I Flew To A Secret Caribbean Island Billionaires Love & Now I'm Different
Canouan Island, you were good to me.

In a movie, the opening scene would begin like this: A pale, vitamin D-deprived fashion writer languishes in the phosphorescent glow of her laptop. Next to her is a window with a view of her Brooklyn block, bleak and barren of greenery—pure mid-winter dreariness. She can’t motivate herself to do any real work, so she blankly stares at her screen, mindlessly opening and deleting emails. But then, as if by fate, a message appears at the top of her inbox inviting her to… wait, where? Canouan Island? What’s that? She has no idea, but it sounds sunny and warm and, according to a quick Google search, appears to be located in a promising part of the Caribbean Sea.
Cut to a few weeks later and our lovely heroine—who (shocking surprise!) is me—is on a flight to this mysterious hot spot. At this point she, I mean I, have finally learned how to properly pronounce Canouan (it’s “con-new-on,” not “can-new-an”) and that it’s part of Saint Vincent and the Grenadines, an island country in the eastern Caribbean. Getting there is no straightforward endeavor; guests need to fly into Barbados, Saint Vincent, or Grenada to connect to a second flight into the island’s tiny local airport (on an equally tiny airplane). The scenic destination’s off-the-grid nature explains why, in recent years, it has become best known as a paparazzi-free beach escape for the upper echelons of celebrity society, including Leonardo DiCaprio, Meghan Markle, and Cindy Crawford. Many of its most regular visitors, however, are those wealthy enough to have private estates within the island’s rolling green hills—thus earning it a reputation as “where the billionaires go to escape millionaires.”
Where To Stay In Canouan
Alison Syrett Cleary
Alison Syrett Cleary
As for us plebs without vacation homes to retreat to? Luckily, there are three (still incredibly luxe) resort and rental options on the island to choose from: the Italian villa-inspired Mandarin Oriental Canouan; Canouan Estate and Villas, which has intimate residences for groups and families; and Soho Beach House Canouan, the breezy and coastal-cool hotel where I’m set to stay. I arrive after a long day of traveling misadventures, including a delayed connecting flight and a brush with the Barbadian law. (Let’s put it this way: The country has made wearing camouflage print illegal and I definitely did not know that when I chose my pants for the flight.) I’m exhausted, hungry, and sticky from a day stuck wearing my cold weather New York clothes in the tropical heat. But I’ve revived the moment I enter my suite. Decorated in wicker furniture and linen touches worthy of a Nancy Meyers movie, a gentle salt air breeze blowing through floor-to-ceiling doors, the room is a serene oasis. I pivot from my original desire to skip dinner with my group and shower, then change into a long, romantic red dress for a candlelit meal on the resort’s private beach jetty.
As we eat, I’m informed that although Soho Beach House will be my home base for the trip, the island’s three properties all work together to provide the best possible experiences for their guests. There is, naturally, plenty to occupy me on-campus where I’m staying—top notch Cowshed spa treatments, mixology classes, pool time with an ocean view—but there are also restaurants and activities to enjoy via the other estates as well.
What To Eat In Canouan
Alison Syrett Cleary
Food-wise, this proves to be particularly fruitful. On our second night we indulge in a Mediterranean-inspired dinner at L’Ance Guyac Beach Club at Canouan Estates. The seafood is fresh and perfectly spiced, and the waitstaff are warm and engaging—mid-meal they allow us to hijack their playlist and dance with us to Whitney Houston bangers.
A few other options to consider are Tide Bar & Grill (traditional chophouse dishes with a Caribbean touch) and Lagoon Café (seafood and tapas) at the neighboring Mandarin Oriental, and Alphonso’s, a local favorite specializing in hot buttery lobster, paired with a full array of sides like a vegetable-laced rice pilaf, cheesy potatoes, and fried plantains. Getting there requires a special trip across the water to the neighboring tiny island of Petit Rameau, but the effort is well worth it.
What To Do In Canouan
Alison Syrett Cleary
Alison Syrett Cleary
On the topic of boat rides, let’s talk a bit more about mine for a moment. Have you ever put on your hottest string bikini and sat on the helm of a privately chartered Von Dutch yacht as it zoomed across the open sea? If not, let me be the first to tell you this is a situation you should one thousand percent set up during your Canouan journey. Lounging on the deck, my hair whipping around my face and salt water lashing my legs, I feel like all my swimwear moments of the past had been leading to this one culminating moment. I was a Bond girl in the opening moment of the film, the fourth Charlie’s Angel—for those fifteen glorious minutes, even Demi Moore could never.
And while we were technically on this invigorating aquatic journey for the purposes of snorkeling in the clear waters of Tobago Cays before heading to lunch, I personally prefer the moment it provided to take pictures of what I now refer to as “Boat Alison.” Boat Alison, unlike Wan Winter New York Alison, brazenly poses for photos standing on the side of her sleek water cruiser wearing no more than a few triangles of wet fabric. She glows from her constant exposure to the sun’s golden rays (while wearing SPF protection, naturally). She doesn’t have time for nonsense like pants! But there might be a stretchy mini skirt hiding somewhere in her glamorously cavernous beach tote.
However, if Boat Alison is a confident vision in her long-neglected swimwear, Hiking Alison is something of a sweaty, panting mess. I discover this several hours later as I embark, dressed in a crop top and New Balance sneakers, upon what I assume will be an easy jaunt to the top of Mount Royal. At 877 feet, it is the island’s highest summit. Despite our guide's attempts to distract us with his best Shaggy impression—his rendition of “Angel” is excellent—I’m hyper-aware that much of our climb is more of a vertical, quad-burning march than a gentle uphill stroll. At the top, though, we are rewarded with a kind of gobsmacking view that looks like it was green screened into all my photos: endless stretches of aquamarine water dotted with rocky peninsulas, a sparkling cerulean sky. Honestly I'd do the whole thing again, even without the private concert on the way up.
All this said, not all the island’s picturesque vistas require so much legwork to take in. If you’re even less outdoorsy than me and want to cut straight to the good stuff, I’d recommend taking in the sunset from the 13th hole at the Canouan Golf Club. This is accessible via a quick golf cart ride, which in and of itself is part of the fun: you get to take in the views and shifting colors in the sky as you rumble your way up a hill. We do just this one evening and, upon reaching the top, are welcomed with champagne and snacks and some of the most gorgeous natural lighting I’ve ever encountered. Heaven!
The Grand Finale
If you take anything from my experience in Canouan, though, let it be this: Soho Beach House has the equipment for a full-on karaoke session. I learn this on our last evening on the property, which also happens to be one day before my birthday. After a decadent omakase dinner at the Terrace Bar (there were steak, salmon, and maki rolls) and more than a few tequila-based drinks, I’m delighted to find a full set up, including a DJ booth, laptop, and giant screen for reading lyrics, waiting for us. But in the spirit of What Happens In Canouan, Stays In Canouan, I’ll just say the subsequent hours prove to be a night for the books, right down to my surprise coconut cake and group serenade.
The next morning as I wheel my luggage to the check-out, I’m sad to say goodbye to my carefree Canouan alter ego and all her air-dried beach waves and flirty sundresses. But it sure is nice to remember she exists—and all it takes to say hi is a short jaunt through paradise.