The Caribbean Music Festivals That Take a Beach Vacation to the Next Level
Fun in the sun with a side of live music from icons and local talents alike.
A couple of years ago, around this time, I was emerging from a lockdown and just starting to get my feet wet again when it came to international travel. So wherever I went had to be good. I wanted to simultaneously chill out and go hard; I wanted sun and sand and blue waters, but also culture, food, and life. Preferably in summer music festival form. After a forced hiatus, I was itching to once again feel the energy of live performers and an adoring, effervescent crowd.
The 2022 St. Kitts Music Festival fit the bill. During the day I explored the island’s fortresses, rainforests, and beachside lounging, while at night into the wee hours (Caribbean festivals go hard, y’all) I caught international acts like Sean Paul, Ashanti, and Destra and local performers like Dejour and Venelle Powell. It was a little bit of sun and a lot of fun. It took multiple days of extended sleep to recover when I got back to Brooklyn, but it was worth it.
Here are four Caribbean music festivals to maximize your beach vacation this year, plus a few ideas to get you planning for 2025.
St. Kitts
June 27—29
An island of stubborn rainforest, in-your-face colonial history, defunct sugar plantations, and mischievous monkeys, it’s usually St. Kitts’ sister island Nevis, birthplace of Alexander Hamilton, that gets the shine and celebrity attention. But the larger island (government name: St. Christopher, named by Christopher Columbus after his patron saint) has a secret weapon: Since 1996, its multi-day music festival has been one of the best in the Caribbean, showcasing local performers, up-and-comers and big names from Ashanti to, yup, Kenny Rogers.
This year the festival runs three days, with headliners including Mary J Blige, Rick Ross, and Freddie Jackson, and local artists like rising star AkaiiUSweet. When you’re not listening to musicians check out the night market and satellite events like a Praise Fest, jerk chicken festival, and beachside Mardi Gras. Come for the quiet luxury, stay for the all-night ragers. Relax on black and white sandy beaches, and repeat.
Jamaica
July 19—20
Jamaica is the birthplace of reggae, so of course they’re going to have the biggest reggae festival in the Caribbean, and definitely the genre’s most culturally rich live music experience in the world. It comes from humble beginnings, starting on the streets of Montego Bay in 1993 as a vehicle for showcasing reggae and Jamaican culture. Today it’s grown to a weeklong extravaganza with arts, crafts, and food, kicking off with a beach party and including fringe events like an All White Party held on the waterfront, and a street dance.
In addition to up-and-coming local names and reggae artists like Damian Marley and Leroy Sibbles, Reggae Sumfest has hosted some heavy duty performers like Nicki Minaj and Rihanna. This year’s headliner is Babyface, who performs on July 20.
Curaçao
August 29—31
Part of the southernmost ABC islands alongside Aruba and Bonaire, Curaçao and its neighbors are known for their stunning clear waters, underwater reefs, and skinny cacti that line dramatic seaside cliffs. There’s plenty of outdoor adventure, from jet skiing, snorkeling, and spelunking in remote gorgeous caves to hiking… in remote gorgeous parks. But of the three, Curaçao is the destination for bars and nightlife. And this August, after a five-year hiatus, entertainment will once again include the Curaçao North Sea Jazz Festival, one of the hottest tickets in the Caribbean.
In the past performers have included Sting, Stevie Wonder and Bruno Mars; this year the lineup already features Gladys Knight, Marc Anthony, Seal, Jennifer Hudson, Gregory Porter, Maluma, Juan Luis Guerra 4.40, and Nile Rodgers of the band Chic (whew!). More are still being added, so stay tuned.
Dominica
October 25—27
Dominica, between Guadeloupe and Martinique, is an island you go to immerse yourself in nature. With rugged natural beauty, it’s one of the least developed in the Caribbean, with roughly two-thirds of the land covered by rainforest. After Hurricane Maria, the island made a conscious decision to rebuild with a focus on ecotourism. It now attracts outdoor adventurers for hiking, snorkeling over volcanic vents, rafting and tubing, visiting waterfalls and a pod of resident sperm whales, and sure, if you want it, laying around on the beach.
And for three nights every year those adventurers are joined by 7,000 music fans, who descend for a celebration of the island’s mixture of West African roots, Indigenous Kalinago heritage, and French and British influences. Performers span known names like Popcaan and reggae stalwarts Beres Hammond to island legends like the cadence-lypso music alive legends Midnight Groovers.
Plan your 2025 gig trip
Some of the best festivals in the Caribbean happen in the earlier months, before the weather gets too scorching. In March, the SXM Festival in St. Martin focuses on techno and underground artists (tagline: “The Island is your Dancefloor”), while for one day in April the Capella Music Festival touches down on Grand Cayman in the Cayman Islands. This year it featured artists like Richard Marx and Damian Marley—the lineup for next year has yet to be announced, but early access tickets are on sale.
The St. Lucia Jazz & Arts Festival is one of the biggest draws when it comes to island festivals and this year featured Michael Montano, Babyface, and Air Supply. It’s usually in April or May, while the newish Vujaday Music Festival in Barbados brings beats to the island with names like Diplo and Sasha. The Aruba Soul Beach Music Festival happens over Memorial Day weekend and is a banger, five days of everything from hip hop to soul to comedy, this year with Boyz II Men and none other than Mariah Carey. Set up those Google flight alerts ASAP.