Palm Beach, Fla.
In the sale Inflatable Arch 1920s, everyone who was anyone wintered in this playground for the privileged. Today, that still holds true. America's wealthy converge on this slim barrier island for the season, a several-week-long stretch of glittering charity balls and endless parties. Palm Beach has one professional butler for about every 500 residents, which might almost seem low, and more orchestras per person than any place else on the list, which, given the indulgent lifestyle, might seem surprisingly high. And don't forget the houses: it's Mediterranean mansion central.
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