Puerto Rico has one main export: music. Puerto Ricans are raised on music and dance. It’s no surprise, then, that finding free outdoor concerts is easy, as long as you know where to look.
Old San Juan
There are several free concerts during the week in the Old City. On the Paseo de la Princesa, bands and artists perform on Saturdays and Sundays from mid-afternoon to 5-6 pm. The short street between the south-facing fortifications of the Old City is a farmers’ market, festival, and street fair all rolled into one. At the center of the activity is a stage that hosts various acts, ranging from reggatone to salsa.
At the top of Old San Juan, near El Morro, Ostra Cosa offers nightly entertainment in an open-air plaza. Cabaret and salsa are the most common offerings. Navigate to the western end of Calle San Sebastián (at the intersection of Calle del Cristo) and listen to the music. From 5:00 p.m. to 12:00 a.m., generally.
The Old City also hosts monthly and annual events, such as the legendary San Sebastián Street Fair. Plaza Colón holds monthly arts and crafts festivals with music, dance, and food. Plaza de Las Armas also hosts monthly events including free music and performing arts.
Condominium
Condado’s Ventana del Mar is a hub of activity on Sundays. Twice a month, the park hosts a free jazz festival with dozens of vendors, food carts, and dancing. Generally, the activities start around 10 am and continue until 5-6 pm. Vendors represent a variety of crafts and art forms, including artisan baked goods and organic foods, in addition to traditional artisan offerings.
green Island
The city of Carolina holds a weekly jazz festival behind Walgreen’s on Friday and Saturday nights in the summer. Depending on the schedule, free buses operate between the parking lot adjacent to the Munoze Airport and Punta Las Marías, providing services to all hotels. The quality of the performers is on par with the great jazz festivals in Puerto Rico. The artists, in the purest Puerto Rican style, fuse jazz inspired by New York and New Orleans with Caribbean influences. The stage area and the music and lighting equipment are set up for large, stadium-sized audiences.
Santurcio
La Placita is a relatively unknown local favorite for visitors in the Tourist Zone. The Gazebo hosts a weekly salsa band. La Placita is located between Dos Hermanos and Duffault Street, and during the day it functions as a farmers market. At night, it adopts a party atmosphere. Dozens of bars and restaurants are located in a small two-block area, giving La Placita a min-mardi gras atmosphere most weekends.
Ultimate Car
On weekends during the day, the Ultimo Trolley beach attracts bands of local volunteers at the gazebo adjacent to the beach parking lot. These are authentic Puerto Rican salsa bands using traditional Puerto Rican musical instruments. Band members gather in the gazebo (apparently anyone can get in on the music making) and perform traditional Puerto Rican standards for the crowd for free. Ultimo Trolley is located between Ocean Park and Punta Las Marías.
Conclution
The music never stops in Puerto Rico. Requiring an audience fee to listen to live music in San Juan is the exception, not the rule.