Flags of the United States and Puerto Rico line the Teodoro Moscoso Bridge for the annual running of the World's Best 10K Race in February. The event draws more than 13,000 international participants—from professional athletes to costumed groups to family walkers—and offers a $100,000 bonus for a new 10-kilometer world record. The route crosses over the San José Lagoon near Luis Muñoz Marín International Airport. Spectators are invited to a weekend fitness festival and a giant pasta party at the Roberto Clemente Coliseum. Shuttles run from hotels in Condado and Isla Verde; parking is available on the University of Puerto Rico campus.
Art aficionados flock to Old San Juan on the first Tuesday of the month for Gallery Nights (Noches de Galerias), when more than two dozen galleries and museums stay open late. Here's a chance to mingle and sip a glass of wine while admiring the works of top Puerto Rican artists. The series runs from February through May and September through December.
One of the most prestigious events on the island, the nearly 3-week long Casals Festival in February and March presents world-renowned orchestras, conductors and guest soloists in concert at the Luis A. Ferré Performing Arts Center. Violinist Pablo Casals, who spent the last two decades of his life in San Juan, founded this classical festival in 1957.
Now in its second decade, the Heineken Jazz Fest in March offers a four-day lineup of international stars and local favorites. This outdoor happening at the Tito Puente Amphitheatre in Hato Rey is one of the Caribbean's premier events in Latin jazz, a tropical fusion of samba, merengue and salsa rhythms.
Head to the beach on the eve of June 24, San Juan Bautista Day , to honor the island's patron saint and the capital city's namesake, St. John the Baptist. A week of religious processions and block parties commences on the night of June 23, when celebrants gather on the beach. At the stroke of midnight, everyone walks backward into the water three times—falling in at the end—to ensure good luck for the coming year. If you're not close to the ocean, the nearest swimming pool will do.
Every town has its own patron saint, and almost every weekend is dedicated to a different religious festival. A summer highlight is the Fiestas Tradicionales de Santiago Apóstol in Loíza, famous for its Afro-Caribbean food, bomba music and parades of vejigantes—brightly costumed characters in horned masks. This coastal village northeast of San Juan retains one of the highest populations of African and Taíno descendants on the island, and its 3-day carnival in mid-July is a unique blend of folk traditions.
During SoFo Culinary Fest , held in mid-August and early December, the trendy South Fortaleza district in Old San Juan becomes an open-air restaurant and music club. Streets are closed to traffic, and more than two dozen eateries set up tables and tents to show off Brazilian, French, Italian, Mediterranean, Mexican and Spanish cuisine—with a Puerto Rican edge.
One of the longest-running fishing competitions in the world, the International Billfish Tournament has been attracting deep-sea anglers to Puerto Rico since 1953. Challengers hook and release scores of Atlantic blue marlin during the week-long event in October; record catches in the waters off San Juan have tipped the scales at 1,000 pounds. The Club Náutico marina near Condado hosts the event; trophies are awarded for teams, individuals and best boat in the nautical parade.
With its plazas decorated in glittering ornaments and its Colonial buildings outlined in lights, Old San Juan is a magical place for the holidays. The season begins with the Lighting of the Christmas Tree on the Paseo de la Princesa, where families in shorts stroll beneath the twinkling branches of banyans and palms. The Ballet Concierto de Puerto Rico presents its annual Nutcracker Suite at the Luis A. Ferré Performing Arts Center, and Christmas scenes adorn the grounds of the Art Museum of Puerto Rico (Museo de Arte de Puerto Rico) and the Botanical Garden of the University of Puerto Rico (El Jardín Botánico) . Año Viejo , New Year's Eve, starts with a day of house-cleaning—out with the old, in with the new—before the big party. Some good luck traditions include sprinkling sugar outside homes, throwing a bucket of water out the window and eating 12 grapes at midnight.
While most folks are experiencing the post-holiday blues, families in Puerto Rico extend their celebrations through January 6, Three Kings Day (also known as the Feast of Epiphany). This traditional gift-giving day commemorates the arrival of the three wise men in Bethlehem bearing gold, frankincense and myrrh. On the eve of the Día de los Reyes, children put grass in a shoe box under their beds to feed the camels—and awake to find presents from the kings. Thousands line up on the holiday morning at The Fortress (La Fortaleza) to receive a gift from the governor. Games, puppet shows, music and food are all part of the festivities. Special events on the eve of Día de Los Reyes include the Concierto de Reyes (Concert of the Kings) at the Luis A. Ferré Performing Arts Center, a traditional performance by the Puerto Rican Symphony Orchestra and local children.
The holiday season officially comes to a close with the San Sebastian Street Festival in mid-January. Old San Juan's version of Mardi Gras is marked with nightly parades of masked and costumed characters, along with folkloric dances, music, traditional foods and crafts.
See all the AAA recommended events for this destination.