May – various municipalities
La Campechada brings together artists, performers, musicians, actors, puppeteers, and others with the aim of educating the public about Puerto Rican art and culture. Every year the festival is dedicated to a prominent Puerto Rican artist and that becomes the inspiration for many of the new works presented during the festivities. There is an Artisan Fair, a Book Fair, an Art Fair, guided walks, conferences, workshops, live drawing, theatrical performances, and more. The city hosting the event changes each year and in 2019 La Campechada will be held in Ponce.
Festival de la Piña Paradisíaca
May or June – La Parguera, Lajas
The Pineapple Festival is celebrated every year in La Parguera, an oceanfront community in the southern town of Lajas. The festival features vendors selling locally grown pineapples and dozens of local agricultural products and fried foods while local bands liven up the evening. La Parguera is packed with restaurants and bars as well as small hotels, charter boat rentals, and even a bioluminescent bay. During the celebration there is a 5K race with an impressive view of the marina and mangrove coves that make La Parguera a favorite getaway for both locals and tourists.
Noche de San Juan
June 23rd – San Juan
Saint John's Eve, locally known as Noche de San Juan, is an unofficial celebration in the capital of Puerto Rico that celebrates the nativity of Saint John the Baptist. Hundreds of people crowd the beaches so that at midnight they can jump backwards into the ocean seven times for good luck. Some hotels and bars also throw parties in honor of Noche de San Juan.
Festival de Santiago Apóstol
Last weekend of July – Loíza
In Loíza, there is another style of vejigante, the ones whose masks are made from coconut and drift wood. During the Festival of Saint James, the Apostle, in Spanish Santiago Apóstol, there is a lively parade through the town where the vejigantes and the Spanish knights do battle, representing the struggle between the forces of good and evil. Bomba music, a traditional folk music with a distinctive African influence, thumps out while dancers use their colorful skirts to create a dialogue with the drummers, and the musicians respond to the dancers rather than the other way around.
Festival Nacional Indígena
End of November – Jayuya
This festival celebrates Puerto Rico's indigenous roots and the influence of Taíno culture and traditions. The town of Jayuya was named after one of the big caciques, or chiefs, that lived on the island when the Spanish arrived in the 1500s and where Taíno hieroglyphs were found carved into a giant boulder. The Taínos were eradicated by the Spanish but their influence is still present in Puerto Rican culture. Jayuya also contains the highest peak in Puerto Rico, some of the best coffee plantations on the island, a moonshine distillery, and a hot air balloon. Getting there is tricky but worth the trip!
December 24th – all over the island
During Christmas Eve, known as Nochebuena, people gather with their families and friends to eat lechón and arroz con gandules (roast pork and rice with pigeon peas), drink coquito (like eggnog but coconut-based), and sing trullas (Christmas songs usually accompanied by drums, maracas, and güiros). If you're a visitor to the island, most tourism services will be operating on the 24th, and in the evening many hotels and restaurants offer special Christmas dinners.