Roll the dice and live large. Double down and take the house. Know when to hold ’em; know when to fold ’em. And remember: Every high roller was once a gambling virgin, too.
Wynn, Lose, or Draw
Wynn Las Vegas, gazillionaire hotelier/art collector Steve Wynn’s latest, is Sin City’s new mecca.
Holy Roller: Pull an all-nighter on Omaha Hi-Low Poker. The seventeen live-action cooking stations at breakfast will revive you.
Blow It: On a table outside at Bartolotta Ristorante di Mare. Wonderchef Paul Bartolotta gets daily seafood deliveries from Italy.

Let It Ride
It’s racing season in Saratoga Springs — time to play the ponies. Rest up at the Gideon Putnam Resort, breakfast at Mrs. London’s (464 Broadway; 518-581-1652), then head to the track to place your trifecta, superfecta, and Pick 6 bets.
Holy Roller: If the stars are aligned, a $2 ticket could net you $15,000.
Blow It: On a soak at the Saratoga Mineral Spa & Salon and dinner at 43 Phila Bistro.
Better in the Bahamas
Kitsch is king at the Atlantis megaplex on Nassau. Play everything from craps to Caribbean Stud Poker under a Dale Chihuly-designed chandelier.
Holy Roller: The Bridge Suite costs $25,000 per night and overlooks shark pools and Mayan waterslides.
Blow It: On Cartier and Cuban cigars in the Crystal Court shopping arcade or cheap conch shell jewelry at the Bahama Craft Centre.
The Full Monte
From baccarat to baguettes, real playas play Monaco. Try your hand at chemin de fer, a complex game involving a passed shoe, multiple decks, and advanced math, at Les Casinos de Monte-Carlo.
Holy Roller: Can your offshore tax haven handle the Super Privé rooms?
Blow it: On belle epoque grandeur at the Hotel de Paris and dinner at Alain Ducasse’s three-Michelin-stars Le Louis XV.
Russian Roulette
Follow the oligarchs straight to the Casino Royale at Moscow’s Hippodrome (Begovaya Ulitsa 22, Korpus 1; +7-095-945-1410) where $10 buys you entree into the slightly scary world of Russian gaming. Don’t forget your passport and hotel registration. Do lose the jeans and wear as much bling as possible.
Holy Roller: Atone for the gambling at St. Basil’s.
Blow It: On hats, local chocolates, and other souvenirs at GUM in Red Square.

Shaken, Not Stirred
Fifty London is the chic members-only club (annual fee: 750 GBP) with two Jean-Georges restaurants and the one-and-only Salvatore’s bar. Blackjack and punto banco are the games du jour.
Holy Rollers: The casino walls are lined in silk; the tables are made of mahogany.
Blow It: On a park view suite at The Dorchester and champagne at Pengelley’s.
Hey. All it takes is a dollar and a dream.