The sounds of Santiago de Cuba alone will reel you in—trumpets, bongos, guitars, clapping, stomping, you name it. Live music is happening, happening, happening, all over this vibrant city, but one of the best places to catch traditional beats is at Santiago’s Casa de la Trova. The doors are flung wide to spirited Heredia Street late afternoon ’til late night. Hit the small dance floor, cram yourself onto one of the narrow benches, or join the crowds grooving right outside.
Park Yourself in Lively Cespedes
There’s little shade in central Cespedes Park, so the best time to hang out is at dusk, when temperatures drop and throngs of locals arrive to talk, flirt, drink, play music, and more. As you crisscross the city it’s inevitable that you’ll find yourself on a bench here, taking in the nightly commotion. The bronze bust of Carlos Manuel de Cespedes at the park’s heart makes an excellent meeting place, too.
Drink at the Ultimate Sunset Spot
Writer Graham Greene’s character Wormold from Our Man in Havana stayed in the elegant Hotel Casa Granda; the scribe himself loved to relax on the street-side terrace. But—apologies to Greene—though the lower terrace is nice, the fifth-floor garden bar is the real stunner. It’s well worth the $2CUC fee (applicable to a drink) for a chance to kick back on high with a rum drink, gazing out to the harbor and beyond while the late rays of sun turn the city golden. The angel statue tops nearby Catedral Nuestra Señora de La Asunción (Our Lady of the Assumption Cathedral), best viewed from the terrace.
Climb the Padre Pico Steps
Calle Padre Pico is one of the most famous streets in Santiago, thanks to its famous stairs. Commissioned in 1899 by Emilio Bacardi Moreau (yes, of the famous Bacardi rum distillery), the staircase has become a city symbol. The steps stand at the gateway to Tivoli, Santiago’s picturesque old French quarter, settled by Haitian colonists in the late 18th century. Walk them as you wander through, snapping photos.