If Gabriella Khalil Builds It, The Stars Will Come

On any given day at Grand Cayman resort Palm Heights, you may find Pamela Anderson channeling Baywatch while shooting a campaign for Frankie’s Bikinis. Or the team behind Gohar World — culinary artist Laila Gohar’s irreverent, coquette-leaning home-goods brand — setting up a dinner on the beach to celebrate their new capsule collection in partnership with the hotel. Or frequent visitors like Chloë Sevigny or Emily Ratajkowski, lounging under the hotel’s signature yellow umbrellas. Then there’s the ever-rotating cast of creatives- and athletes-in-residence, like Somali professional boxer Ramla Ali, who’s been known to host boxing classes on the property. “It’s sort of like what you would imagine the Chelsea Hotel felt like back in the day, but in the Caribbean and really elegant,” says Anna Zahn, whose Ricari Studios is in permanent residence at the property’s Garden Club spa. “Except we’re not having bacon, egg, and cheeses, we're having kale salads and sushi.”

This is what the resort offers, even more than a pristine beach and top-tier service: a chance to hang with the cool kids. “You can go somewhere and there can be just the most beautiful interiors and the most perfect meal, but if there isn't the energy of the people, it kind of falls flat,” says Diotima founder and creative director Rachel Scott, who collaborated on Palm Heights’ boutique, Dolores.

In a world where most third spaces seem to exist more to impress your social media community than inspire any true sense of real life camaraderie — a problem many in the startup space are, unsuccessfully, trying to tackle — hotelier Gabriella Khalil has somehow managed to precipitate both virality and true connection. “The people she has around her are incredibly cool themselves, but they're there because of her,” Scott says.

Christened one of “the most powerful New Yorkers you’ve never heard of” by New York magazine, Khalil’s reputation precedes her — and with her jet black, hips-grazing, glass-straight hair, the 41-year-old appears plenty intimidating at first glance. But as we work our way through omelets and french fries over a late breakfast at The Odeon in Tribeca, Khalil is indefatigably modest, even reserved. “I’m always surprised at the recognition of the hotel,” she demures when I implore her to speak to its many triumphs, from landing the cover of Travel & Leisure to serving as the backdrop of Hailey Bieber’s recent GQ fashion spread. “I’m still really in it, and it’s this constant conversation about trying to make it better or do those new projects. So I don’t look at it like, ‘Oh, I’ve made it.’” (The only thing that came close? Anderson’s photo shoot. “That was a real pinch-me moment, 1000%. I couldn't believe she was there,” she says of the ’90s icon.)

The hotel isn’t the only project she’s currently in the weeds on. There’s Water Street Associates, a members’ club in the Financial District that boasts rooms full of cult-favorite Togo sofas and vendors like Ricari studios; last May, it served as the site of Ratajkowski’s Met Gala after-party. Over in Brooklyn, there’s Bushwick’s Scott Avenue Associates, which is now hosting pop ups on the roof like this winter’s Chalet: a fondue, raclette, and charbonnade restaurant that features a usable ice skating rink and a site-specific work by artist Christpher Myers. And then there’s Happier Grocery, New York’s answer to Erewhon, where you can exclusively purchase limited edition Oishii berries dipped in chocolate. In each space, Khalil sets the stage, then invites just the right mix of people to bring it to life.

When did she start stepping out from behind the coterie of well-known faces and become a woman-about-town in her own right? “That's an interesting question,” she says. “I don't know.”

