey. The result, as far as money is concerned, is that I can go far, do a lot, and do it fantastically cheap - roughly speaking, it just costs 10-15 cents in gas (okay, maybe 20-25 in canada) per mile, unspecified maintenance issues, and a small amount of overhead for food.
But now that I can afford it, I would love to take the kind of vacation where you minimize travel time and try to spend time in an actual destination. Still looking to make it inexpensive, but not going as far as being cheap.
Maybe next winter I'll fly to Hawaii or something. Rent a car, and if I'm by myself, sleep in it by the best places to get sunrises and sunsets.
Experiences don't get a pass as far as spending goes - but when you have no debt, lots of savings and continue saving, well... whatever makes you happy doesn't really get a lot of judgment, fiscally. You're set, you know what you're doing, you know the costs.
Putting that shit on a credit card when you're already in debt is another story entirely.