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Chef Martin Louzao helped elevate San Juan’s dining scene in recent years with a duo of high-concept restaurants, Cocina Abierta and Oriundo. His latest venture, Café Caleta, a small tavern with countryside vibes, has an enticing international menu featuring French-style slow-cooked lamb, Japanese tamagoyaki eggs, and Argentinian beef empanadas. Local flavors shine as well: Don’t miss the Mallorca sandwich, made with a beloved Puerto Rican sweet bread (a recipe that was adapted from Spain’s ensaïmada pastry) filled with country ham, locally produced Ausubal cheese, tomato, and chives. The cafe spills into a charming cobblestoned street in Old San Juan, just steps away from the city’s main cathedral, the Basílica Menor de San Juan Bautista.

Old San Juan is filled with unremarkable souvenir shops, yet hidden among them is the one-of-a-kind Olé, a highly regarded maker of Panama hats and woven fedoras. Its owners have been perfecting their craft since 1977, and you will often see the founder’s daughters, Ingrid and Christinne Jeffs, at work at the back of the narrow space, adjusting the circumference of a hat on a special mold, or adding one of dozens of fabric trims. The women are known to wax poetic about headwear, explaining that most of their models are woven by hand in Ecuador, a process that can take months, then finished on-site. Past customers include David Spade, Carlos Santana, and Mick Jagger.

Set in a handsome neoclassical building with doric columns and arched windows, the Museo de Arte de Puerto Rico (MAPR) is the largest museum in the Caribbean — and arguably the most compelling. Its sleek white-walled galleries hold art dating back to the 17th century; standouts from the permanent collection include contemporary pieces by Puerto Rican artists such as Carlos Dávila-Rinaldi, whose pop-art paintings explore themes like violence and racism, and Rafael Trelles, who paints fantastical scenes to illustrate humanity’s fragmented sense of reality. After your visit, spend some time in the 2.5-acre garden in the back, dotted with sculptures and lush autochthonous trees.