Holiday Festivities During Vacation in the United States and Puerto Rico

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San Juan Christmas lights

If you’re the type of person who starts playing Christmas music in November and can’t bear to take down their tree until long after New Year, you might be comforted knowing there’s an entire U.S. territory full of people who feel the same. Fly just a few hours southeast of Florida to Puerto Rico, the archipelago where Christmas lasts a lengthy 45 days. The festivities kick off just after Thanksgiving and continue through the latter half of January, ending with the celebration of Fiestas de la Calle San Sebastián. Needless to say, December 25 alone just isn’t enough for most Puerto Ricans.



If you’re visiting the Caribbean islands from the mainland, you’ll enjoy the familiar sights of Christmas lights — head to Old San Juan for a stunning display. You’ll also spot Santa Claus decorations and traditional Nativity scenes arranged in the towns. However, if you’re used to white Christmases and building snowmen, the holiday season will feel different in Puerto Rico. Expect warm and sunny weather throughout the weeks-long celebration.

Enjoy these winter holidays in Puerto Rico

Festival of San Sebastián

In many places around the world, Christmas Day is the peak of the winter holiday season. But in Puerto Rico, the 25th shares the spotlight with several other important dates. First, on Christmas Eve — known locally as Nochebuena or Holy Night — families customarily celebrate with a traditional Puerto Rican meal, followed by a late-night mass service. Families remain together through Christmas Day when they exchange gifts, much like in most other parts of the U.S. Similar to the mainland, you’ll also find lively parties and fireworks displays to ring in the new year. However, the fun doesn’t stop the following morning like it might where you’re from.

Just a few days later, many Puerto Rican families prepare for Three Kings Day, which officially lands on January 6 every year. According to tradition, children place a box filled with grass under their bed or Christmas tree. The next morning, they wake to find presents next to their boxes. You can think of the festivities as a second Christmas. 



Finally, the winter holiday season finishes with a bang during Fiestas de la Calle San Sebastián. This usually falls within the second or third week of January. The festivities last for days, complete with vibrant street parties and parades — vastly different from the north, where it’s more common to stay home by the fire in the dead of winter.

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How to celebrate like the locals

family serving Christmas meal

While each winter holiday in Puerto Rico has distinct traditions, there are a few activities that you’ll find scattered throughout the season. One example is the parranda — Puerto Rico’s take on caroling. On the islands, people gather unannounced in front of a friend or family member’s house and surprise them with joyous singing. Though traditional Christmas tunes are the go-to, don’t assume that parrandas are overcome in January. The caroling often continues in the eight days following Three Kings Day, a period known as las octavitas.



Traditional food is also a key component of any Puerto Rican celebration. In December and January, you’ll often find families sharing plates of pasteles (a festive and savory tamale), pork, and arroz con gandules (a rice and pigeon peas dish). To wash it down, people in the warm-weather destination often grab a cold coquito, a drink similar to eggnog. To up the fun factor, many go on a chinchorro, which you can think of as a day of Christmas-themed bar-hopping. A group packs into a car or party bus, making several stops at different eateries and drinking spots along the chinchorro route.

You might be drawn to the islands’ resorts and beach towns as a tourist, but note that many locals leave the coasts and go to the mountains. For an authentic Christmas experience, head to the territory’s lakes and farms for a quiet getaway. You would have earned it after all the parrandas and parties.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.