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Bermuda is weird, and not just in the sense that things famously disappear there. Unlike most of the islands in the Caribbean, no indigenous peoples were living there prior to the arrival of European sailors. Its history is about 500 years long—unless you count wild hogs—and linked intrinsically to its appeal among travelers from faraway lands. It's a satellite of the Caribbean with an actual winter (albeit a mild one), and a vacation destination where people routinely wear blazers and knee-high socks to dinner. Landing there from New York is jarringly quick—just over two hours, less time than it takes to drive out to Montauk in light traffic. You cannot rent a car there, only scooters, but you can scoot from one tip of the island to the other in less than an hour. In some ways, it feels less like an island than an island-sized country club. That said! Two hours from New York? Direct flights on Delta, American and JetBlue for about than the cost of a weekend-long Zipcar rental? Give me the knee-high socks. I’m in.
This year, for reasons both complicated (antiquated sporting rules!) and obvious (yachts!), Bermuda is host to the America's Cup. Should you go to Bermuda for the America's Cup, the main events of which kick off this weekend? No, absolutely not. For one thing, you'll get gouged on every rate and fare and fee within a hundred mile radius of the island. For another, do you even like sailboat races? Be honest with yourself. What you should do is go to Bermuda after the America's Cup, taking advantage of the massive capital investment recently bestowed on the island and its properties. That is, you should take advantage of all the money recently spent to bring Bermuda into the 21st century, but not for the specific reason all that money was spent. Here's how:
The Hamilton Princess is a big, old pink hotel, walking distance from the little downtown sector of Hamilton, complete with a spa, jitney service to a the beach, and three restaurants, one of which is helmed by and named after Marcus Samuelsson, the lauded Harlem chef and author. I stopped in to Marcus last summer, just after it opened, fully expecting it to be one of those Vegas-style offshoot restaurants with an absentee chef, but there was Marcus himself, working the (very crowded) room, shaking hands and smiling ear-to-ear. If you go in the summer, you’ll want to make a reservation. Regardless of when you go, you’ll want the Fried Yard Bird.
Bermuda is famous-on-instagram for its pink sand beaches, which aren’t really pink (not without a filter anyway) but, like, pinker than normal sand. One of the best pink sand beaches is Elbow Beach, and the Coral Beach Club has the best little somewhat-private sliver of it—and a very Mediterranean terraced dining situation overlooking the water. The Club is technically members-only (and people referred by members), but regular folk can get in via spa appointments and dinner reservations. There is a house parrot.
Like all the best islands, the shore here is encircled by a sprawling network of coral reefs. That means perfectly calm water, which is really good for people who like to just kind of float on their backs and zone out. I have also heard that some people like dive to look at reefs. I don’t understand that, but okay.
Standard dinner dress code pretty much island-wide is as follows: one of those stodgy gold-buttoned blazers, a tie, an inexcusably long pair of shorts, knee high socks, and clunky shoes. Reader: it’s really bad. You should not wear this, here or anywhere. But you should put on a good light blazer and a pair of loafers and one of those linen button-ups that only works on vacation, and then go out to a fancy steakhouse. Maybe it’s the tennis club culture, or maybe its the British influence, but white tablecloth joints thrive here. The Waterlot Inn, the restaurant at the Fairmont Hotel in the parish of Southampton, is the best of them—crazy expensive, but worth the splurge. It’s got one of those “JUST PLAY THE HITS” menus—Oysters Rockefeller, lobster bisque, a caesar salad, literally eight distinct cuts of steak—but the kitchen here knows that the only way to win with a menu like that is by imagining each as a kind of a high-end comfort food, going big on portions and cooking everything to soft, medium-rare perfection.
No matter where you dine, you’ll want a Rum Swizzle, named after the swizzle stick used to stir it. Bermuda isn’t the only Caribbean island to claim a swizzle as its national drink, but damn do they drink a lot of them here. It’s a mixture of Gosling’s Rum, Triple Sec, sugar, pineapple juice, orange juice, lemons and bitters. In other words, it doesn’t taste anything like alcohol and it’s trouble.
Another favorite drink on the island, this one actually, definitively invented here. Look, you’re on vacation. Let your socks down a little and have another drinks.