If you’re looking to impress a date or to soak in some of DC’s rich history, this is the place. The wood-paneled bar—recently reopened after renovations—has hosted numerous presidents, Hollywood stars, and Washington insiders. The wine list is extensive, but we like the bar’s signature cocktails, including the Classic Manhattan and the Jockey Club Cocktail, a mixture of Blue Coat American gin, white crème de cacao, and lemon juice. Wednesday through Sunday after 8, a pianist plays lounge jazz on a Steinway that was a gift from the Kennedy family. The dress is casual, but jackets for men are required at the neighboring Jockey Club restaurant.