Las Fiestas de la Calle San Sebastián (San Sebastián Street Festival) turns beautiful Old San Juan into a giant street fair with parades and entertainment that ends Puerto Rico’s Christmas season, one of the world’s longest.
Las Fiestas de la Calle San Sebastián 2026
Las Fiestas de la Calle San Sebastián 2026 is on Calle San Sebastián, Plaza Colón, Plaza de la Barandilla, Plaza del Quinto Centenario, La Perla and all over Old San Juan, Puerto Rico; from Thursday-Sunday, January 15-18, 2026. Parades, with their wonderful Puerto Rican cabezudos (big heads) march from Plaza Colón or El Castillo de San Cristóbal to la Plaza del Quinto Centenario. They usually start around 5 or 6pm with the big Desfile de los Cabezudos on Sunday. Cultural groups perform throughout the early evening. 🇵🇷
This is the performance schedule, but this is Puerto Rico, so things often change at the last minute. Just go and have a good time.
Las Fiestas de la Calle San Sebastián 2026 in Old San Juan, Puerto Rico, opens on Thursday, January 15, 2026 in Plaza Colón at the entrance to Old San Juan with Trio Homenaje (bolero and música Jíbara) at 4:30pm, Los Pleneros de Severo (plena) at 6pm, Luian (reggaeton & trap) at 8pm, and Algarete (punk rock) at 9:30pm. In Plaza de la Barandilla (below Calle Tanca, the street with La Verguenza chinchorro at the top) Trio Los Andinos (boleros and Andean folk) perform at 5:30pm, Tuna de Cayey (Tuna Puerto Rican choral music) at 7:30pm, and Michelle Brava (salsa) at 9:30pm. 🇵🇷
Las Fiestas de la Calle San Sebastián 2026 in Old San Juan, Puerto Rico, continues on Friday, January 16, 2026 in la Plaza del Quinto Centenario, the plaza with a totem and stairs next to the old Ballajá barracks, with Plena Libre (plena) at 6pm, Miriam Cruz and her Orchestra (Dominican merengue) at 8pm, and Pedro Capó (pop) at 10pm. 🇩🇴 🇵🇷
Las Fiestas de la Calle San Sebastián 2026 in Old San Juan, Puerto Rico, continues on Saturday, January 17, 2026 in la Plaza del Quinto Centenario, the plaza with a totem and stairs next to the old Ballajá barracks; with La Tribu de Abrante (bomba and plena fusion), Tito Nieves (salsa), and Hermes Croatto (pop folk). 🇵🇷
Las Fiestas de la Calle San Sebastián 2026 in Old San Juan, Puerto Rico, ends on Sunday, January 18, 2026 in la Plaza del Quinto Centenario, the plaza with a totem and stairs next to the old Ballajá barracks; with Grupo Manía (merengue), Victor Manuelle (salsa), Juanes (Colombian pop), Andy Montañez (salsa), Ednita Nazario (pop rock), and Jowell y Randy (reggaeton pioneers). Teatro Tapia, below Plaza Colón, presents the Third San Sebastián Cup of Trovadores. Trovadores are Puerto Rican troubadours who improvise on the spot. Their competitions are a lot like rap battles. We don’t know which came first, but they are very entertaining if you speak Spanish.
Las Fiestas de la Calle San Sebastián
It’s Puerto Rico’s most popular festival. Locals call it the SanSe. That’s a little joke. Sanse is Puerto Rican slang for the island’s unique blend of West African, Central African, and European religions the locals call Espiritismo.
Calle San Sebastián is a beautiful colonial street of bars and restaurants. The festival also includes a street fair of Puerto Rican artisans. The party spills over into La Perla, the beloved shanty town along the ocean just beyond the city’s walls. La Perla is cool, but you must be respectful of the locals. It’s a little more relaxed at this time, but normally you shouldn’t take pictures in La Perla without asking permission. No definitely means No.
La Factoría, one of the world’s 50 best bars, is on Calle San Sebastián. It is one of the best places to dance salsa in San Juan on Sunday and Monday nights. El Jibarito restaurant has some of the best Puerto Rican food on the island. La Garita restaurant overlooks La Perla. La Verguenza chinchorro has third-floor seating that also overlooks La Perla. By the early morning, lots of people catch a quick nap on the grassy field in front of El Morro.
Puerto Ricans come to the SanSe from all over the island and across the diaspora. It’s the time to be home. If the walls of the city could talk, there would be many wonderful stories to tell. It’s probably a good thing that walls don’t talk. 🥳🥳
Daytime is more family oriented. Hordes of teenagers show up in the evening. Puerto Rican teenagers have lots of style. They are very cute.
Puerto Rico Has One of the World’s Longest Christmas Seasons
Christmas season starts in Puerto Rico on November 19, Discovery Day. Things build up past Christmas to Three Kings Day, the Hispanic gift-giving day.
The season continues with Las Octavitas, the octave of Three Kings. Octaves are a remnant of colonial Catholicism which celebrated festivals for eight days, not just one. Celebrating las Octavitas remains part of Puerto Rican identity.
Las Octavitas gets us to the SanSe. ¡WEPA!
Then we all go back to work, counting the days until next November.