Puerto Rico has one main export: music. Puerto Ricans are raised on music and dance. It is no wonder, then, that finding free open-air concerts is easy, provided you know where to look.
Old San Juan
There are several free concerts during the week in the Old City. On Paseo de la Princesa, bands and artists perform on Saturdays and Sundays from mid-afternoon til 5–6 pm. The short street between the Old City’s southern facing fortifications is a farmer’s market, festival, and street fair all in one. At the center of the activity is a stage which hosts various acts, ranging from reggatone to salsa.
At the top of Old San Juan, near El Morro, Ostra Cosa hosts nightly entertainment in an open-air plaza. Cabaret and salsa are the most common offerings. Navigate to the far western edge of Calle San Sebastian (at the intersection of Calle del Cristo), and listen for the music. 5 pm til midnight, generally.
The Old City also hosts monthly and annual events, such as the fabled San Sebastian Street Fair. Plaza Colon holds monthly arts and crafts festivals with music, dance, and food. Plaza de Las Armas also hosts monthly events including free music and performance art.
Condado’s Ventana del Mar is a hub of activity on Sundays. Twice monthly, the park hosts a free jazzfest with dozens of vendors, food carts, and dancing. Generally, the activities start around 10 am and continue til 5–6 pm. Vendors represent a range of crafts and artforms, including artesan baked goods and organic food in addition to traditional craft offerings.
The City of Carolina holds a weekly jazzfest behind the Walgreen’s on Friday and Saturday nights in the summer. Depending on the schedule, free buses operate between the parking lot adjacent to Munoze Airport and Punta Las Marias, providing services to all hotels. The quality of the performers is on par with Puerto Rico’s great jazzfests. The performing artists, in true Puerto Rico fashion, fuse New York and New Orleans inspired jazz with Caribbean influences. The staging area and music and lighting equipment are set up for large stadium-size audiences.
La Placita is a local favorite relatively unknown to visitors in the Tourist Zone. The Gazebo plays host to a weekly salsa band. La Placita is located between Dos Hermanos and Duffault Street, and during the day functions as a farmers’ market. By 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 nearly every weekend.
On weekends during the day, the Ultimo Trolley beach attracts local volunteer bands in the gazebo adjacent to the beach parking lot. These are authentic Puerto Rican salsa bands using traditional Puerto Rican musical instruments. The band members assemble at the gazebo (apparently anyone can participate in the music-making), and perform traditional Puerto Rican standards to the crowds for free. Ultimo Trolley is located between Ocean Park and Punta Las Marias.
The music never stops in Puerto Rico. Requiring payment from an audience to hear live music in San Juan is the exception, not the rule.