Insider Secrets of 3 Stunning Caribbean Islands

Rediscover Jamaica, Grand Bahama, and the Dominican Republic with a local guide.

By Kathryn O’Shea-Evans

Amid all the thronged sights in the Caribbean, there’s still buried treasure—hidden gems that locals know of but few travelers do. We asked three longtime residents of Jamaica, Grand Bahama, and the Dominican Republic to share their favorite beaches, shops, and watering holes. The result? A collection of spots where you can still find the authentic Caribbean, unspoiled by crowds.


British entrepreneur Chris Blackwell—Bob Marley’s former producer and cofounder of Blackwell Rum—knows the unofficial capital of reggae well. His go-to restaurant? “Chris’s Cook Shop (Main St., across from Maxine’s Hot Spot; 1-876-861-1611; dinner for two, $70*), in the heart of [the town] Oracabessa, has been serving Jamaican specialties for more than 16 years and is known for its curry goat,” Blackwell says. “What I love most about it is that you get to interact with the locals and really get into the vibe of the community.”

After lunch, Blackwell might catch some rays on Button Beach (St. Mary), which is hands down his favorite stretch of sand on the island. “It’s a rustic beach with calm waters in the Bay of Oracabessa with views of the mountains and fisherman’s village,” he says. “It’s perfect for a swim or taking the paddleboard out at any time of day.”

Another must-see sight? Noel Coward’s former home, Firefly (Firefly Hill Rd.; 876-725-0920; admission, $10). “It has one of the most incredible views in Jamaica of a small town called Port Mari,” Blackwell says. “It’s 1,200 feet above sea level, and on a good day you can see as far as Portland, the neighboring parish along the coast. I usually take friends or invite guests when I’m around for a rum punch to enjoy the view.”

Grand Bahama

The northernmost atoll of the Bahamas is a paradise 95 miles long and 15 miles wide. Fashion designer Theodore Elyett, who doubles as a Nassau-based reporter for EyeWitness News, has a few insider tips. “If you’re looking for the best ‘island-style’ meal, Sire’s Restaurant & Bar (Queen’s Hwy., Freeport; 242-351-1950; dinner for two, $22) is the spot,” he says. “My favorite order there is the shrimp and conch dinner, which comes with peas ’n’ rice, macaroni, and coleslaw. I would be remiss if I didn’t suggest washing that down with an ice-cold Kalik—a Bahamian beer 30 years in existence.”

Don’t miss shopping at Port Lucaya Marketplace (1 Seahorse Rd., Freeport; 242-373-8446). It’s reportedly the largest alfresco mall in the Bahamas. Elyett also recommends Gold Rock Creek Beach (Freeport) for a little R&R. “I think it’s the best beach on the island—Pirates of the Caribbean was filmed there.”

Dominican Republic

Just a two-hour flight south of Miami, this diverse Caribbean country is chockablock with great food. “Jalao (103 Calle el Conde, Santo Domingo; 809-689-9509; site in Spanish; dinner for two, $42) is one of my favorite local restaurants,” says resident Keilyn Fondeur, the jewelry designer behind Topacio, whose signature pieces often use local amber and larimar stones. Jalao is in Colonial City, Santo Domingo—a neighborhood she calls “magical” and “heritage-rich.” “The atmosphere is very colorful, very Dominican. I really like the mofongo [a plantain and shrimp dish]—I’d go back just for that!—the little ribs, and the goat croquettes. The beer is served super cold.”

While sites such as 16th-century Catedral Primada de América (Callejón de los Curas, Santo Domingo; 809-682-3848; admission, 46 cents) and the 1502 Fortaleza Ozama (1 Calle las Damas, Santo Domingo; 809-688-1553; admission, 54 cents) are among Fondeur’s recommendations, she really raves about the beaches. “Coson Beach [in the Las Terrenas neighborhood] is one of the liveliest, where you can find ample varieties of restaurants and bars,” she says. “Its crystal clear waters make for a perfect place to spend a day.”

  • *Prices have been converted to U.S. dollars. Estimated meal prices do not include drinks, tax, or tip.
  • NOTE: Information may have changed since publication. Please confirm key details before planning your trip.
  • Published: November 2018