Qué Pasa, the official visitor's guide, has listings of events in San Juan and out on the island. For daily listings, pick up a copy of the English-language edition of the San Juan Star. The Thursday edition's weekend section is especially useful. For the gay scene, check out the monthly Puerto Rico Breeze; the free newspaper is found in many businesses, especially in the Condado area.
In Old San Juan, Calle San Sebastián is lined with bars and restaurants. Salsa music blaring from jukeboxes in cut-rate pool halls competes with mellow Latin jazz in top-flight nightspots. Evenings begin with dinner and stretch into the late hours at the bars of the more upscale, so-called SoFo (south of Fortaleza) end of Old San Juan. Well-dressed visitors and locals alike often mingle in the lobby bars of large hotels, many of which have bands in the evening. An eclectic crowd heads to the Plaza del Mercado off Avenida Ponce de León at Calle Canals in Santurce after work to hang out in the plaza or enjoy drinks and food in one of the small establishments skirting the farmers' market. Condado and Ocean Park have their share of nightlife, too. Most are restaurant-and-bar environments.
Just east of San Juan along Route 187, funky Piñones has a collection of open-air seaside eateries that are popular with locals. On weekend evenings, many places have merengue combos, Brazilian jazz trios, or reggae bands. In the southern city of Ponce, people embrace the Spanish tradition of the paseo, an evening stroll around the Plaza las Delicias. The boardwalk at La Guancha in Ponce is also a lively scene. Live bands often play on weekends. Elsewhere en la isla, nighttime activities center on the hotels and resorts.
Wherever you are, dress to impress. Puerto Ricans have flair, and both men and women love getting dressed up to go out. Bars are usually casual, but if you have on jeans, sneakers, and a T-shirt, you may be refused entry at nightclubs and discos.