The elegant Cafe Milano in Georgetown is a who's-who-of-DC. From government officials to journalists to diplomats, the customers here can be as notable as the restaurant's exceptional Italian menu. Nearly all of the pasta is homemade daily, including the must-try pappardelle gucci with veal ragout, seasonal mushrooms, and white truffle oil. You'll also want to order a glass of Sangiovese or a classic cocktail (Aperol Spritz, Negroni) as you rub elbows with some of the city's most famous faces. Unless you're looking to make connections, the prices might push you to make this a special occasion-only spot.