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The next day, drive to the Royal Naval Dockyard, where you’ll find the British Maritime Museum, which allows you to explore old munitions
warehouses and tour current and staple exhibits such as the Bermuda Slavery
Exhibit, the Dockyard Glassworks (catch glassblowing and flame-working demos
daily), and the Bermuda Rum Cake Company (a working micro bakery). Sometimes
scent evokes more memories than photos, so visit the Bermuda Perfumery, where
you can pick up a fragrance that smells as sweet as you remember Bermuda to be.
Spend another day touring downtown Hamilton, where shopping (Louis Vuitton and
Max Mara), dining, and nightlife are the draws.
By Night
Bermuda is easily a foodie haven. Head to restaurant row on Bermudiana Road in
Hamilton for some of the best dining on island. Make a reservation at Portofino
Restaurant, a casual Italian trattoria with alfresco seating, or spice it up on
night two and head to Latin, one of Bermuda’s newest eateries, where the house-made sangria (get the red) perfectly
complements the savory paella.
For an upscale dining experience, make a reservation at The Point Restaurant & Terrace, where Queen Elizabeth II dined during a visit to the island late last
year. Be sure to bring your formal attire, though: The Point requires a jacket
for the gents. End the night strolling Front Street in Hamilton, where pubs and
clubs are open until later in the evening and the boats in the marina cast off
a soft glow, making it one of the more picturesque nighttime settings. Or
consider Elbow’s Veranda Bar & Terrace, an intimate rum bar where you can unwind with live music on Fridays
and Saturdays or enjoy a cigar on the outdoor patio.
When to Go
Bermuda sits close to the same latitude as South Carolina, so expect relatively
similar weather. High season begins in April, when the temps are moderate,
comfortable, and refreshing (think mid-70s). The best times of the year to go
are April, May, September, and October, the latter being less crowded, less
humid, and downright spectacular. 
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Mark Twain once wrote, “Bermuda is the right country for a jaded man to ‘loaf’ in. There are no harassments; the deep peace and quiet of the country sink into
one’s body and bones and give his conscience a rest.” Decades later, Twain’s words still ring true. There’s something magical about Bermuda, a certain je ne sais quoi, if you will. It’s possible that it’s the locals—friendly and helpful. Or the signature pink-sand beaches, the plentiful
nightlife and dining options, and the moderate temps (read: 80 degrees in
October).
But what’s more likely is that it’s the island’s proximity to the eastern United States—it’s a direct, two-hour flight from more than a half dozen major cities (Boston;
New York City; Philadelphia; Washington, D.C.; Charlotte; Atlanta; and Miami).
All of which means that instead of allotting two full days of travel for your
long weekend, you can instead enjoy that time on one of Bermuda’s stunning beaches, on a tennis court or golf course, or at a spa.
Where to Stay
To truly experience Bermuda’s rich English culture, which is a perfect mix between island charm and British
pomp and circumstance, consider Elbow Beach, a Mandarin Oriental property. Situated
centrally among downtown Hamilton (five minutes away), Horseshoe Bay, the Royal
Naval Dockyard, and Bermuda International Airport, Elbow Beach is one of
Bermuda’s premier hotels. The 235-room hotel (currently closed for a planned renovation)
sits atop fifty acres and overlooks Elbow Beach (the actual beach). Book one of
the premier ocean-view rooms in the area of Bougainvillea, one of seventeen
private cottage complexes. There, your private patio overlooks the ocean; best
of all, it’s just a one-minute walk to the private beach, which is possibly the biggest
draw to Elbow.
If new, grand, and intimate is what you’re looking for, consider Tucker’s Point Hotel & Spa, the only property to open in Bermuda in the past thirty-seven years. The
capstone of Tucker’s Point Club—Bermuda’s premier resort, private club, and residential community—Tucker’s Point Hotel & Spa boasts four lighted tennis courts, two freshwater infinity pools, and a
private beach. The eighty-eight guest rooms and suites represent a coupling of
British décor and modern amenities. Though the property itself is luxurious and
breathtaking, one of the property’s most appealing traits is its privacy. You can spend an entire week there and
not interact with another guest.
By Day
Make like a local and rent a moped. Skip the famous Horseshoe Bay, which is
packed with cruise-ship tourists on a daily basis. Instead, ride off on your
moped and spend the day at one of the more private beaches like Warwick Long
Bay or Jobson’s Cove.
