5 Activities to Enjoy on a Caribbean Winter Vacation

Puerto Rico is one of the world’s best-kept secrets when it comes to winter celebrations. The season begins in late November and runs until mid-January, giving travelers a long window to enjoy the festivities.

But with so many things to do across the island, where should you start when planning the ultimate Puerto Rico vacation? How do you choose when there are so many exciting options?

Let this comprehensive guide help you. You’ll find some of the most fascinating and unforgettable celebrations across the island, each paired with hotel recommendations and insider tips to make planning easier. And if you can’t fit everyone in one trip, don’t worry – that means you can come back.

See The Nutcracker and symphony performances in San Juan

The Centro de Bellas Artes (Fine Arts Center) in the capital city of San Juan offers a full calendar of holiday-themed events throughout December, including El Cascanueces (The Nutcracker), performed by the San Juan Ballet, with live music by the Puerto Rico Children’s Symphony Orchestra. You can also see Navidad Sinfónicaa symphony orchestra concert with Christmas classics. (Pro tip: Dress for a performance – show up at the Centro de Bellas Artes in shorts, you won’t be allowed in and your ticket won’t be refunded.)

Courtesy of Discover Puerto Rico

If you enjoy shopping—especially for locally made goods—plan a ferry ride from San Juan across the bay to Cataño, where La Feria is held at the Bacardí factory. In 2024, this annual extravaganza will take place on December 7th and 8th. More than 200 Puerto Rican artisans will be selling their wares (look out for carved ones). Santos and masks made from coconut shells and local products). Food vendors serve holiday favorites and Puerto Rican classics (try CoquitoPuerto Rico’s answer to eggnog), and musicians perform live sets. The event is free and you don’t need a ticket.

Just behind Cataño, the Parque de las Ciencias is the scene of a spectacular Christmas light show. The event features 42,000 LED lights and colorful illuminated sculptures depicting Christmas scenes from around the world as well as Puerto Rico’s culture and heritage.

Courtesy of Discover Puerto Rico

For easy access to Cataño and the light show, stay at the elegant Condado Vanderbilt. (Be sure to reserve a table at their award-winning 1919 ocean-view restaurant with a Michelin-starred chef.) Or try O:lv Fifty Five, an adults-only boutique hotel with an array of unusual amenities—reserve Book one of these floating deck experiences in advance.

Attend light festivals in Yauco and Playa Combate

The holidays are one of the most wonderful times of the year in Yauco, and the annual tree lighting ceremony draws virtually the entire town to Arturo Lluberas Park in early December. If you miss it, there’s plenty more to enjoy.

Yauco is one of Puerto Rico’s most important coffee-growing regions. You can add a coffee tour to your itinerary or, if time is short, grab a coffee at Carajillo Coffee House, which serves vacation-themed drinks. If you’re traveling with children, they’ll enjoy the dedicated party area where they can write letters to Santa Claus while enjoying hot chocolate. Accommodation options include the Fox Hotel, a four-star pop art-style hotel 16 miles from Yauco.

Courtesy of Discover Puerto Rico

Additionally, in early December, more than 200 boats decorated with colorful Christmas lights float in the water just off Combate Beach, part of the Boquerón National State Forest in Cabo Rojo on the west coast of Puerto Rico. The Navideño (Christmas Festival) festival is just part of the appeal here – during the day you can experience one of Puerto Rico’s most popular beaches.

Luichy’s Seaside Hotel is located directly on Combate Beach and is therefore perfectly located for the festival. Two on-site restaurants ensure you don’t go to bed hungry.

Support local artists and artisans in Vieques

The Vieques Holiday Stroll/Paseo de Navidad on December 19, 2024 is a one-night only event organized by local artists. Shops will remain open late for gift shoppers looking for the most unique arts and crafts items to take home.

