When Ben Simmons and Charlotte Phelan first met, the last thing either of them could have imagined was that together they would end up running the Ocean View Club, a storied hotel on Harbour Island, a three-mile-long cay off the Bahamian island of Eleuthera.
They were in Ireland, for starters, a world away from the tattered luxury, pale-pink sands, and flat cerulean waters that have been drawing an eclectic crowd to the hotel for generations. They were also children: He was 8 and she was 12, two kids with little in common aside from the fact that they were attending the same boarding school—and happened to share a birthday. “I used to bring Ben cake in the junior dining hall,” said Charlie, as she prefers to be called, one recent afternoon as she organized the liquor bottles behind the hotel’s bar. “But a four-year age difference is an eternity when you’re that young, so that was pretty much the extent of our relationship. The idea that we’d be doing this”—she gestured toward the hotel’s homey kitchen, where Ben, a chef, was baking bread for the evening’s meal—“is one of those things that reminds you that life is crazy in the best of ways.”
The Ocean View’s bar was a fitting spot for Charlie, a sprightly 34-year-old who could serve as a stand-in for Naomi Watts, to be telling this story, since it was in this cozy nook that she and Ben reconnected five years ago. She had flown from her native Ireland to Harbour Island for a friend’s wedding and had ended up—as visitors to the island often do—at the hotel for an intimate, boozy gathering of friends. Running into Ben was not exactly a shock. He had been raised on the hotel’s lush, rambling grounds by his mother, Pip, who had owned and operated the property since the late seventies. “What I didn’t know is that I would fall in love with him in about five minutes,” Charlie went on. “We talked all night, and three months later I had packed up my life back home and moved here.”
Just then, Ben, a boyishly handsome 30-year-old, came over. “Still, running the hotel was never part of the plan,” he said. “This was Mum’s place, and in a lot of ways it always will be.”
Indeed, to locals and regular guests alike, the 14-room Ocean View has long been known simply as Pip’s Place. A singular force of nature, Pip hardly fit the traditional mold of someone in the hospitality business: Brash, opinionated, sardonic, with a keen aesthetic sensibility and a cigarette perpetually dangling from her lips, Pip ran the place as an extension of her personality and tastes, creating a retreat that occupied that sweet spot between a boutique hotel and a bed-and-breakfast, and stood in stark contrast to the glossy resorts that dominate the Caribbean hotelscape. A chef trained at the Cordon Bleu in Paris, she did all of the cooking, feeding guests at communal tables (a typical meal in those days would consist of coconut-lemongrass lobster curry and platters of grapefruit with avocado, toasted pine nuts, and pomegranate), and ran the bar on the honor system: You mixed your own drinks and kept a tally in a leather-bound notebook. A fervent collector of antiques, Pip would redo the decor each season, making the Ocean View a place that was always familiar but never stagnant.
In the early eighties, photographer Bruce Weber discovered the property during a photo shoot, and soon after the Ocean View became a mandatory destination for the fashion set: Photographer Gilles Bensimon, Naomi Campbell, and Cindy Crawford all stayed here during shoots, finding comfort in its chill, anything-goes vibe. “There weren’t many hotels on the island back then,” Ben recalled, “and there was nowhere else like this. Mum kind of gave them the run of the place but would be happy to cook a meal for 30 people at two in the morning if it was that kind of night, which it often was.”
Two years ago, however, Pip put the hotel on the market—partly from fatigue and partly from her disenchantment with the culture. The island was more developed—the rickety golf carts that have always been the vehicle of choice now share the road with more cars than ever—and she was frustrated by what she saw as a new breed of traveler, who seemed more interested in staring at a smartphone than befriending strangers during late-night chats. And the fashion crowd, which accounted for 70 percent of the hotel’s revenue through 2008, had become less reliable thanks to recession-era budget restrictions.
At the time, Ben and Charlie were running a wedding-planning company and were in the process of turning a piece of undeveloped land on neighboring Eleuthera into a private beach with vintage tents. “We thought, Why not merge the wedding business with the hotel instead?” Ben said. “So we made an offer to Mum, and with her blessing started this adventure.” For Pip, who now runs a nearby clothing boutique, giving her son control of the Ocean View made sense. “I inherited the place from my mother,” she recalled one recent afternoon. “So now it’s Ben’s turn to do what he wants.”
Since taking over two years ago, Ben and Charlie have put their own stamp on the property while honoring its spirit. The decor remains a funky, ever-evolving mélange (the newly acquired floral-print sofas were sourced from Turkey; the teak Louis XV pieces from Belgium); the bar is still run on the honor system (with a new leather-bound book to record the tabs); and meals are now served outside, under the billowing white tents that Ben constructed to shade the hotel’s expansive patio. Two guest rooms have been added—airy tented structures overlooking the water, painted in all white and christened “Tent Cottages”—and the rooms have Wi-Fi, which Ben knows is just the sort of upgrade that Pip long resisted on principle. “It’s about recognizing the times we live in without ruining what makes this place so special,” he said. The fashion crowd have returned, though now they’re joined by young couples and families from the States and Europe. The Ocean View of today is a touch more polished than it was, yet its slapdash, bohemian spirit very much prevails.
Running the hotel is a seven-day-a-week gig, and Ben and Charlie’s constant presence on the property—whether in the kitchen, behind the bar, or fielding reservations in their small office—allows guests to feel like characters in their storybook romance. Still, the couple make a point of finding time to themselves, most notably on their shared birthday, the same one they celebrated a lifetime ago in their Irish boarding school. “Now we have a much better tradition,” Charlie said, describing how, every March 13, the two of them fill the back of their pickup truck with blankets and pillows and drive out to the beach with a bottle of wine. “It’s been a crazy, nutty year,” she added, “and it’s only going to get busier with a baby on the way in June. But it’s an insanity we’re very lucky to share together.”