How to Enjoy the Ultimate 4-Day Weekend in Bermuda

Hiding in the Atlantic, Bermuda is often overlooked for its Caribbean counterparts farther south. In fact, it’s the closest resort getaway for many Americans. The 21-square-mile, subtropical island is about 600 miles off the coast of North Carolina, making it the perfect destination for a long-weekend escape. Its palm-lined streets, aqua waters, and pink sands entice visitors year-round. For consistently sun-fueled days that are ideal for enjoying all Bermuda has to offer by land and sea, we suggest booking your trip between May and October. Here’s what to know before you go.

Bermuda beach at sunset
Konstanttin / Shutterstock

How to get there

Though many travelers associate the island with cruising (a popular option for getting here), those who want to get the most out of four days in Bermuda should opt for a 90-minute flight to the island from an East Coast hub. There are year-round flights from Boston, New York City, Newark, Philadelphia, and Miami. Upon arrival, few attractions are more than 30 minutes away—though you’ll feel “a world away” as the island’s slogan boasts.

Beachside exterior at the St. Regis Bermuda resort
St. Regis Bermuda Courtesy Image

Where to stay

St. Regis Bermuda: As Bermuda’s newest resort, and the island’s first new luxury hotel brand in 50 years, the St. Regis Bermuda is a revered retreat at the east end of the island. The 120-room hotel overlooks a private inlet known as Gates Bay where the island’s founders were shipwrecked in 1609. Today, the property’s protected beach is lined with loungers and cabanas for guests to wile away a carefree afternoon. If you prefer a day by the pool, a pair of gorgeous infinity pools overlooks that spectacular beach where Bermuda’s selling point is never out of view. Take a short taxi into St. George’s for a walk around the historic town. Then, walk up to Fort St. Catherine to appreciate the protective fort system in place from the 17th century. Or pop over to Tobacco Bay for a taste of the local scene—where Sunday afternoon parties are the place to be.

The Loren: Centrally located with easy access to one of Bermuda’s pinkest sand beaches, The Loren is a posh hideout with a delightful program of culinary and cocktail events to keep guests experiencing something new every night. All 45 of the oversized, suite-style rooms are outfitted with large balconies to enjoy Bermuda’s south shore palette of turquoises from sunrise to sunset.

Rosewood Bermuda: This upscale resort is an island stronghold, having redefined the island’s luxury offerings upon opening in 2009. Though the property is suited for every traveler, from honeymooners to families, it’s a natural magnet for golfers. Set on 200 acres of groomed fairway, Rosewood Bermuda offers direct access to the 18-hole, Par-70 Tucker’s Point Golf Course, originally designed by Charles H. Banks and redesigned in 2002 by Roger Rulewich. The guest rooms were completely renovated in 2018, as were the public spaces, including the addition of a 12,000-square-foot spa.

Long shot of Bermuda's Horseshoe Bay
Bermuda’s Horseshoe Bay Alexander Sviridov / Shutterstock

What to do

Beach it: It’s tough to plan any itinerary in Bermuda without factoring in its spectacular beaches—a definitive experience whether swimming, walking, beach-hopping, or simply lazing. Most of the finest strips of sand line the island’s south side. A few favorites are Horseshoe Bay, Warwick Long Bay, and Cooper’s Island Nature Reserve.

Street scene in downtown Hamilton, Bermuda
Downtown Hamilton Darryl Brooks / Shutterstock

Stroll through downtown Hamilton: The pastel storefronts and tiered white roofs of Hamilton make it hard to believe it’s a capital city—let alone a global insurance hub. Of course, as a visitor, you’ll be more interested in popping into the colorful souvenir shops, local boutiques, and British-style pubs reflecting the island’s Commonwealth ties. Don’t forget to pick up a rum cake or bottle of Goslings rum to bring a taste of the island home to your loved ones.

Seaside golf course in Bermuda
rusty426 / Shutterstock

Golf: From Port Royal to Mid Ocean and Tucker’s Point, Bermuda has one of the world’s highest concentrations of pro-standard golf courses. Whether you’re a scratch golfer or a casual player, you’ll enjoy the varied greens and sweeping views accompanying them. Just be sure to secure an early tee time before the heat of the day sets in.

Go diving: As divine as Bermuda’s blue waters are to admire by land, they’re an entirely different world when experienced below the surface. Scuba diving outfitters like Dive Bermuda and Blue Water Divers and Watersports are found throughout the island, encouraging all levels of divers to go deeper—but you don’t need to be scuba certified to appreciate the island’s coral reef system. Snorkelers, helmet divers, and mere floaters can enjoy the marine life brimming just a few feet under.

Swizzle cocktails at the Swizzle Inn
Bermuda’s rum swizzle always packs a punch. Courtesy Image

Where to eat and drink

Swizzle Inn: Yes it’s touristy, but the Swizzle Inn (sharing a name with the island’s favorite rum drink) is a Bermudian institution—and reputedly the best place to slurp a swizzle on the island. On any given night, you’ll find just as many locals as visitors here slurping back jugs of this potent concoction. Dine here for lunch or dinner. Just be prepared to “swagger out” (as their slogan warns). This rum cocktail mixed with a variety of fruit juice and grenadine packs quite a punch.

Seabreeze: Al fresco dining is one thing, but beachfront terrace dining is in a category of its own. The latter is what you’ll be savoring at Seabreeze on Elbow Beach. The tapas restaurant is known for its sushi and accompanying small plates served with an equally luscious view. Come at sunset for a particularly magical setting.

Barracuda: Located on a side street in downtown Hamilton, Barracuda serves up some of the island’s freshest catch in a fine-dining setting. On a hot day, the air-conditioned atmosphere is definitely where you want to be—and as far as local flavor goes, the Bermudian scene here is also pretty hard to beat. After dinner, head downstairs to Hog Penny, a British pub hosting live music late into the night.

Blu: On the way to Bermuda’s west end, you’ll discover Blu—a hidden gem for tourists perched above Belmont Hills Golf Course overlooking the harbor. The top-end eatery serves an indulgent menu of steak, fresh fish, and sushi—all worthy of a terrace reservation with a bottle of fine wine (from an extensive list of them). You’ll want to time your meal with sunset as the views here are unparalleled.

Art Mel’s: This back-of-town fast food joint is a local favorite—especially after a night of copious rum. Art Mel’s double-decker fish sandwich (fried local fish wedged between a raisin bun smeared with tartare and hot sauce) is the closest thing to a regional delicacy that Bermuda offers. If it’s too far out of the way on your quick weekend trip, be sure to scout out a fish sandwich somewhere. Most restaurants flaunt them on the menu, all providing their own delicious twist.

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