Colonial Architecture on Bay Street in Harbour Island's Dunmore Town / Photography Lucy Hewett

There are 700 islands in the Bahamas, the most charming of which just might be Harbour Island, a tiny, 3.5-mile-long strip of land with pink sand beaches facing the breezy Atlantic and the quaint village of Dunmore Town tucked along a harbor. The settlement got its name from Lord Dunmore, a British loyalist and former governor of Virginia who was exiled on the island after America’s Revolutionary War. Today, colorful colonial buildings with flower gardens and picket fences line the streets, and you can walk anywhere. But don’t be fooled by the place’s quiet demeanor. Harbour Island pulls in jet-setters such as Naomi Campbell and Mick Jagger with excellent cuisine, luxe refinement and the turquoise waters it shares with Eleuthera, just across a small channel. The more rural Eleuthera, too, has a distinctive blend of natural beauty and luxury. Lenny Kravitz has a home there and hidden beaches and high-end resorts dot its shoreline. Here, five island locals share with us what they love most about their beautiful home.

Tracy Barry
Cosmopolitan Authenticity in Dunmore Town

“Harbour Island is a feeling,” says Tracy Barry, owner of the atmospheric The Landing hotel. “It’s not necessarily the same for everyone, but whatever that feeling is, it keeps you coming back.” In her 25 years operating The Landing, Barry has greeted repeat clients season a1ter season. “People who travel all over the world tell me they never go back to the same place twice, except for Harbour Island. This is an incredible place of intimacy. People are so often cut off from that in their regular lives, but here you so often and open yourself up.”

Occupying a cluster of colonial structures on Bay Street in Dunmore Town, overlooking the harbor, The Landing is an oasis of charm. Barry and her mother, Brenda—a onetime model who was the inspiration for the hotel’s signature Afro Head logo—purchased the property, then a private residence, to create a boutique experience blending Bahamian authenticity with a sophisticated, well-traveled cosmopolitanism. “Most of the properties on the island are owned by foreigners,” says Barry, who was born here but grew up in Australia and lived in New York before returning in 1995. “So it was pretty wonderful for Bahamians to own it, but also to have had the opportunity to move internationally and have a sense of what we like when we travel and blend the two.”

Decorated by designer India Hicks and her partner, David Flint Wood, each of The Landing’s 13 rooms—from a romantic third- floor attic tucked under the eaves to a standalone cottage—features mahogany four-poster beds, hardwood floors and tropical prints. Many enjoy private verandas. The traditional yet luxe aesthetic continues in a library filled with English novels, a cozy bar offering The Landing’s bespoke rum and ginger vodka, and the scarlet-walled dining room, where for 15 years Bahamian chef Madelene Pedican has been delighting longtime patrons with her goat-cheese ravioli with poached shrimp and tea-soaked raisins, and stone-crab stacks with crisp wontons. Barry says the restaurant used to try to alter the menu occasionally, but realized it was a hopeless effort: “Food is a huge memory, and people dream all year about coming back and having that same meal. Those of us who are here all the time were excited about culinary changes, but people were horrified and devastated. So we stopped.”

Consistency is also a hallmark of Barry’s other favorite food destinations around town, such as Brian’s Grill, open only Thursday to Saturday and renowned for its delectable barbecue ribs and chicken, smothered in a spicy jerk sauce. “He has all the fabulous Bahamian super-starchy sides— macaroni and cheese, peas and rice. Go to the beach with a take- away box.” Overlooking the Atlantic and serving only lunch, Sip Sip (a local word for “gossip”) is another favorite, with famous lobster quesadillas and ginger margaritas, while The Dunmore—a hotel featuring a 1960s “beach-chic vibe” by designer Amanda Lindroth—is “lovely” for its signature cocktail, the Rum Dum, incorporating egg whites and lemon and lime juice.

In addition to its gustatory pleasures, Harbour Island provides a highly curated retail experience. “We have very well-heeled travelers,” Barry says, “so shop owners have to be clever and offer great lines that often aren’t carried on this side of the world.” Blue Rooster, operated by Gabrielle Kenedy, opened around the time The Landing did. “She has an incredible sense of style, with a broad collection of caftans, sunglasses and beautiful blouses.” Hicks’ Sugar Mill boutique commissions exclusive collections from well-known designers, “which is obviously a special treat.” Barry also praises local designer Stephanie Haede Dorsett, whom we profile later in the story.

Her boutique, Shine, features her holiday-friendly dresses and jewelry, as well as housewares from Morocco: “It’s a jewel box of a store—very individual.”

