Puerto Rico Has the Longest Holiday Season in the World

By mid January all the cheer of the Christmas season has faded into a distant memory. Decorations are returned to their storage spots and empty champagne bottles have long made their way to recycling bins, leaving many of us in the quiet hush of the post-holiday blues. But not in Puerto Rico. The Boricuas are still holding strong with the holiday vibes. The little island tucked away in the middle of the Caribbean Ocean has the longest holiday season in the world. It begins in late November and stretches out across a lively 45-day celebration until it concludes in the third week of January.

In the heartland of Puerto Rico, the rolling hills and valleys buzz with festive preparations starting as early as October 1, but the unofficial start to the Christmas season arrives on November 19 with Discovery Day. This date remembers Christopher Columbus’s first landing on the island in 1493 during his second voyage to the New World. Known locally as “Día del Descubrimiento de Puerto Rico,” this official holiday marks the beginning of a jubilant period that crescendos past the traditional Christmas celebrations. 

Celebrations on the island continue well beyond Christmas and New Year’s Day. Puerto Rico celebrates El Día de Reyes or Three KIngs Day on January 6. Three Kings Day, a cherished day of gift-giving for many Latin American countries, celebrates the Three Wise Men’s visit to the newborn Jesus. The night before, Puerto Rican children collect grass or hay in shoeboxes and place these under their beds. Similar to putting cookies out for Santa, this act serves as a thoughtful offering for the Magi’s camels in the hope of exchanging it for presents.

Even after the passing of Three Kings Day, the Christmas season still is not over. Las Octavitas is a festive Puerto Rican tradition that extends the holiday season well into January. It begins on the eighth day after Three Kings Day and lasts for another eight days. It’s a time of joyous gatherings that combine music, dance, and communal festivities. Rooted in Puerto Rico’s Catholic heritage, Las Octavitas today is more a cultural celebration that reflects the island’s deep-seated spirit of community. 

The climax of Puerto Rico’s holiday season is the Fiestas de la Calle San Sebastián, affectionately called la SanSe by locals. The festival, named after Christian martyr San Sebastián, began in the 1950s as a way to celebrate San Sebastián’s feast day. It has since grown into an annual tradition where, over a long weekend, Old San Juan transforms into a haven of live music, spontaneous dancing and even circus performances. Nearly 400 artists and local musicians converge to participate in the festival. 

By day the streets are lined with vendors offering local delicacies, from savory lechón asado (roast pork) to sweet tembleque (coconut pudding). The rhythmic beats of bomba and plena music fill the air inviting everyone to dance while parades of cabezudos (big-headed figures) meander through the crowds as a nod to the island’s folklore traditions. By night the city pulses with concerts and parties that extend into the wee hours of the morning. 

This year the festival takes place from Thursday, January 18 through Sunday, January 21. Headliners Ednita Nazario, Víctor Manuelle, Wisin, La Sonora Ponceña and La Puertorrican Power will play along with other bands across four large stages set up at Plaza del Quinto Centenario, Plaza de Armas, Plaza Colon, and Plaza de La Barandilla. One of the best parts? Admission to the festival is free. 

This year’s celebration is expected to attract record breaking crowds to Puerto Rico, making navigating the city by car almost impossible. Your best bet is to stay in the heart of Old San Juan where you are steps away from the festivities (and steps back away to your room when you need a break from all the festivities). The city center is full of great hotels, but none better than Hotel El Convento. Housed in a restored 17th century convent, this hotel is an example of the old-world Spanish colonial architecture at its finest. The interior courtyard is shaded under the leaves of 300-year-old Nispero fruit trees. If you want to watch the festivities from a distance while lounging around a pool, the rooftop offers sweeping views of the historic city center as well a plunge pool. If you need a serene escape from the buzzing city, you are in luck. Guests can enjoy exclusive beach access at El Convento Beach Club located on its sister property. The world-renowned beach is a good reminder that you are in a tropical paradise.

Jennifer Simonson is a travel writer by trade and a lover of the world’s food, cultures, drinks and outdoor spaces by nature.