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 restaurants 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.
By law, all casinos are in hotels, primarily in San Juan. The government keeps a close eye on them. Dress for the larger casinos is on the formal side, and the atmosphere is refined. Casinos set their own hours but are generally open from noon to 4 AM. In addition to slot machines, typical games include blackjack, roulette, craps, Caribbean stud (a five-card poker game), and pai gow poker (a combination of American poker and the Chinese game pai gow). Hotels with casinos have live entertainment most weekends, as well as restaurants and bars. The minimum age to gamble is 18.