After dark, Daddy D’s nightclub, operated by Devon Sawyer, is an island mainstay: “He has all of the corny and fabulous things, like karaoke nights, and a New Year’s Eve party that everyone is desperate to get into. It’s a great night out, literally for the whole family. You will see the mother, father, their children, even the grandparents.” At evening’s end, revelers repair to the Vic-Hum Club, established in 1955. “It’s a juxtaposition of fancy people and locals,” Barry says. “You go in and there might be Mick Jagger or Naomi Campbell, completely accessible to everybody. People do hyperventilate at first but they don’t disturb them. Everybody respects everyone’s space.”

Ben Simmons
Freedom and Relaxation on Eleuthera
Resort Owner

The name Eleuthera translates to “freedom” in Greek. “It’s the idea that you are free to explore,” says Ben Simmons, owner of The Other Side resort on Eleuthera and The Ocean View Club on Harbour Island. “You’re unburdened by the constraints and pressure of life. It also has to do with nature and the geography of the island—it’s spread out.” Simmons explains that Eleuthera was settled in the 1640s by shipwrecked Puritans who were seeking religious freedom. “That’s how the island got its name.”

These days, Simmons is pursuing a different kind of purity, what he describes as living in harmony with the natural environment. This was the inspiration behind The Other Side, a 30-acre off-grid glamping destination on a remote beach in Eleuthera. Constructed of crisp, white canvas and lacquered wood, seven elevated tents and three grander hilltop “shacks” are low-impact without sacrificing character or comfort, and can be completely disassembled during hurricane season. Simmons modifies the resort’s daily menu based on the temperature of the day—if it’s hot they’re serving chilled tomato soups and herbaceous salads; when it’s chilly, rich seafood and hearty vegetable stews—but he always utilizes ingredients pulled from the ocean and the adjoining organic vegetable garden.

Simmons lives with his wife, Charlotte, and their two children on the same piece of property, and appreciates the balance that this isolated stretch of coastline offers. “We wanted to celebrate the proximity to Harbour Island while not being in the middle of it,” he says. A Harbour Island native, Simmons took over The Ocean View Club six years ago after his mother, Pip, retired. “Pip’s Place,” as it’s still affectionately called, is a Caribbean institution. Its tattered luxury and laissez-faire ethos made the 14-room boutique hotel a top destination for the fashion set, and Simmons has distinct childhood memories of running around Pink Sand Beach with his inflatable toys while supermodels such as Cindy Crawford posed for pictures.

Whether on Eleuthera or Harbour Island, part of the excitement of the guest experience is choosing one’s own adventure. Less than a mile off of Pink Sand Beach, the ocean drops to over 1,000 feet deep, providing some world-class conditions for sportfishing. For a more passive experience on the water, there’s a slew of deserted beaches that can be reached by guided boat and are great for a picnic of fresh fish stuffed with vegetables and herbs.

Simmons’ days follow a familiar rhythm. In the mornings he’ll surf or kiteboard at Surfer’s Beach on the Atlantic side of Eleuthera, near Gregory Town. If it’s a calm day, he’ll cross over to the lee side to paddleboard turquoise waters over patch reef below. “On any given day, I’m out on the water on a board of some kind,” he says.

Lunch for the Simmons family usually is a salad of handpicked herbs and vegetables from the garden with snapper fillet caught off the dock by their son, Beau. But when venturing out to grab an afternoon bite, Simmons often hits Harbour Island’s Queen Conch for a refreshing conch salad. “Down-home, honest, to the point—it’s everyone’s go-to spot,” he says. “Conch, tomatoes, onions, celery, lots of lemon, lots of salt.” Or else he’s next door at Wade’s Takeaway, another classic Bahamian haunt. “He does the best fried fish with excellent peas and rice.”

Though he might prefer the quiet life on Eleuthera, Simmons is no stranger to an enchanting night out on Harbour Island. “People are always surprised by how good the food scene is there.” Recently, he’s been starting with an aperitif at a new hotspot, Elbow Room. “It’s the smallest bar on the island, but they’re doing really delicious infusions with local ingredients.” Their take on the classic triple-rum-based Goombay Smash, for example, is enhanced with toasted vanilla pods, allspice, star anise and cloves. For dinner, he says Rock House in Dunmore Town is hard to beat, both for its vibrant sunset views and high cuisine. Located in a romantic, harborside 10-room boutique hotel, the restaurant features classic Caribbean fare with a modern twist, such as the pan-seared yellowfin tuna with avocado mousse and pickled ginger, or the seafood stew with snapper, shrimp, scallops and lobster simmered in a chili-tomato broth.