Khalil never set out to become a hotelier. She was born and raised in Philadelphia, where she attended La Salle University before decamping to London to get her master’s degree at Sotheby’s Institute. After graduation, she worked in galleries and sold artwork to private clients before she began collaborating with her real-estate husband, Matthew Khalil, on staging homes as part of his business. From there, “It wasn’t like we were like, ‘Let’s do a hotel!’ It was this opportunity that came up and we were like, ‘Yeah, that could be interesting,’” Khalil says of opening the 52-suite Palm Heights in 2019. (The boutique hotel was then closed to international guests from March 2020 to late 2021 due to COVID restrictions.) “At the time I was like, ‘I’ll just do this for a little bit and then I'll go back to doing my other stuff,’” she says of the hotel, which is a family collaboration. “I definitely didn’t realize how much was going to go into it.” (Nor did she realize she’d wind up working alongside her other half, which she admits can be “challenging.” “Everything is a dialogue,” Khalil says.)

What Khalil considers to be naivete turned out to be her greatest asset. Relying on her penchant for collaboration and eye for design — like having Bode design the staff uniforms or incorporating a maximalist, North African textile-heavy aesthetic into a largely ‘70s-Caribbean-inspired interior — she was able to build something special rather than just another resort. “We were almost trying to layer the experience,” Khalil says.

“A lot of hotels now, and members’ clubs, have this ‘hosed-off’ feeling. But she invests in the feeling of hospitality and checking in on guests,” says Feed Me newsletter writer Emily Sundberg, who considers Khalil “the smartest hotelier in the world.” When you check into your room, a personally curated selection of rare books from their in-house bookshop, Library Fetish, is waiting for you. Bambi Grimotes, the hotel’s master of ceremonies and unofficial “mood director,” roves the property offering guests fresh-squeezed watermelon juice and colorful conversation.

To help lure the bold-faced names that have become synonymous with the hotel, Khalil conceived of a creative residency. “It wasn’t this thing where you get to come down and ‘take photos.’ It was like, ‘Come down, enjoy, and create,’” she says. (In addition to the residency, according to New York, “friends of the property” reportedly receive discounted rates.) “It was like, there's this chef [visiting] who’s writing a cookbook and they're going to do this [activation here]. Or you're on the beach and there's [a resident] over there painting something, and [guests will] be like, ‘That's wild.’”

Nowhere is this wow factor more apparent than at Habibi: the Levantine pop-up restaurant and hookah lounge on the roof of the still-under-construction Scott Avenue Associates. To enter, diners must pass through a car-sized roll-down gate to the back of a warehouse, then take a freight elevator — a potential roadblock that Khalil has transformed into the main attraction. The elevator cab is decked out in neon lights and palm fronds, and a tuxedo-clad operator pours guests glasses of champagne as they ascend to the heavily landscaped, but proudly industrial, rooftop overlooking the city.

“[It’s] this idea of surprising and delighting, which a lot of the hotels and hospitality groups were originally built on. But because of different prices going up in cities, and cost of labor and stuff, you sort have lost [that] over time,” says Sundberg. “But clearly, she's able to pay a lot of people to make this thing run so smoothly.”

Scorpios always have schemes and plans and things that are happening, and you're never going to know them all.

Balancing the kind of “if you know you know” mystique that attracts insiders with the mainstream, outsider-driven success that’ll actually keep Palm Heights afloat is precarious. (Will the yellow umbrella still appear cool after popping up in the grids of normies everywhere?) So far, though, Khalil’s managing it — perhaps because the normally fickle insiders are sticking around, in no small part thanks to her. But much like Khalil’s properties, there’s more to her than meets the eye.

“Gabby is really good at being warm, but keeping a level of privacy. It's actually masterful,” says Scott. “Then once you get to know her a bit more and she feels comfortable, [she’ll do things like] at her birthday party last year where she got on the mic and sang ‘Shoop’ by Salt-N-Pepa with an excellent delivery. I was like, ‘Wait a second, that's Gabby?’” Designer Christopher John Rogers had a similar experience: “As I've gotten to know her better over the years, her unique sense of humor and levity has emerged, and is a lovely counterpoint to her mysterious exterior,” he tells Bustle.

As Khalil well knows, it’s best to have layers. “Scorpios,” Zahn says of Khalil’s rising sign, “always have schemes and plans and things that are happening, and you're never going to know them all.”