London, England

Game on: To understand the depth of London's gambling heritage, consider this: Sir Thomas Neale, the 17th-century courtier who doubled as a croupier for English royalty, has several streets named in his honor. West End gambling institutions such as Crockfords (the world's oldest private gaming club, established 1828) and Aspinalls were once the preserve of the Brit establishment. These days, club guests can sit down at the blackjack table for a minimum £25 bet, but know you'll be up against gamblers who won't flinch at throwing down thousands of pounds in the pot. More modest bankrolls are accommodated at casinos like the Grosvenor Victoria, where many U.K. pros have earned their Texas Hold 'Em chops in "The Vic" card room. The class system is, however, alive and well at flagship racing events such as the Epsom Derby, held every June in nearby Surrey: The royals, aristocrats, and well-connected wag their top hats from the Queen's Stand, the most expensive enclosure, while the party crowd heads to the Hill, a free-to-commoners area in the middle of the racetrack.

Inside bet: Guests of the legendary Ritz London get a complimentary membership to the Ritz Club Casino during their stay. Membership ordinarily costs £1,000—chump change to the international oligarchs and oil barons who frequent its gilded salons.

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