San Sebastian Festival - January

This festival is one enormous outdoor party, and one of the biggest celebrations in San Juan. San Sebastián Street in Old San Juan gets absolutely stuffed with stalls, crowds, food, alcohol, music, arts and crafts shows, and general revelry.

Ponce Carnival - February-March

The Ponce Carnival is the most celebrated and colorful festival on the island. It's also one of the oldest, dating back to the 1700s. 

Heineken Jazz Festival - May-June

One of the Caribbean's biggest Jazz fests, this annual festival is a Jazz lover's dream. The open-air Tito Puente amphitheater in San Juan's Hato Rey district is the ideal venue, and the four-day concert brings together contemporary Jazz masters.

San Juan International Billfish Tournament - August-September

Few game-fishing events in the Caribbean carry the clout of this annual tournament. The San Juan International draws deep-sea fishing anglers and game-fishing enthusiasts from around the globe.