Despite needing time to to recover from an onslaught of hurricanes last fall, the Caribbean hosted more than 30 million tourists in 2017—a record—and it's ready for more. Consider this your cultural calendar for the region; we'd happily book a flight to attend any of the food festivals, regattas, or Hamilton performances. Book a trip that does some good. All you have to do? Show up and spend your tourist dollars.
Saborea, Puerto Rico (April 5-8)
For the eleventh year in a row, the Saborea food festival will take over San Juan in a celebration of Puerto Rico's best flavors. (Try the mofongo and pitorro cocktails.) Keep an eye out for local celebrity chef Giovanna Huyke (often referred to as the "Julia Child of Puerto Rico"). This year’s event will take place at the Balneario de Carolina in San Juan, Puerto Rico. Tickets are available online.
Antigua Sailing Week, Antigua (April 28–May 4)
Regattas come around the Caribbean often, but Antigua Sailing Week is the biggest in the region and a major event for sailing enthusiasts. Sure, there are races to compete in, but spectating is arguably just as fun. On-shore events intersect the course, and yachts for hire are available for those wanting to chase the race. Just head to Nelson’s Dockyard in St. Paul Parish in Antigua.
Crop Over Festival, Barbados (May 6–August 6)
For more than 200 years, the island of Barbados has celebrated the end of sugar cane season with two months of events leading up to a blowout parade—collectively known as the Crop Over Festival. There are food and craft fairs through June and July, leading up to the final celebration, Kadooment Day, on August 6. Reminiscent of Carnival, revelers covered in sequins and feathers lead the Kadooment Day parade through the city, with live music and moving bars in tow.
Mango and Food Festival, Nevis (July 5–8)
Within the Caribbean, the island of Nevis is known for its mangoes (more than 40 kinds!), and a burgeoning culinary scene. The Nevis Mango and Food Festival brings the two together, challenging participating chefs to incorporate mango into every dish served. The result, despite the potential for kitsch, is an offering of clever dishes—we'd try Judy Joo's mango-infused Korean food, or just about anything tying in the island's fresh seafood—from local and internationally renowned chefs.
Antigua Sailing Week.
Havana Carnival, Cuba (July 1–August 31)
Carnival is Cuba’s can’t-miss cultural event, with celebrations lasting every weekend through July and August across several cities. Santiago de Cuba is known by locals to host the country’s most riotous celebration in July, but Havana Carnival remains the largest and most popular with travelers. Head to Havana’s Malecon on the weekends to enjoy music, parades, street parties, fireworks, conga lines, and more.
Summer Festival, Anguilla (August 1–12)
Anguilla Summer Festival kicks off with a series of pre-Carnival events, leading up to the main event on August 12. Boat races and beach parties with live music are planned most days, with the pinnacle Grand Parade of Troupes on August 10.
Caribbean Sea Jazz Festival, Aruba (September 21 & 22)
The Caribbean is home to a handful of popular jazz festivals, and the Caribbean Sea Jazz Fest is a local favorite. Like many of the other Caribbean festivals, it pulls both local and international performers, with a mix of jazz, Latin, soul, and funk. Past headliners have included Crosby, Stills & Nash, and Earth, Wind & Fire.
Eat Local Restaurant Month, Aruba (October)
Throughout the entire month of October, the island of Aruba celebrates Eat Local Restaurant Month. Hop from one restaurant to another and indulge in $15 lunches and $30–$40 dinners at participating venues. Expect everything from fresh seafood to steak dinners, with a mix of international and local flavors.
Hamilton in Puerto Rico.
Caribbean Food & Wine Festival, Turks & Caicos (November)
Every first week of November the Caribbean Food & Wine Festival takes over Turks & Caicos. One of the most sophisticated food events in the Caribbean, this festival is known for bringing bold-faced names like celeb chef Melissa d'Arabian and Victor Yu to the islands for a series of meals and events that are well worth traveling for. Want to have dinner next to keynote chefs and sommeliers? Keep an eye on their site as the event nears to snag your seat at each great meal.
National Day (St. Lucy’s Day), St. Lucia (December 13)
Saint Lucia's Day, is a national holiday on the small island, set to honor the patron saint of light. This year the holiday falls on December 13, though the events really worth catching are the Christmas light and lantern displays the evening before, when lantern-making competitions are held around the island and an impressive firework show closes out the holiday.
'Hamilton', Starring Lin-Manuel Miranda, Puerto Rico (January)
We'd fly to Puerto Rico just to see Lin-Manuel Miranda back in the title role of Hamilton—this edition of the rap-sical will pay tribute to Lin-Manuel's Puerto Rican roots and Alexander Hamilton's birthplace on the nearby island of Nevis. The dates are yet to be confirmed, though we know it's being staged on University of Puerto Rico's campus, and will undoubtedly be the island’s biggest event of the year.