The Pool After Dark
Beach and Steel Pier
Lounge in The Chelsea
By train: Atlantic City, New Jersey (2 hours from NYC)
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.
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.
By plane: Las Vegas, Nevada (6 hours from NYC)
Satiate your need for speed even before your first cup of coffee at Pole Position Raceway (4175 S Arville St; 702-227-7223, polepositionraceway.com/vegas; $25 per race), where electric go-karts cruise at speeds of up to 45mph. "It's common for professional racers to show up here," says company president Ken Faught. "We've had everyone from NASCAR's Kurt and Kyle Busch, Kevin Harvick and Juan Pablo Montoya to IndyCar's Al Unser Jr. and Paul Tracy." Afterward, experience what it's like to be Iron Man with a SkyJump free fall, which sends you hurtling from the 108th floor of the Stratosphere Hotel (2000 Las Vegas Blvd South; 800-99-TOWER,skyjumplasvegas.com; $99, free shuttle available from the Raceway). Head south to soak up some Sin City--style culture as you gawk at one of the largest assemblages of authentic Elvis-owned items, including some of the King's more questionable wardrobe choices (a mermaid suit), at The King's Ransom Museum (Imperial Palace Hotel, 3535 Las Vegas Blvd, thekingsransom.com). Or hit the Pinball Hall of Fame (1610 E Tropicana Ave, pinballmuseum.org; free), where you can play more than 200 games from the past 50 years. Come nightfall, visit the kind of CatHouse (Luxor, 3900 Las Vegas Blvd South; 702-262-4228, cathouselv.com) where $39 actually buys you something—in this case, a three-course dinner at Iron Chef Kerry Simon's 19th-century-bordello-inspired playpen of traditional American food with a sexy twist.
It doesn't get more Playboy than the Palms Casino Resort (4321 W Flamingo Rd, 866-942-7777; from $159), where you'll find the Hugh Hefner Sky Villa, 95,000 square feet of gambling space and an in-hotel tattoo parlor.
By car: Mashantucket, Connecticut (3 hours from NYC)
A leisurely drive up I-95 doesn't offer much in the way of stimulation, until you reach lucky Exit 92. Originally founded as a bingo hall by the Mashantucket Pequot Tribal Nation, Foxwoods (350 Trolley Line Blvd, Mashantucket; 800-FOXWOODS)—together with the MGM Grand at Foxwoods—now constitutes one of the world's largest casinos. Get some sustenance for the long night ahead at David Burke Prime(davidburkeprime.com), featuring a not-so-typical $5 Burger Event (Thu--Sat noon--4pm).Then, lap up some liquid courage at The Scorpion Bar (860-949-4847,thescorpionbar.com), and hop a shuttle to the MGM Grand (240 MGM Grand Dr; 866-646-0050, mgmatfoxwoods.com). Head directly to Shrine (shrinemgmfoxwoods.com)for an Asian meal and a possible celebrity sighting; Lindsay Lohan and Snooki have both been spotted cutting loose here.
The country-lodge-like Two Trees Inn (foxwoods.com, $145--$625) offers a New England experience in the middle of all the action, with 24-hour shuttle service to and from the complex's six casinos.