Tobacco Road is definitely a road well-traveled, but that’s what you get when you’re throwing a few back at Miami’s oldest bar (est. 1912). Sure, there’s a little grit, but it just adds the right amount of character to a night out with friends. Al Capone used to hang here when it was a speakeasy, and today you and your crew can hang during the hoppin’ happy hours, checking out excellent live music by blues, jazz, and rock bands. For spiffier confines, head upstairs to The Cocktail Collection, the Road’s renovated second-floor cabaret. There you’ll channel the spirit of the O.G.s themselves, straight off the set of Boardwalk Empire. Settle in for some classic cocktailing. Have the barkeep work you up a Drunken Dragon, which puts an Asian slant on a Presbyterian, layering yuzu, ginger, and bourbon. Don’t worry if the night seeps into the wee hours, there’s a menu of bar fare—wings, burgers, dogs—to keep you going. Or you might want to convene on a night when, say, Maine lobsters, mashed potatoes, and coleslaw are given away at speakeasy-era prices. Tobacco Road may be on the far side of the century mark, but it’s still looking better than some starlets at 22.