La Placita de Santurce is a covered food market square that spends its days selling produce and its Thursday and Friday evenings becoming one of the most atmospheric nightlife spots in San Juan. The transformation happens gradually from about six in the evening — stalls and small bars surrounding the square fill with locals and visitors, rum-based drinks circulate in plastic cups, and salsa music drifts through the air from competing speakers. By ten o'clock it's packed.
The crowd is genuinely mixed — San Juan residents who've been coming here for years alongside tourists who've made their way over from the hotel strip in Condado. The drinks are inexpensive by San Juan standards and the atmosphere is unselfconscious in a way that the more curated cocktail bars on Ashford Avenue are not. Get there early enough to find space at one of the outdoor tables; later arrivals stand in the square and that works fine too. The surrounding streets of Santurce have filled in with bars and restaurants, so the evening naturally extends outward from the Placita into the neighborhood. Walk home to Condado along Ponce de León when you're done — it's twenty minutes on foot and well-lit.