The 4 Best Annual Music Festivals in the Caribbean

Reggae Sumfest

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Since 1993, Jamaica’s Reggae Sumfest has grown to become the biggest music festival in the Caribbean, attracting both international artists and, of course, many of Jamaica’s very best from the world of reggae and dancehall. Kanye West, Sean Paul, Damian Marley, Ziggy Marley, Rhianna…the list of performers that have graced these stages goes on and on. This year’s Reggae Sumfest will be held July 18-23 in Montego Bay.

What to Expect

After a virtual “Taste of Sumfest” in 2020 and a 2021 postponement, expect 2022’s Sumfest to be back in full force. This year’s artists include Beenie Man, Sizzla, Bounty Killer, Shenssea, Spice, and much more. The vibe will likely be high energy, with lots of modern, bass-thumping dancehall on the big stage on the Friday night and more roots reggae on the Saturday night. Fans of 90s dancehall will especially appreciate the Saturday night lineup, which features a tribute to Madhouse producer Dave Kelley featuring some of the biggest acts of the era. There are also tons of great parties that whole week, including a free Street Dance party on the 18th, the All-White party at Pier 1 on the 19th, the Blitz Party on Tropical Bliss Beach on the 20th, and the Global Sound Clash on the 21st. 

Villas to Stay

Rental Escapes has no shortage of beautiful Montego Bay villas that would make perfect jump off points to experience the best of Sumfest. Endless Summer in the Half Moon Tennis & Beach Club will give you plenty of space as it fits up to 14 in a turreted mansion with amazing views of the Caribbean Sea, and it features an immaculate interior with hand-cut marble floors and finishes, as well as Bose speakers all throughout the villa. If you’re looking for something a little smaller, Serenity on the Beach in the Tryall Club fits up to 8 guests and is located directly on the beach, making it one of the most requested and best-reviewed villas in Montego Bay, while Windsong Villa in Round Hill stands out as a great value. All are fully-staffed, with impeccable service and top-end private chefs.

St. Kitts Music Festival

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Since 1996, the St. Kitts Music Festival has featured a variety of Caribbean and international acts in genres like reggae, dancehall, R&B, hip-hop, pop, and more. Past artists include big names like John Legend, Lauryn Hill, Patti Labelle, Ja Rule and more. This year’s festival takes place June 23rd-Saturday 25th. 

What to Expect

As with previous years, expect lots of variety at this year’s St. Kitt’s Music Festival, with a focus on both Caribbean and international music. This year’s festival features a star-studded lineup that includes Ashanti, Wale, and Sean Paul on Friday the 24th and the Keyshia Cole, Bare Hammond, and ROTIMI on the 25th. Aside from the big names, the festival also highlights a lot of local artists from genres as varied as Gospel, Zouk, Meringue, Soul Jazz, and more. The festival’s oceanside location is also a definite highlight. And while the festival itself definitely takes center stage, there are a number of beach, boat, and after parties going on all week long. 

Villas to Stay

The Four Seasons on Nevis features beautiful villas and outstanding service, and is just a short ferry ride away from St. Kitts. Standouts include Serenity Grove, which makes for a lovely retreat for up to 6 people, and Bismarkia, which features great views of the island’s lush green mountains.

Soul Beach Music Festival

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Every Memorial Day since 2000, the Soul Beach Festival has served up some of the best in soul and rhythm and blues in Aruba’s capital, Oranjestad. The five-day festival includes performances at the Soul Beach Amphitheatre, the Hard Rock Café Aruba, and the Havana Beach Club, and past performers include Alicia Keys, John Legend, Usher, Miguel, the Isley Brothers and more. This year’s Soul Fest takes place from May 25th-30th.

What to Expect

It’s the 20th anniversary of the festival after being cancelled in 2020 and 2021, so expect a proud return to form and a celebration of the festival’s history. This year sees long-time headliner Mary J. Blige return on Saturday the 28th to headline along with Kevin Ross, while the 29th is led by New Edition and Ari Lennox. Friday the 27th also features a comedy concert featuring Mike Epps, Chase Anthony, and Chris Spencer. There are also plenty of parties before, during, and after the concerts, including day parties at MooMba Beach (Palm Beach) and after parties every night. 

Villas to Stay

Majestic Retreat in Noord, Aruba is a lovely retreat that can comfortably accommodate up to 14 people and features a large open pool area, a private tennis court, and nice touches like colored glass doors. If you’re looking to stay even closer to the action, Panoramic Views is a stylish penthouse located in Eagle Beach featuring unbeatable views for up to 4 guests. 

SXM Festival

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Since 2016, the SXM Festival has brought some of the best house and techno DJs to Saint Martin for some of the best parties in the Caribbean. The lineups have been huge every year, and while there are certainly standout names like Richie Hawtin, Skream, Nina Kraviz, Maceo Plex, Loco Dice, and Dubfire, there’s also a ton of lesser-known DJs from around the world to discover. With a focus on creating smaller, more intimate experiences, SXM Festival is geared towards the more discerning electronic music fan. While this year’s festival took place from March 9th-13th, you can still get on the waitlist now for 2023.

What to Expect

While 2023’s lineup has not been announced yet, you can expect to find some big names and a deep bench in terms of DJ variety. The festival goes from day to night, so whether you like to get down on the beach or prefer more of a nighttime vibe (or both), there’ll always be a party for you to get to. The music in general is a bit more refined than your typical big-room EDM, so expect a crowd that’s a bit more sophisticated than your typical electronic music festival, and there’s a big focus on maintaining a cool, positive vibe throughout. Expect plenty of cool art installations, colorful costumes, bright lights, and world-class DJs playing intricate sets at multiple stages and venues.

Where to Stay

St Martin is one of our most popular destinations, so Rental Escapes has no shortage of beautiful Saint Martin villas that are perfect for SXM. SXM festival is concentrated around Happy Bay on the French side of the island, making the beachfront Petit Plage 5 in Anse Marcel an ideal hub to experience the best of the festival, while still being secluded enough to enjoy some much-needed rest. If you’re looking for something a bit smaller, Casa Branca, also in Anse Marcel, is perfect for up to 6 guests. And if want the ultimate in luxury, La Reve in Terres Basses is a 7-bedroom beachfront villa that really needs to be seen to be believed. 

Where to Stay While Attending a Music Festival in the Caribbean?

A private villa is ideal for any Caribbean music festival. It gives you the peace you want after partying all day or night, as well as the privacy to have your own pre-party or after party. No matter your style or which festival appeals to you most, a Rental Escapes reservations specialist will be happy to present you the best Caribbean villas for your trip, while our concierge will be happy to help arrange staff, pre-stocking, tickets, transportation, and anything else you may need. Contact us today to begin planning your Caribbean music festival experience!