By train: Atlantic City, New Jersey (2 hours from NYC)
Do this
Anyone who has grown up playing Monopoly knows that Boardwalk is the ultimate destination. Borrow one of the Chelsea Hotel's bicycles (free for guests; see info below) or use your own two feet to navigate the four-mile walkway that is home to seven casinos, including the Tropicana (2831 Boardwalk; 609-340-4000,tropicana.net). The Trop's decor conjures Old Havana, but its gaming is state-of-the-art, boasting more than 3,100 slots, a poker room, an Asian gaming pit and 169 table games, including newer species like Boston five-stud and three-card poker. Those who prefer not to lose their shekels as Tony Stark can watch the high-stakes drama from the Rumba Lounge, which offers a full panoramic view of the casino floor. Eastward and seaward, The Pier Shops at Caesars (One Atlantic Ocean, 609-345-3100) give new meaning to high-end shopping, with two stories of specialty stores. Adrenaline junkies can go from zero to 225mph in 1.5 seconds at Steel Pier (1000 Boardwalk; 609-345-4893, steelpier.com) via a trip on slingshot ride the Rocket ($20). Before your weekend ends, haul over to The Pool After Dark (Harrah's Resort, 777 Harrah's Blvd; 609-441-5233), where late-night dancing, drinking and debauchery have seduced the likes of Snoop Dogg, Kim Kardashian and now you.
Stay here
Take the ACES train (acestrain.com) to A.C. and cab it to The Chelsea (111 S Chelsea Ave, 800-548-3030; $145--$250).The fifth floor entertainment playground has a champagne-and-cocktail lounge.