The party doesn’t end at the beach. When visiting any Caribbean island, travelers are usually enamored by its blue waters and warm rays of sunshine. But to really experience the fullness of the culture, you have to leave your resort and see the attractions.
One of the best ways to do this is through one of the most celebrated exports of the region — music. From pioneers like Bob Marley to contemporary acts ranging from Sean Paul to Popcaan, the music of the islands has garnered fans from far and wide.
If you can’t catch some of your favorite acts stateside, seeing them onstage in the Caribbean is a different experience — the energetic crowds, the scent of spices lingering in the air from local food stalls, and, of course, the sound of your favorite soca, dancehall or reggae song playing until the sun comes up, and maybe even after that. It’s OK because you can sleep it off on the beach.
So, consider one of these festivals when building your itinerary for your next island getaway.
Jamaica
Rebel Salute
Jamaica offers numerous music performances around Christmas and New Year’s Eve, but one of its most notable is Rebel Salute, held every January.
The music festival in Ocho Rios celebrates the contributions of reggae music to Jamaica. It also includes a cannabis symposium called Herb Curb with local vendors and an ital (the diet of the Rastafarian movement) food village consisting of only vegetarian and seafood options to adhere to its strict no-meat and no-alcohol policy.
Billed as the “the people’s festival” started by reggae promoter and prominent DJ Tony Rebel, the festival’s 30th anniversary at the Plantation Cove venue in January 2024 featured 30 acts, including notable artists like Sean Paul, Capleton, Luciano and Anthony B.
Reggae Sumfest
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In the summertime, a weeklong party accompanies Reggae Sumfest in Montego Bay (July 14-20). Beyond the numerous concerts, promoters also host beach parties and after-parties, so you will have more than enough to keep you entertained. The event is one of the island’s biggest, with performances dating back to 1993.
Make sure you arrange a driver ahead of time with your resort or hotel; there are no ride-hailing services. Most attractions and shops are spread out in Jamaica.
Where to stay: In Ocho Rios, the new Sandals Dunn’s River (rooms start at $391 per person, per night) is near other attractions within the island’s tourist village. In Montego Bay, you have a lot more accommodation options, but a great bet is the centrally located Half Moon (rooms start at $487 or roughly 48,000 American Express Membership Rewards points per night).
Related: The best all-inclusive resorts in Jamaica, from honeymoon hot spots to family-friendly resorts
Trinidad and Tobago
Trinidad Carnival
There’s no celebration quite like Carnival. The biggest party in the Caribbean begins in early February with Trinidad’s annual cultural extravaganza. While it’s not necessarily a music festival, it includes a series of concerts from superstars in the soca music world.
You can party and dance all night long for the week leading up to Jouvert and then put on your costume to join the mas parade. As a world-famous event that draws big international crowds, planning early is important if you want to secure a flight and hotel.
Leading up to mas, there are events known as “fetes,” or parties tied to different bands like Exousia Mas and Bliss Carnival, who form part of the main event. The bands are also where you will secure your mas costumes, and participants usually register well in advance to snag their favorite look.
Consider booking arrangements with an experienced tour company like Carnival Jumpers to make your life easier, especially if it’s your first time.
Trinidad’s sister island, Tobago, also has its own Carnival celebration in October with Tobago Carnival (Oct. 25-27).
St. Lucia
St. Lucia Jazz & Arts Festival
You may not think of jazz as island music, but the region has a long-standing relationship with the genre, giving it a vibrant spin. The St. Lucia Jazz & Arts Festival (April 30-May 12) is the oldest in the Caribbean, dating to 1991, and is held every year from late April through early May.
The event draws a mix of international and local artists to highlight an array of musical genres, from zouk to gospel and pop. This year, the festival will feature headline acts like Davido, Machel Montano, Samara Joy, Beres Hammond, Jon Secada and Chloe Bailey.
Related: The 22 best Caribbean resorts, from boutique literary haunts to exclusive private-island escapes
If you’re visiting for the concerts, it’s also a great chance to take in the island’s art scene. St Lucia’s lush landscapes and views of the iconic Piton mountains have served as the muse for many in the local art community.
You can immerse yourself even further by staying at Anse Chastanet (rooms start at $780 per night) — a luxury 49-room boutique hotel boasting gorgeous views of the Pitons — and taking one of its locally-led immersive art classes.
Related: 19 relaxing adults-only, all-inclusive resorts for a kid-free vacation
Outside of music, the jazz festival also has an art component. You’ll find events like culinary experiences in Sculpture Park (free of charge).
Barbados
Crop Over
In Barbados, there’s no bigger party than Crop Over (July 31-Aug. 9), a cultural celebration that dates to the 1780s and is tied to sugar cane plantations during slavery.
The weeklong celebration is filled with events for all ages, including energetic fetes and mimosa brunches that will have you on your feet all day and night. The goal is to make it all the way to the finale, Kadooment Day, which is what Bajans call their mas parade.
Like the Trinidad celebration, this is another event you should consider booking with a group if it’s your first time. Your itinerary will be mostly based on the band you choose, like the Aura Experience — one of the largest and best known for Rihanna’s iconic Crop Over appearances.
And you can’t leave the island without going to at least one fish fry or tasting a Gap Burger — an iconic Bajan street food staple. In addition to nonstop fetes, there are a number of concerts featuring the best in soca, ranging from Alison Hinds to Destra.
Barbados Reggae Festival
Outside of the Crop Over celebrations, one of the biggest parties of the year is the Barbados Reggae Festival (April 23 -27) in Farley Hill National Park, which occurs in April each year and attracts international artists within the genre.
Dominica
World Creole Music Festival
The lush green landscapes of Dominica have garnered a lot of attention over the last few years. With its rich biodiversity and cascading waterfalls, Dominica beckons nature-loving travelers keen to soak up the island’s beauty on a scenic hike or to set sail and admire views from the water.
But it’s the World Creole Music Festival that attracts music lovers to the island in the fall. Every October, the event hosts an array of Caribbean and international artists to celebrate Creole music and traditions in the capital city of Roseau. Roseau is also the cultural hub of the island; a great place to learn about the island’s history is the Dominica Museum.
Jazz ‘N Creole Festival
If your travel plans are in the spring, the Jazz ‘N Creole Festival (May 5) held every May in Portsmouth is a must for your itinerary. The festival is filled with fusion performances mixing jazz elements with Creole sounds for a unique experience.
Portsmouth is close to Cabrits National Park, where you can hike one of its trails and understand why they call this the Nature Island.
Related: 9 Caribbean resorts, from Barbados to Belize, you need to visit
There’s no shortage of luxury accommodations, including Secret Bay (rooms start at $1,270 per night), which is home to just 10 sustainable villas; visitors can immersive themselves in the jungle around them while not losing out on the lavish service.
The more affordable eco-conscious 151-room InterContinental Dominica Cabrits Resort & Spa (rooms start at $482 or 60,000 IHG points per night) offers visitors “blissful seclusion” right on the beach.
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