Vieques also boasts some of Puerto Rico’s most exceptional beaches (which is saying a lot for a place that has a lot of them), including Caracas and La Chiva. Additionally, the island is known for its bioluminescent bay and the waning moon on the night of the event creates perfect conditions for the night kayak tour.

El Blok and Casa Solaris at Hix Island House Hotel are both design-focused hotels in Vieques, each influenced by brutalist architecture. The latter is the island’s first solar-powered hotel to be completely disconnected from the national grid.

Attend a mask festival in Moca

The Festival de Máscaras y Parrandas (Masks and Party Festival) celebrates Puerto Rico’s long, storied mask-making tradition in Moca from December 27-30, 2024. Expect music, dancing and colorful costumes in a loud, joyful parade.

Known for its lace manufacturing, Moca is the world capital of Mundilloa type of lace that looks like ultra-fine crochet. Learn more about the long history of this craft at the Museo de Mundillo, the lace museum. The on-site shop sells locally made mundillo.

Stay at the luxurious Royal Isabela and stay in individual casitas that ensure privacy and relaxation. Some casitas offer ocean views.

Celebrate the New Year in Puerto Rico

Put on your dancing shoes and say goodbye to 2024 and hello to 2025 as you dance salsa at the Gran Bailable Fin de Año, a glittering year-end celebration on December 31, 2024 in Guayanilla. Dress is formal and tickets are required. With a VIP ticket you get dinner, unlimited drinks, table service and midnight asopaoa classic Puerto Rican stew that will help you gain strength for a few more dance lessons.

Costa Bahía hosts the Gran Bailable Fin del Año, so it makes sense to stay where the action is (and you can also stumble to your room when the music stops at 2 a.m.). A casino, billiards parlor and two swimming pools are on site. If you wake up on January 1st and need to stretch your dance-weary legs, Guayanilla offers plenty of hikes with photogenic views. The nearby Bosque Estatal de Guánica is a dry, desert-like forest overlooking the Caribbean Sea, while Finca del Girasol has sunflower fields perfect for sunny selfies.

Courtesy of Discover Puerto Rico

If you’re in the San Juan area, welcome 2025 with a celebration of family-friendly entertainment, renowned dining and more at the 45,000-square-foot Distrito T-Mobile entertainment center. Ring in the New Year in style with performances at Dick Clark’s rockin’ New Year’s Eve with Ryan Seacrest 2025presents exceptional Boricua talent.

Celebrate Epiphany in Ponce

Live music, bingo and raffles are just some of the activities at the Hilton Ponce Golf & Casino Resort’s annual Día de los Reyes Magos celebration in Ponce on January 6, 2025. That day marks the three wise men and their journey to meet the baby Jesus honored in Bethlehem.

Most events take place in the city square and at the Casa Museo de los Santos Reyes (Museum of the Holy Kings), and of course you should stay at the Hilton. Enjoy spectacular Caribbean views at this beachfront hotel, which features two outdoor pools, a 27-hole golf course, mini golf, tennis courts and more. If you arrive before January 6th, stop by the nearby town of Juana Díaz, known for its holiday honoring the Three Wise Men.

Attend a street festival in San Juan and take a food tour

Courtesy of Discover Puerto Rico

The holiday season officially ends with the lively three-day celebration called the San Sebastián Street Festival, taking place on the blue cobblestone streets of Old San Juan from January 16-19, 2025. It all begins at 5pm on the first day of the festival with a parade of life-sized papier-mâché interpretations of some of the island’s most well-known and beloved cultural and political figures. Music, food, art and of course dance – it’s all waiting for you.

Book a food tour with Spoon so you can take a break from the party and sample some of the island’s iconic dishes associated with the holidays, such as Arroz con gandules (rice with pigeon peas), Pastel colors (related to empanadas), pernil (roast pork) and coquito.

El Convento or Gallery Inn, both in Old San Juan, are just steps from the festivities. El Convento, housed in a former monastery, is steeped in history, while the Gallery Inn, founded by an artist, is unforgettable.