The embarrassment of riches that Eleuthera and Harbour Island offer is the reason for their sustained popularity among discerning travelers of all kinds. “There’s an ease and freedom to do whatever you want to do, but it’s perfectly acceptable to sit on your butt and do nothing,” Simmons cheerfully notes. “Freedom, relaxation—that’s what we’re ultimately providing.”

Stephanie Haede Dorsett
Stylish Taste on Harbour Island
Boutique Owner

Charlotte And Anna Fitzek
Vegan Café Owners

Stephanie Heade Dorsett grew up mostly in Germany with her Bahamian father and German mother, but she has plenty of childhood memories of the Bahamas. That’s part of what drew her to tiny Harbour Island 14 years ago. She and her daughters, Anna and Charlotte, had moved from Europe to Nassau, the Bahamian capital, but weren’t fond of the bustle. “For me, Harbour Island had the perfect mix of island life as I remembered it, but sprinkled with restaurants, shops, a very diverse crowd of people, and of course the beach.” These days she runs Shine, an upscale boutique offering her own clothing and jewelry designs on one side of the street, and one-of-a-kind home goods on the other.

Affection for Harbour Island’s famous Pink Sand Beach runs in the family. “We go every day if we can,” says daughter Anna, who teaches oceanfront yoga and runs Sweet Spot Café with her sister, Charlotte. They opened the homey vegan breakfast and lunch spot in part because vegan fare was hard to come by on the island. From a cozy cottage they whip up cold-pressed juices and smoothies with local fruits, and their vegan lox bagel with cashew cream cheese and capers has become a hit among islanders and globetrotters alike. And, as this is the Caribbean, the sisters serve an unapologetically hedonistic selection of cocktails, including a dark rum mojito and a mango daiquiri.

For lunch, all three like to visit the Coral Sands hotel’s beach bar. “You’ll find everyone here, from fancy dressed-up people to those who’ve just walked up from the beach,” says Anna. “They have a very good Bloody Mary,” adds Charlotte, “nice and spicy.” Mom will occasionally eat with her daughters there, but she prefers The Dunmore hotel, just down the beach, for a slightly more elevated afternoon. “It’s so beautiful—it’s how you would want your island to look if you had one. And I think everybody who works there is happy, so they have really good service.” She’s a creature of habit when it comes to lunch. “I only get their truffle fries and a drink. I love those fries.”

Shopping on the island tends to be a high-end affair, and Heade Dorsett’s shop is no exception. Her selection of jewelry ranges from art-deco diamond rings to boho-chic necklaces, and her charming jellyfish sculptures, made from gold wire and gemstones, have become collectibles.

As for fashion, she designs her own vibrant prints and shapes them into flowy caftans. And when the island shuts down in September and October she travels, shipping back vintage one-of-a-kind housewares for her space across the street.

She says that despite the small size of Dunmore Town, its retail is impressive. “All the shops on the island, like Blue Rooster and Sugar Mill, are high-end and beautiful. Everybody has a different take and different things to offer.” Charlotte is also a big fan of A and A Hidden Treasures, where you can order personalized little purses and bags made from straw, shell and sea glass and watch them being assembled in front of you.

When they all go out to dinner, they’re in agreement as to the restaurant: Da Vine Sushi & Wine, which Heade Dorsett describes as looking like a chic Miami sushi bar inside a cute colonial house. Charlotte admits, “I do cheat and sometimes eat fish, and that happens at Da Vine. They have very good local grouper and wahoo sashimi.” Other unique items include conch carpaccio with chili garlic sauce and jalapeño salsa, and a Bahamian lobster roll with avocado and spicy mayo. “We love that they stay open late,” adds Anna. “Most places here shut down at 8:30.”

After dinner the family sometimes goes dancing together, usually at Romora Bay Resort and Marina, where the bar offers live music every Wednesday through Sunday night. “It’s on the bay side of the island, so it’s really nice to watch the sunset and have a drink,” says Charlotte. “They have an excellent frozen Goombay Smash,” a vacation drink if there ever was one, consisting of a medley of rums (coconut, gold, dark), apricot brandy, fresh pineapple and orange juice and pineapple slices. The bands specialize in rake-and-scrape, a Bahamian music genre peppy enough to turn songs like John Denver’s “Take Me Home, Country Roads” into dance tunes.

“I love that it’s a much simpler life here,” says Charlotte. “And at the same time, it’s not too quiet.” Sounds about right.

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