Written by Ellen Honey
January 2020

The tropical climate and peaceful beaches of the Caribbean provide a perfect setting to lime the day away listening to the rhythm of the islands. The music is a fusion of African, European and indigenous influences. Each European power influenced the culture and music of its respective island, but all the rhythms are heavily inspired by music brought over by African slaves. Whether you want to relax with authentic island tunes or give in to a reggae beat, these music venues are guaranteed to lift your spirits during a Caribbean getaway.

Atlantis Paradise Island, Nassau, Bahamas

Bimini Road, featuring authentic Bahamian cuisine and entertainment against a backdrop of colorful junkanoo decor, sits in the center of Marina Village. Bimini Road provides a total Bahamian experience — from the savory local cuisine to the high-energy live music. Just-shelled conch is cooked to order in the open kitchen’s conch station. The plaza in front of the restaurant comes alive in the evening with local musicians and spirited junkanoo dancers.

Where to Dock: Atlantis Marina

Governor’s Harbour, Eleuthera, Bahamas

Pineapple Fields Resort in the Bahamas Out Islands is home to Tippy’s, a rustic, bright yellow, blue-trimmed building. On Saturday night, fans head to Tippy’s to hear Black Belly & the Haitian Sensations, Eleuthera’s best “Rake and Scrape” band. Fresh local produce and seafood dictates choices on the chalkboard menu called “some of Eleuthera’s best food” by Bon Appétit.

Where to Dock: French Leave Marina

Havana, Cuba

Visitors to Cuba must experience the spectacular show of music, dance, feathers and sequins at the legendary Tropicana Club, one of the world’s most beautiful and famous cabarets. Begin the experience with champagne or try one of the menu’s national or international drinks made from seductive Cuban rum. Famous people from around the world sit in the audience or, like Josephine Baker and Xavier Cugat, have performed here. Knowledgeable travelers suggest booking in advance.

Where to Dock: Marina Hemingway Cuba

Negril, Jamaica

Seven Mile Beach’s best spot for live reggae and mingling with locals is Bourbon Beach, Negril’s party capital. Known for jerk chicken and upbeat entertainment, the venue has hosted genre greats such as John Holt and Gregory Isaacs. The property has live music or a DJ seven nights a week. Saturday is dancehall night; up and coming talent appears on Thursdays. The festive bar is open daily serving jerk, signature shakes and a memorable bourbon experience.

Puerto Plata, Dominican Republic

Along the western side of the Malecón, a 22,200 square foot outdoor Grecian amphitheater faces the Atlantic Ocean. The San Felipe Fort lies on one side and lush La Puntilla park is on the other. With a capacity of more than 4,000 spectators, La Puntilla is perfect for concerts, dance performances, and other artistic events featuring Dominican and international artists.

Where to Dock: Ocean World Marina

San Juan, Puerto Rico

With stars overhead, audiences enjoy a variety of music genres including reggae, Spanish pop and hot Latin jazz accompanied by the rustling leaves of nearby trees. The open-air arena is named after the late mambo musician and percussionist, Tito Puente, who is widely credited with introducing the Cuban-style big band sound to the world. Considered the king of Latin music and of the timbales, he is best remembered for his dance-oriented mambo and Latin jazz compositions. He appeared in several films that also featured his music including “The Mambo Kings.”

Where to Dock: San Juan Bay Marina

St. Thomas, U.S. Virgin Islands

Bolongo Bay, with its golden beach and spectacular Caribbean views, is the temporary post-hurricane home for Iggies Oasis, a two-story poolside “pop-up” with a full menu spiced with local ingredients and live entertainment. Check out the dates for Iggies’ weekly Carnival Night Extravaganza with limbo show, live steel pan Calypso, Mocko Jumbie dancers and more. Cool cocktails feature five flavors of U.S. Virgin Island Cruzan rum. Settle into a comfy beach chair beside rustling palms and strolling iguanas, order a bucket of Iggies Voodoo juice, and let the island vibe flow!

