It usually happens about two hours into the ride—when you’re sitting on the Hampton Jitney, accompanied by what feels like the rest of Manhattan, stuck in a swell of traffic as you inch closer to the coast. That distinct feeling hits: There has to be an easier way to do a weekend at the beach. With a little more planning and a passport, there is.
A British island territory with miles of soft sand beaches and clear blue water, Bermuda offers a mix of adventure (scuba diving around vibrant reefs and famous shipwrecks) and relaxation (rum cocktails and the aforementioned beaches). With direct flights that take under two hours from East Coast cities like New York, Boston, and Philadelphia, you can get there faster than it takes to get to Montauk (or the Cape, or the Jersey Shore) on a summer Friday, which makes spending just a few days on the idyllic island easily possible.
Plan a weekend biking to secluded beaches, tasting an unforgettable fried fish sandwich, and sipping fruity Rum Swizzles. Here’s how to make the most out of a weekend trip to Bermuda.
Sprawling beachfront resorts line Bermuda’s coast, but for a more intimate stay, book a room at the Rosedon. Built as a private home in 1906, the Relais & Châteaux property in Hamilton feels like vacationing in a past decade. Take complimentary afternoon tea under the blue awning on the breezy front porch of the stately white building, and afterward borrow a bike (with helmets and charming wicker baskets) to pedal around town.
Behind the main house, find a heated pool ensconced in a lush tropical garden growing banana trees and birds of paradise, and for an ocean swim, the hotel offers shuttle service to nearby Elbow Beach. Another option is the Elbow Beach Resort, offering ocean-view rooms, tennis courts, and a spa with locally inspired treatments like the Rum Swizzle Ritual, with a full body scrub, massage, and cocktail finale.
Named as a nod to Mark Twain, who visited Bermuda often, Huckleberry inside the Rosedon has a sea- and farm-to-table focus and an award-winning wine list. Marcus, at the Hamilton Princess hotel, is chef Marcus Samuelsson’s spacious waterfront eatery. After dining on dishes that made him famous (“Yep Chicken and Waffles”) and with a tropical twist (fresh sashimi), stroll around the property to gawk at the multimillion-dollar art collection with pieces by Warhol, Koons, Haring, and Banksy.
In downtown Hamilton, restaurants populate Front Street and the surrounding area. Devil’s Isle is a lively coffee shop by day, a seasonally focused café by night. Spiny lobster season is from September to March, and if your visit blessedly coincides with this window, order it here. (The meat tastes similar to a Maine lobster, but this crustacean is clawless.)
In St. George’s, situated on the northeast part of the island, casual, waterfront Wahoo’s is popular with both locals and visitors for its namesake fish tacos, fried fish nuggets, and spiced fish chowder. If there’s one can’t-miss dish on the island, it’s the Bermuda fish sandwich. Plenty of places make a great one—Mama Angie’s, Woody’s, Seaside Grill—but don’t miss the version at Art Mel’s Spicy Dicy. Traditionally done with wahoo or snapper, coleslaw, and tartar sauce, the massive sandwich tastes best paired with a cold ginger beer.
Along with the Dark and Stormy (made with Gosling’s dark rum and ginger beer), Bermuda is known for the Rum Swizzle, invented, according to its owner, at the Swizzle Inn in the 1930s. Stop by the oldest pub on the island to try the original mix of rum, fruit juices, and bitters. For elevated cocktails made from scratch and using locally foraged ingredients, visit the Birdcage, overlooking Hamilton Harbor.
Across the road on Front Street, Brew is a new coffee shop cum bar, with local beers and wines on tap. Also in Hamilton, Yours Truly is the island’s first speakeasy bar, with creative cocktails in a stylish, dimly lit space. On the way to Southampton, the Dock at the historic (and swank) Waterlot Inn has a beautiful bay backdrop, and just may be the most relaxing spot on the island to sip a glass of sangria and take in a fiery Bermuda sunset.
With about 75 miles of coastline, it’s not hard to find an uncrowded beach in Bermuda. And while you shouldn’t miss that, preferably with a Swizzle in hand, there’s so much more to explore. Tap into it all with Winnow. Launched by a local, the mobile app curates the most fun and worthy Bermudian experiences, from swimming with turtles or paddling around a shipwreck via glass-bottomed kayak, to going for cocktails at a local’s home.
For an only-in-Bermuda experience, book a two-hour foraging walk with local expert Doreen Williams-James. The Bermudian is famous on the island for her vast knowledge of edible plants and herbs, and she’ll share it with you on a lovely stroll around the Cooper’s Island nature reserve in St. George’s. Take a (literal) in-depth look at the island’s geology with a subterranean tour of Crystal Cave. Discovered in 1905 by two boys looking for their lost cricket ball, the dramatic cave is filled with a clear, ocean-fed lake and stalactites that date back over a million years.
Before heading home, shop the boutiques of Hamilton and St. George’s for island treasures. Vincenzo Della Valle makes handmade leather sandals in his namesake shop. The Capri-born cobbler will custom craft you a pair and serve you an espresso while you try them on. Find your new signature scent at the historic Lili Bermuda Perfumery, and for the ultimate Bermuda souvenir, choose a pair of colorful shorts from TABS (The Authentic Bermuda Shorts), which have been synonymous with island style for decades.
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