Rich vacations

Palms Springs

Monaco

The south of France

Vail and Aspen for skiing

To name a few . . .

everywhere from Cape Town to the South of France. It changes yearly depending on what's "in", but Monte Carlo is also pretty popular if a bit of a cliche.
Dubai is another place that the rich love - fast-paced & very glitzy.

And, for the past year, New Orleans, to show that the rich and famous have hearts too . . . as long as there's a video crew following along.

If you want a quiet retreat...rent a private island for a couple of weeks/months or an expensive villa.

Here's some really expensive stuff: http://www.unusualvillarentals.com/

If you want to get into the mind of the wealthy, check out BestLife magazine, which is for affluent men. Always has great things I drool over but never ever will be able to afford!

Monte Carlo; your own private villa in the South of France at somewhere like Cap d'Ail, or Nice; a five star hotel in Dubai, a beautiful Thai island.

Also, a lot of wealthy people are quite into "rugged" sort of stuff, depending on their level of fitness, like gliding, climbing and suchlike. Also, a lot of them like to go to more out of the way places, like Latin America, or African game parks, such as Serengeti.

So, it really depends upon the tastes and personality of your rich person.

Bora Bora in the South Pacific (Tahiti). Turtle Island in Fiji looks quite nice.

Sandy Lane Hotel in Barbados (for Christmas if you're really loaded).
I've stayed in the resort next door, it looks very nice.

The Plaza Hotel/Residences in NYC...I'm guessing

http://www.theplazaresidences.com/