Fiestas de la Calle San Sebastián is a must if you want to celebrate Christmas, art, music, and food Puerto Rican-style, all the way. From January 15–18, 2026, Old San Juan transforms for Fiestas de la Calle San Sebastián, drawing more than one million attendees to the largest cultural event in the Caribbean.

Live music fills five performance venues, while street performances and parades flow through the historic city. Artisans line the streets selling handmade work, folkloric music and dance spill into every corner, and the air is thick with Puerto Rican food delicacies, cocktails, and cold drinks.

Originally a street-wide celebration honoring Saint Sebastián, observed by the Catholic Church on January 20, the festival has grown into something extraordinary. I don’t think you’ll ever see so many people dancing, smiling, and eating all at the same time. It’s an amazing experience. Well organized, safe, and full of joyful energy from people arriving from all over the globe.

Transportation is easy, too. The first day offers free transportation from key locations throughout the San Juan metro area, including the urban train. On the second and third days, round-trip transportation from the metro area to Old San Juan is just $5