Where to Dock: Marina at Yacht Haven Grande

The Valley, Anguilla

Bankie Banx’s laid-back wooden beach bar ambles across Rendezvous Bay’s pristine white sand. The detritus of island life — shipwrecked boats, mangled coconut trees, bleached-out driftwood — fuses into a blend of ultimate cool. The interior is peppered with trinkets and treasures from around the world. The Bankie Banx sound is a bit of Marley meets Dylan — a musical blend of folk, reggae, R&B and jazz. Music rides the breeze almost daily at the Dune Preserve, and on Sundays it’s live music from noon to sunset with Bankie and friends. No wonder CNN voted it the world’s #1 beach bar!

Rodney Bay, Saint Lucia

Serene beaches and undisturbed forests create a natural wonderland on this 44-acre preserve. Under the Saint Lucian government’s care, Pigeon Island has flourished into a history museum of sorts, alive with nature. Get a history lesson about previous residents (including a pirate with a wooden leg), explore the two beaches or attend a concert featuring international stars such as UB40 or Elton John. The park hosts the Saint Lucia Jazz Festival, which incorporates the Roots & Soul Festival (reggae) and the Saint Lucia Carnival in July.

Where to Dock: Rodney Bay Marina

ColeBay, St. Maarten

Visitors quickly understand why Pete’s was awarded best live music nightly on the island. It’s always busy at Pete’s Village, renowned for fun, food and great service. Adjacent to the restaurant is Pete’s Sports Bar, an entertainment area with five pool tables, dart boards and arcade games. Drop into Pete’s Corner Shop for t-shirts, handcrafted jewelry, local rum and great memorabilia. The lagoon’s waterfront has a generous dinghy dock for visiting boaters.

Where to Dock: Simpson Bay Resort & Marina

Frigate Bay, St. Kitts

Just try to resist a place that promotes itself with slogans such as “Time well wasted. Grown folks’ style.” Hang out, sip a rum punch and let the Caribbean work its magic. At sunset, lanterns atop the battered picnic tables on the sand create an instant party mood. On bonfire nights, bands hook up the generator and jam. The Royalties, the regular house band, and an occasional visit from Binkie Banx, make this spirited shack popular with locals and tourists.

Where to Dock: The Marina at Christophe Harbour


Paradera, Aruba

Casibari Rock Formations inexplicably rise from the desert in unusual configurations. It’s a unique background for Casibari Café, which began by providing thirsty, camera-toting tourists a place to grab a drink and mementos. Adding local bands and live music events has transformed the cafe into a lively nocturnal spot. The schedule is filled with reggae festivals, salsa nights and jam sessions with local musicians. At dark, the lighted rock formations create their own dramatic scene. Casibari Cafe offers an authentic Aruban experience with subtle Dutch flavors.

Where to Dock: Renaissance Marina


The Caribbean archipelago, a magnificent 2,500-mile island chain, provides spectacular ambience for music festivals. Among the earliest was Jamaica’s Reggae Sunsplash that drew visitors during the off season. Today, festivals are held year-round throughout the islands in outdoor locations ranging from intimate, rustic bungalows to massive open-air amphitheaters. Some of our favorites include:

SXM Festival
St. Maarten
March 11-15, 2020

Moonsplash Music Festival
The Dune Preserve, Anguilla
March 12-15, 2020

Vujaday Music Festival
April 1-5, 2020

Saint Lucia Jazz Festival
Pigeon Island National Park,
Rodney Bay, Saint Lucia
May 1-10, 2020

Aruba Soul Beach Music Festival
Harbor Square Marina, Aruba
May 21-25, 2020

Reggae Sumfest
Montego Bay, Jamaica
July 12-18, 2020

Dominican Republic Jazz Festival
Playa Alicia, Sosua, Puerto Plata
November 2 & 3, 2020