The 500-year history of Puerto Rico has created a rich and diverse cultural heritage, which is celebrated in the many festivals held year-round on this enchanting Caribbean island. A round-up of some of the most popular festivals may help you decide when to plan your trip for the highest fun quotient.

Le Lo Lai is an ongoing cultural program that occurs every week of the year, and has been going strong for more than three decades. It was created to foster Puerto Rican culture and music through performances that showcase the local Spanish, African and Taino Indian heritages. Locals and visitors alike attend Le Lo Lai shows to enjoy and learn about the music and folkloric dancing. Le Lo Lai performances can be found at San Cristobal Fort on Tuesdays at 6:00 PM ($3.00), Plaza Darsenas on Fridays at 8:00 PM (free), and Plaza Ventana al Mar on Saturdays at 8:00 PM (free).

Each year on November 19, Puerto Ricans celebrate Discovery of Puerto Rico Day, commemorating the landing of Christopher Columbus during his second voyage to the New World. A huge parade lines the main streets of San Juan, and practically everyone is off work and school to celebrate. Visitors should expect to enjoy much fanfare including dancing, music, games, competitions, parades and, of course, lots of local cuisine.

Three Kings Day is an incredible Christmas season celebration that is a must if you are lucky enough to visit Puerto Rico during this time. Here, as in much of the Latin world, Santa Claus is eschewed in favor of the Three Kings, who rule the yuletide. Although December 25 is celebrated, the most important day is January 6, El Dia de los Tres Reyes Magos—the day that the Three Kings arrive. Children gather grass to place at the foot of their beds on that night, so the kings’ camels will have something to eat. The day is celebrated all over the island, but nowhere is it more exuberant than in the small town of Juana Diaz, whose Three Kings parade through the entire island. Jody Diamond, president of Diamond PR in Miami and frequent traveler to Puerto Rico, counts Three Kings Day as her favorite Caribbean holiday. “There is nothing more beautiful than San Juan at Christmas,” she says. “Trading a Christmas tree for a Palm tree has its benefits.”

Later in January, the San Sebastian Street Festival brings the cobblestones of Old San Juan to life in a vibrant street party. For more than 50 years, artists and crafters have exhibited their work as thousands of locals and tourists fill the streets to browse the vendors. Music and plenty of food round out the event, which is topped off with an energetic parade of people in costumes and masks.

The Ponce Carnival is Puerto Rico’s version of Mardi Gras, and one of the oldest festivals on the island, dating back to the 1700s. Over the week leading up to Ash Wednesday, this colorful celebration takes place, with costumed vejigantes taking to the streets with their vivid demon masks amid hordes of masked revelers and thumping bomba music. The Ponce Carnival ends on the eve of Ash Wednesday with the Entierro de la Sardina—the mock “Burial of the Sardine” funeral procession that is delightfully offbeat, led by drag queens and fake mourners. It’s all a great, oddball party.

The Casals Festival is held in late February through March, and is one of the world’s most prestigious festivals of classical music. Internationally-renowned artists converge for three weeks to bring a top-notch level of artistic offerings to Puerto Rico, including pianists, chamber musicians, violinists, and opera singers.

As we enjoy the last of blissful sunny days, cookouts, and playing in the sand, we want you to share a photo of your Favorite Beach Vacation with us. You might win a free $250 (USD) Visa gift card which you can use for any upcoming travel plans you might have. Click here to learn how to enter.

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Image 1 – Street Carnival
Photo courtesy of Puerto Rico Tourism Bureau

Image 2 – Traditional Dancer
Photo courtesy of Puerto Rico Tourism Bureau