The St. Regis is the best place to kick off the crawl for those who can get started right at 5 p.m. That's because each day at 5 p.m. one of the bartenders will saber complimentary champagne in the lobby. Then go inside the bar to gawk at some of the original architectural detail in the hand-carved wood ceiling. And consider ordering a Bloody Mary while you're there — the hotel claims to have invented the drink.

Next, head across the street to Off the Record, with its clubby decor perfect for those clandestine meetings between nearby White House staffers and Post reporters. Sip on seasonal cocktails or get in to the Mad Men spirit of the place and choose from a selection of bourbon, scotch and cognac.

The Old Ebbitt Grill was founded in 1856, and moved around before settling in to its current location on the 15th Street in the 1983. In spite of that the interiors remain decidedly old school with Victorian interiors and the restaurant contains memorabilia from its previous incarnations. Pull up to one of the four full service bars for a classic cocktail or cellared wines and some oysters from the raw bar.

D.C.'s official cocktail, the gin rickey, was invented at a bar that used to stand on the site of the current JW Marriott hotel. As an ode to its history, the hotel's 1331 Bar & Lounge offers the drink (it's even half-priced during happy hour).