Mad Men Manhattan

On the Show: The Drapers attend a star-studded party at the (since closed) former speakeasy Stork Club, where Betty Draper learns from the comedian and star of one of Don’s advertisements, Jimmy Barrett, that her husband is having an affair with Jimmy’s wife and manager, Bobbie Barrett. (Season 2)

In Reality: Opened as a speakeasy in 1930, the historic restaurant 21 is the perfect spot for a three-martini lunch. In contrast to the adulterous atmosphere at the Stork Club on the show, the upstairs dining room at 21 is a popular spot for wedding proposals.

Best If You’re: Entertaining clients, or mixing business with pleasure.

On the Show: Betty (clad in a new fur coat) and Don celebrate Valentine’s Day in a palm-filled hotel dining room at the (now defunct) Savoy Hotel. After running into Betty’s old college friend turned “working girl,” the Drapers retire to a romantic evening in one of the hotel’s lavish suites. (Season 2)

In Reality: An ideal stand-in, the luminous dining room at the palace-like (and newly renovated) Plaza Hotel is where Eloises-in-the-making take afternoon tea and couples dine for special occasions.

Best If You’re: Using money to mend marital woes. It wouldn’t hurt to walk down the street to Saks Fifth Avenue for a mink for the missus.

On the Show: Sterling Cooper partner Roger Sterling calms his nerves about landing the Nixon account over a lunch of oysters and martinis. When the elevator at the Madison Avenue office is out of order, Sterling is forced to climb all 16 floors back to work—and promptly vomits at his clients’ feet. (Season 1)

In Reality: Under the main terminal near the Grand Central Dining Concourse, the beloved Oyster Bar is a sea of suits after work—and has one of the biggest and freshest selections of the briny shellfish in the city.

Best If You’re: A partner at an advertising firm with an expense account. Don’t let the diner décor fool you—the menu isn’t cheap.

On the Show: Don Draper lives at the Roosevelt while estranged from his wife. When his children spend the night, they order celebratory milkshakes and hamburgers in bed. (Season 2)

In Reality: A Madison Avenue landmark, the 1924 hotel caters to business travelers in Midtown. While it’s no longer the bastion of bachelor luxury, the new mad46 rooftop lounge does add cachet.

Best If You’re: A philandering executive—the hotel itself is even attempting a double life, with staid corporate meetings downstairs and rooftop cabanas upstairs.

On the Show: Even the most sophisticated women go giddy for the Pierre. Trudy Campbell, the overzealous wife of Sterling Cooper account executive Pete Campbell, insists the fixtures in her bathroom are just like the ones at the famed hotel. (Season 1)

In Reality: This stylish Midtown hotel continues to be the apotheosis of chandeliered elegance thanks to a $100 million renovation.

Best If You’re: A well-bred wife on a New York shopping trip.

On the Show: Retail heiress Rachel Menken hires Sterling Cooper to revitalize the image of her family’s store. The business relationship is complicated when Rachel and Don have an affair. (Season 1)

In Reality: Just as Menken’s department store suffered a retail slump (Season 1), so too did Bergdorf Goodman in the 1960s. The luxury department store has been outfitting ladies who lunch since 1906; underwent a major renovation in 2002; and today does a brisk business.

Best If You’re: A guilty husband looking to cajole your wife with a fancy gift.

On the Show: Sterling Cooper employee Peggy Olson becomes a copywriter and invites the office to P. J. Clarke’s to celebrate. Much twisting (the dance and the plot) ensues. (Season 1)

In Reality: A regular stop for tourist bar crawls and after-work meet-ups, this 130-year-old hangout typically has barely enough room to stand in, let alone dance. Frank Sinatra was a regular; Buddy Holly asked Maria Elena Santiago to marry him over a meal at the famed pub; and Nat King Cole called the bacon cheeseburger “the Cadillac of burgers.”

Best If You’re: Celebrating the five o’clock whistle (and the office is fresh out of gin).

On the Show: Sterling Cooper secretary-turned-copywriter Peggy Olson meets her ill-mannered date in a gritty watering hole frequented by office girls and their overzealous suitors. (Season 3)

In Reality: This SoHo pub, said to be a drinking establishment since 1847, draws the real cogs of the corporate machine (it’s definitely not for expense account types). While the bar’s bones and old-fashioned patina remain intact, it is surrounded by chic boutiques—and often filled with tourists.

Best If You’re: A giggling gal Friday with a taste for the hard stuff.

On the Show: Don Draper meets his mistress, Bobbie Barrett, at Sardi’s restaurant after she and her husband, Jimmy Barrett, celebrate his new television show. (Season 2)

In Reality: The caricatures, leather banquettes, and celebrity status of this Theater District favorite remain unchanged.

Best If You’re: Starting a new business venture, or new affair.

On the Show: Don Draper’s eight-year-old daughter, Sally, makes a mean Bloody Mary. (Seasons 1 and 2)

In Reality: The brunch classic Bloody Mary (called a “red snapper” here) was conceived at this New York society club and hidden gem. Enjoy one at the beautiful wood bar as you stare at the namesake King Cole mural by Maxfield Parrish.

Best If You’re: A silver fox with a soft heart and a penchant for fine art and booze.