The Ultimate Packing Guide for a Trip to Bermuda

On a typical day in Bermuda, you could be going from brunch at Cambridge Beaches to a stroll on one of the island's many pink sand strips, then to an alfresco meal at hot spot Huckleberry Restaurant. All to say, if you're a carry-on purist, you need shoes that can do double or even triple duty. These Dior slides feature embroidery that makes them dressy enough for a white-tablecloth meal, while they're equally at home either poolside or by the ocean. The oh-so-Bermudian powder pink shade is a slightly updated take on neutrals.

Bermuda's rose-colored beaches are rightfully some of the most famous oceanfront in the entire world, and with over 40 strands and bays that are easily accessible, it's relatively simple to find a quiet one—a rarity on many other islands. The remote feel of Jobson's Cove is cocooned inside striking cliffs, but there isn't much shade. Supergoop's spray SPF is a breeze to apply, is sweat- and water-resistant, and has antioxidants and vitamin C in the formula.

The retro cut and floral pattern of this one-piece are perfect for an island vacation. Pair it with linen shorts while you're window shopping in Hamilton. Dress it up with tailored pants for dinner at Bolero Brasserie, known for its tapas. And of course, it's also great as intended—wear it snorkeling inside the famous Blue Hole mangrove pond at Walsingham Nature Reserve.

This elegant cocktail dress by Giambattista Valli looks as chic at dinner as it does at a lingering lunch at the golf club. Reserve a table at Sunken Harbor Club, where the cocktails and views are fantastic. Try the Yellow Tang: vodka plus banana, pineapple, and passion fruit.

As frequent travelers to Bermuda know, it's not in the Caribbean—in fact, it's an archipelago of islands located in the North Atlantic Ocean. So depending on the time of year, plan on bringing a light jacket for the evening or when the wind picks up. This slightly boxy piece from Rails feels very modern; the Original Blue color is the perfect complement to everything from a sundress to a pair of sweats for the plane.

There's no bigger workhorse in a vacation wardrobe than a perfectly broken-in pair of denim shorts. AGOLDE's version has a flattering high-waisted fit and is just distressed enough to work at the beach or a night out. Ideal for a casual seafood dinner at Gulfstream (beloved for its fish chowder and spiny lobster), these make for an elevated evening look with a simple linen button-down, gold hoops, and a vintage scarf.

An island vacation is no time for protracted hair styling. Ditch the blow dryer for this texture spray, ideal for warm-weather climates like Bermuda. It won't leave your hair dry or sticky, and the light banana scent is delightfully tropical.

With so much to see in Bermuda, you'll need a shoe that can keep up with the touring. These Prada espadrilles are not only comfortable enough to wear as you explore the historic town of Saint George's (a UNESCO World Heritage site); they are elegant paired with linen pants or sundresses in the evening too.

Matching sets may just be the secret to packing for a tropical vacation. If you scoop up a breezy shirt-and-shorts combo, like this one from Alexander Wang, you can wear the pieces together or separately, and layered or unlayered, depending on the weather. This look is an ode to the beautiful pastel colors of Bermuda's houses.