Grand Cayman: The Caribbean island I keep returning to
Where to stay, eat, swim, and slow down on an island that’s worth visiting more than once
This is From the Window Seat, a series of deeply researched, design-forward dispatches for people who believe in the art of traveling well. From immersive itineraries to standout hotel reviews, each one offers everything you need to experience a place—or a property—with intention and great taste.
Ed. note: This trip was hosted by the Cayman Islands Department of Tourism. As always, I only share experiences that I genuinely love, and all opinions and recommendations are entirely my own.
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There are trips you plan, and then there are trips that find you. My third visit to Grand Cayman began as the latter, an invitation from the Cayman Islands Department of Tourism with timing felt almost suspiciously perfect: five days on a Caribbean island dedicated to the art of slowing down, arriving just before my birthday and the start of a new year of life.
And I almost didn’t make it.
Four airports. Two planes. A lost bag. And then: an emergency landing for an elderly man—a cancer patient, I later learned—flying with his wife to what may have been their last vacation together. The cabin bristled with impatience: delayed connections, disrupted plans.
About an hour later, after EMTs assessed him and cleared him to continue, we took off again. He and his wife were moved into my empty row, where they settled into the two aisle seats.
Once we reached cruising altitude, the sky transformed. It was golden hour, and it had taken on this hazy quality that made it feel like we were suspended somewhere between reality and a dream. Pastel clouds stretched endlessly toward the horizon, glowing in shades of peach, lavender, and pale gold. I’d never seen anything quite like it. Naturally, I started taking photos.
Despite how enchanted I always am by the view from the window seat, no matter how many flights I take, sometimes I feel a little ridiculous for it and get self conscious. But then I noticed him leaning slightly toward the window, watching the sunset too. Pure awe on his face. It struck me that this man, who had every reason to focus on pain or discomfort, or uncertainty, was still captivated by beauty.
And then all I could think about was how lucky we were to be there at all. My hellacious travel day was put into perspective. The lost bag, the delays, the endless rerouting…my problems became very small.
We all need the occasional reminder that the opportunity to travel—to see the world, to share a sunset with someone you love, to board a plane bound for somewhere beautiful—isn’t something we’re owed.
Read on for:
The hotel that’s become one of my favorites anywhere in the world
The beach that has ruined almost every other beach for me
The under-the-radar experiences most visitors miss entirely
The wellness experience that ended in a room full of snow
The spots I’ll be returning to on trip number four