Caroline’s Other Side

The historic Dr. Joseph Y. Porter House—a turquoise 1838 Victorian on the corner of Duval and Caroline streets—is like a fun-filled Russian nesting doll. On one side of its downstairs, the Porch, a craft-beer bar, holds its own. On the other side of the porch, Caroline’s Café serves casual lunches and dinners. But inside Caroline’s Café, you’ll find Caroline’s Other Side, a craft cocktail bar with a jazzy and vintage-inspired vibe. Patrons sit along lounge seating or at the bar itself, watching the mixologist shake up classic concoctions like a Ramon Fizz. The bartenders here are among the best in town, and the cocktail menu includes vintage favorites like Old Fashioneds and Moscow Mules as well as some specialty drinks. Before you leave, be sure to get your fortune told by the antique Zoltar arcade game.

In the land of piña coladas and light beers, The Other Side cocktail lounge is chiseling out new booze territory one ice globe at a time. Drinks, loosely inspired by the Keys, are like nothing else on the island. There’s the frothy Ramon Fizz, a mix of gin, lime, cream, egg whites, and fleur d’orange, or twists like the fennel martini, and for purists, a serious list of bourbon, whiskeys, and 16 rums. The small space feels a world away from the beach, with touches of old-school Hollywood glamour: a marble-topped bar, padded white leather bar stools, and a painting of a peacock tail fanned across one wall. When you need a break from the sun and throngs, this is the place to tuck in with a good book, or a good date (snag the chess board if you’re feeling ambitious).

Sip classic hand-crafted cocktails in this intimate lounge in an elegant historic mansion off rowdy Duval Street. Pull up a white-leather stool at the marble bar or settle in at a table on the porch to enjoy the evening breeze.