My very first trip to Bermuda was a pretty unforgettable one. I was in town during the final weekend of the 2017 America’s Cup, as Emirates Team New Zealand and Oracle Team USA faced off in a gripping race for the oldest trophy in sporting history, and all eyes were certainly on the water. Spectators poured in en masse to the America’s Cup Village at the Royal Naval Dockyard, watching the action from front-row seats at the Gosling’s Island Bar and several other focal points. In the gripping final round of the 35th iteration of the biggest regatta in the world, New Zealand prevailed over team USA.
Beneath the buzzing energy of the weekend’s main event, though, was the undeniable beauty of Bermuda itself— a 21 square mile cluster of 181 islands of varying sizes, together home to approximately 60,000 residents. Today, it’s a country aglow with the economic boost brought on by several years of preparation for the 35th America’s Cup, which has amplified the existing support system of thriving native Bermudian businesses like Gosling’s rum, a humble family operation dating back to 1806. It’s the pride of Bermuda, the thread that weaves many elements of everyday Bermudian life together for both locals and visitors, and it’s something special that no visit here is complete without. In short, to travel to Bermuda is to drink entirely too many Dark ‘n Stormies and Rum Swizzles while taking in the island in all its laid-back glory, so without further ado, here’s my ultimate rum-soaked guide to making the most of a weekend filled with pink sand beaches and beyond.
Friday morning and afternoon: Fly into L.F. Wade International Airport and breeze your way through customs before hopping in a cab bound for the Fairmont Southampton (just a 35 minute ride, give or take). This’ll serve as your home base for the weekend, its main draws being spacious guest rooms, a prime location, excellent dining options. an absolutely stunning beach club atop sparkling pink sand and quite possibly one of the best breakfast spreads in the Caribbean. Check in, get settled, throw on a swimsuit (and some sunscreen), and then head down to the bubblegum-pink beach club shuttle that awaits in front of the lobby. There’s a chaise lounge and an inaugural Dark ‘n Stormy from the Cabana Bar with your name on it.
Friday evening: Once you’ve had a healthy dose of sun, head back to the hotel via shuttle (or enjoy the 10 minute scenic walk up the hill). It’s time to freshen up for dinner and a night on the town in the capital city of Hamilton. After a quick change, the door attendants will be happy to hail you a cab, and you’ll be on your way to the Barracuda Grill for haute takes on Caribbean fare (and a Michael Douglas/Catherine Zeta-Jones sighting if you’re lucky). If you fancy a nightcap on the way back to the hotel, stop at The Swizzle Inn, a Bermudian classic, for (you guessed it) a round of swizzles.
Saturday morning: A good dive or boat outing is essential to any Bermuda itinerary. For those who wish to acquaint themselves with the vast marine life that surrounds the islands (or the 300+ shipwrecks that punctuate it), you’ll want to schedule a morning wreck dive, with which your concierge at the Fairmont will be happy to assist. Of note is the Mary Celeste, one of the most famous shipwrecks in the Caribbean, its celebrity due in part to the 2011 discovery of five bottles of perfectly preserved wine along with one bottle of wholly intact perfume from its 1864 sinking. The perfume was studied and replicated by the Bermuda Perfumery, where divers and history lovers alike can purchase a bottle of their own.
If you’d prefer to stay above water, you can either charter a boat or some jet skis, head out on a guided fishing excursion, or take a mini-cruise around a few select islands—these can each be arranged by your hotel concierge as well.
Saturday afternoon: You’ll likely be thirsty after a morning on the water, so grab a cab to the Gosling’s bottling plant on Dundonald Street in Hamilton, where you can buy a few bottles from the source at the wine and spirits shop. We’d recommend at least one bottle of the classic Black Seal along with the lighter (and newer) Gold Seal expression. You can also find Gosling’s brand ginger beer to make your own Dark ‘n Stormy cocktails; otherwise, there are also ready-to-go versions of the cocktail in a can, which make for lovely souvenirs for the island rum aficionados in your life. From there, if you’re still in a shopping mood, head over to Front Street for a stroll along the strip of boutiques; don’t miss out on Thirty Two° 64°, home of Coral Coast Clothing, a Bermudian-born and American-made collection of refined-yet-relaxed dress shirts, Bermuda shorts and accessories.
Saturday evening: Take the evening to continue exploring the area around Front Street; the restaurants along the harbor are not to be missed. Request an al fresco seat overlooking the water and enjoy the day’s fresh catch alongside a few more rum cocktails before calling it a night and heading back to the hotel via cab.
Sunday morning: As your Bermuda weekend comes to a close (and your suitcase fills up with souvenirs), there’s hopefully still time for one more activity: a spa treatment at Willow Stream right in the comfort of the Fairmont Southampton. There is, after all, no better way to end a beach vacation than with one last exercise in R&R, particularly where a 21,000 square foot wellness playground is concerned. You’ll be ready to take on the flight home with a clear mind and a fresh tan, plotting your next trip back along the way.