Inaugurated in 1832, Old San Juan’s iconic Teatro Tapia is one of the oldest continuously operating theaters in the United States. Its neoclassical facade features a row of austere arches and solemn pilasters encasing balconets, all painted painted in white and Naples yellow; it certainly contrasts quite noticeably with the powder-blue structure of the Antiguo Casino just across the Plaza Colón. At the Teatro Tapia, you can ease yourself into one of its comfortable, red velour chairs and enjoy an intimate concert, a play or even a stand-up comedy show. Its three levels combined can seat up to 640 spectators, and its elliptical form encourages a clear view from every angle.