Fodor’s Travel. December 2023.

Hanging globe lights and little ceramic Christmas trees adorned the long family-style wooden dinner table. At El Pretexto culinary farm lodge in the scenic Cercadillo community in Cayey, Puerto Rico, I shared bowls of rice, beans, and pollo guisado (chicken stew) that the owner’s mother had cooked just minutes ago using their farm-fresh ingredients.

As the stars appeared in the night sky, the air in the mountainous region became cooler. Then, a group of four neighbors appeared with their cuatro, pandero, güiro, and guitar and broke into a song. Over the next few hours, I sipped on shots of pitorro (moonshine) and listened to upbeat aguinaldos (Spanish version of Christmas carols), swaying to the beats of maracas and clapping along to cheer them on. It was an impromptu Puerto Rican-style pre-Christmas party, and it was about to last for nearly two months.

On the island of Puerto Rico, Navidad lasts around 45 days, starting right after Thanksgiving Day in November, extending through mid-January, and culminating with the Fiestas de la Calle San Sebastián. Many Puerto Ricans (or Boricuas as they call themselves) start decorating their Christmas trees in November and don’t take them down for almost two months. Communities gather to light the municipality town squares, listen to folkloric music, and snack on street foods. Puerto Rico becomes a warm and festive winter wonderland during the holiday season.

If you want to make the happiest time of the year last for a few extra days, head to the tropical island and indulge in unique holiday traditions and festive events. With their jolly nature and positive attitudes, Boricuas are very welcoming of visitors and before you know it, will invite you over to join them for a party.

Here are some customs you should know about when celebrating the holiday season in Puerto Rico.

Boricuas don’t fa la la la la, they roll their tongues to le lo lai during Christmas time. There are three main genres of holiday music in Puerto Rico: aguinaldos (which means gift), religious tunes or villancicos, improvised trovas, and bomba and plena.

A parranda or trulla is the Boricua version of a Christmas carol. The first time I heard an aguinaldo (traditional Christmas song), I felt the excitement of holiday caroling to salsa beats interspersed with humorous country folk lyrics. The rhythmic beats lifted my spirits and got my feet moving instantly.

During days leading up to Christmas, families, neighbors, and friends gather and go around sing carols from door to door. This is usually late at night with a friendly intention to wake neighbors up, party at their house, and continue to round up more folks to the next place. To add to the element of surprise, parranderos round-up quietly with their instruments and burst into loud and jubilant music in front of a quiet home. The euphoric carol singers may go on till sunrise, and the group becomes bigger as the night goes on. Though the parrandas come unannounced, households are prepared to welcome them with snacks and refreshments throughout the season.

In the town of Cayey, you can listen to Boricua-style Christmas music any time of the day. The Casa de la Musica (house of the music), located off the main square, documents the rich musical history of the town and attracts musicians from around the island and the world to practice, play, and teach in an informal, open-to-the-public setting.

Christmas Eve: Nochebuena

On Nochebuena, or Holy Night, the number of parrandas escalate. Families gather to celebrate Christmas Eve with a traditional dinner of pasteles (which is more elaborate than tamale), pernil (whole roasted pork), arroz con gandules (rice with pigeon peas), and morcilla (black sausage), washed down with homemade coquito (Puerto Rican version of eggnog made with coconut milk). After dinner, they go to “Misa de Gallo,” or mass held at midnight or very early on Christmas morning. You can see live reenactment of the nativity scene at many churches around the island.

If you don’t get a chance to taste traditional Puerto Rican Christmas specialties at a home, there is Mesa Redonda cooking school and event space. The instructor, chef Stephanie Haddock, learned the recipes by watching both her grandmothers labor, grating yucca to make masa, stewing meats, and carefully packing the soft pillows in banana leaves. No family dinner is complete without pasteles.

Christmas Tailgate: Chinchorro

During the Christmas season, befriend some locals, hop in a car, and go on a chinchorro, the Puerto Rican equivalent of tailgating/ bar hopping through the many designated routes along the island. One of the most famous ones is the lechon (whole roasted pork) route through the Central Cordillera Valley, where dozens of local eateries offer traditional dishes in casual settings. You can sit at relaxing outdoor patios and picnic tables or take the food to go.

Typically, you will rent a party bus or driver, bring your music, drink mojitos, and eat at several locations throughout the day. While Puerto Ricans go on chinchorros on weekends and holidays, they are especially popular during the Christmas holidays. Many of the food stands offer traditional Christmas meals, so you don’t need to cook or clean up. You could also try longaniza (a chorizo-like local sausage), carne guisada al caldero (beef stew), pastel al caldero, a stew of green plantains and shredded pork, at an old-fashioned Puerto Rican jíbaro house turned restaurant–Casa Vieja in Ciales, which is decked up with Christmas decorations and boasts amazing views of the valley.

And if you don’t yet have friends in Puerto Rico to go on a chinchorro with, join Laura Ortiz, founder of Sofrito Tours. Ortiz offers gastronomic and cultural experiences, taking small groups along Ruta del Lechón or Cayey’s Pork Highway and guiding you to her favorite criollo dishes at traditional lechoneras. Along the way, you will also learn about local painters and musicians, visit a colonial church, and hike to a swimming hole in the Carite Forest.

On New Year’s Eve, everyone heads to one of the many pristine beaches around the island. As the clock strikes 12, you eat 12 grapes in 12 seconds or drop backward into the waves to keep the bad spirits at bay.

Block Party: Día de Reyes

On January 6, head to the town of Juana Díaz, a.k.a. the Bethlehem of Puerto Rico, to celebrate Three Kings Day—one of the largest Christmas season events on the island. On procession day, thousands of people dress as shepherds and gather to watch three costumed men ride horsebacks and parade down the streets, handing out presents and candy to kids. There’s a mass at the town square, followed by family-friendly festivities filled with music, food stalls, and local art.

Stop by Casa Museo de los Santos Reyes (Three Kings Museum) to see costumes, photos, sculptures, and wood carvings of the religious figures. El Día de Reyes or Epiphany has been celebrated in Puerto Rico since 1884 to mark the three wise men’s visit at Jesus’ birth. On the night before Three Kings Day, kids in Puerto Rico write letters to their favorite king, gather grass or hay in shoeboxes, and place them under their beds for the Magi’s camels or horses (as in the case of an island). Similar to the tooth fairy, they receive gifts in exchange the next morning.

The festivities in Puerto Rico continue for another eight days after Three Kings Day. During las Octavitas, Boricuas continue to throw parties and go on parrandas.

The longest holiday season in the world unofficially ends with Fiestas de la Calle San Sebastián—a grand art and music festival held in the third week of January. During the day, the streets in Old San Juan are filled with hundreds of local artisans selling everything from paintings to hand-made jewelry. In the evening, music, dancing, and concerts make the walled city come alive with choreographed performances.

Folkloric parades of vejigantes wearing vivid colored masks and cabezudos, small figures of important Puerto Rican archetypes, or individuals with an oversized head dance alongside stilt walkers and energized attendees. Las Fiestas de la Calle San Sebastián or la SanSe lasts from Thursday to Sunday and attracts people from all over the island.

While the Christmas festivities conclude and the decorations are stored away for a few months, other Puerto Rico celebrations continue. The town of Ponce hosts one of the longest celebrated carnivals in the Caribbean, which ends on Fat Tuesday around February or March.

~ Written for and published by Fodor’s Travel. All rights reserved.