Five Beach Towns We Love (And You Will Too)

Five Beach Towns We Love

From Key West to Trancoso (with stops in Marbella, Bermuda, and Hawaii), here's where to chase sun in 2015


This entire package originally appeared in the March 2015 issue of Virtuoso Life.

This story features five beach towns as inspirational destinations for 2015 and beyond; you can navigate to each town's description and activities by using the arrows under each section. If interested in traveling to any of these destinations, contact your Virtuoso advisor; if you don't yet have an advisor, click here to connect. (If you're unfamiliar about the benefits of working with an advisor, investigate those in the sidebar at the right on this page.)

First Up: Key West

Key West
The Sophisticated Side of Florida's Famously Laid-Back Island

Travelers come to Key West for golden sunrises over the Atlantic and purple-rose sunsets on the Gulf of Mexico, for schooner sails and bicycle rides. But the island has an upscale side that’s not to be missed.

(Section authored by Judy Kirkwood)

WHEN TO GO: Winter tourism dwindles from March through May, and bargains surface in summer (hurricane season), but the weeks before Christmas are the least crowded.

DINE AND DRINK: Feast in your flip-flops under a palm-thatched roof at local favorite  Hogfish Bar and Grill on Stock Island. Try the native pink shrimp and, of course, the hard-to-catch tender, buttery hogfish. Alfresco dining at Sunset Key’s Latitudes is Key West’s upscale, torch-lit choice for dinner and a sunset. At Louie’s Backyard Upper Deck wine bar, set in a Victorian mansion, drinks come with a view – and small-plate dishes plus truffle-butter popcorn. Sneak through an unmarked door in the historic Porter mansion (also home to The Porch beer and wine bar) for classic cocktails at newcomer The Other Side.

SHOP: Bésame Mucho stocks moonstone rings, artisanal bath and body products, silk ribbons, waxed canvas totes, and other tasteful treasures. For authentic figurative Keys and Cuban art, check out The Gallery on Greene. A block away, Lucky Street Gallery features more contemporary, cutting-edge fine art.  

BEACHES: You have to know where to look for a sandy beach on Key West. Fort Zachary Taylor Historic State Park offers woodsy nature trails, biking, and great snorkeling. Go to Smathers Beach for water-sports rentals. Both Sunset Key and Casa Marina have large pools and sandy beaches.

SOUVENIR: Take home a rum cake or white rum made with Florida sugarcane and infusions of coconut, vanilla, crème brûlée, or real key lime at Key West First Legal Rum Distillery.
Lazy Dog, at the 4.2 mile marker on U.S. 1, offers stand-up paddleboard yoga classes and moonlight meditation paddleboarding through shallow mangrove creeks.

DON’T MISS: Mallory Square is famous for its sundown antics, but for a more intimate experience, sail into the sunset (with Champagne) on one of Sebago Watersports’ boats – the schooner Appledore II, catamaran Flyer, or another from its fleet.

Next Up: Kailua, Hawaii

Oahu's Low-Key, White-Sand Destination

For decades Kailua was Oahu’s local getaway, a sleepy town on the island’s windward side known for stunning beaches and a relaxed vibe. New development and an influx of visitors have brought fine dining and shopping, but Kailua’s barefoot charm endures. 

(Section authored by Michael Shapiro)

WHEN TO GO: May through July, after the rainy and occasionally chilly Hawaiian winter, but before the swelter of late summer and autumn.

DINE AND DRINK: For steak and local seafood or an afternoon cocktail on the lanai, Buzz’s Original Steakhouse is one of the only restaurants by the beach in Kailua (it’s one of the oldest too). Formaggio Grill in the center of Kailua town offers Windward Oahu’s best wine selection. And don’t miss a shave ice at Island Snow near Kailua Beach Park; the frozen treats are good enough for the Obamas, who are known to drop by when they’re in town.

SHOP: At Mu‘umu‘u Heaven designer Deb Mascia brings vintage muumuus (and vintage fabrics) to stylish new life. Twin Islands is where Kailuans go for surf- and beachwear created by local waterman Mike Miller. Hawaiian-made line Fighting Eel specializes in spare, sophisticated women’s knitwear from island designers Rona Bennett and Lan Chung.

BEST BEACHES: It’s often said that Lanikai, at Kailua’s southern end, is Hawaii’s most beautiful beach. The half-mile stretch of ultrafine sand fronts a topaz lagoon stretching toward the twin peaks of Na Mokulua, two islets easily reachable by kayak or stand-up paddleboard. Lanikai’s calm waters are ideal for swimmers and families with small kids. For a more expansive strand, head just north to Kailua Beach, which edges the town for two and a half miles. Bring an umbrella; shady spots are prime real estate at midday.

SUNRISE, MOONRISE: It’s a short, steep hike to the top of Lanikai Ridge for sunrise viewing from WWII-era concrete bunkers, which locals call the “pillboxes.” Or skip the hike and just walk to Kailua Beach at dawn. Not a morning person? Kailua’s full moonrises are just as memorable.

THE BIKE FACTOR: Kailua is small, flat, and eminently bikeable. Rent a beach cruiser and pedal around Lanikai, through Kailua Beach Park, and back to town, stopping to swim wherever you feel the urge and ending at Lanikai Juice for an acai bowl.

GIVE IT A TRY: When the winds are up, Kailua is Oahu’s premier kite-surfing beach; when it’s calm, the stand-up paddlers are out in force. Rent gear or take lessons from one of several tour operators in town.

Up Next: Marbella, Spain

Timeless glam (and newfound sportiness) in Spain

Spain’s glitziest beach town is undergoing a renaissance. The yachts and exclusive beach clubs remain, but visitors are as likely now to hit the links or a mountain-bike trail as the designer boutiques.

(Section authored by Jeff Koehler)

WHEN TO GO:  While high season is July and August, the sun shines here 320 days a year. Spring brings warm weather and orange blossoms.

DINE AND DRINK: Marbella-born Dani García recently relocated his eponymous two-Michelin-starred restaurant a mile down the beach from the Marbella Club. Its 16-course tasting menu focuses on flavors, innovation, and technique rather than gastro-pyrotechnics. Kick off a casual night out at the newly opened Taberna Casablanca with a fino sherry and a handful of tapas, including salpicón de marisco (marinated seafood salad) and Spain’s iconic cured ham, jamón ibérico.

SHOP: The exclusive marina Puerto Banús has boutiques from every major fashion label. For homegrown shops, head to Old Town. D·Oliva carries 80 varieties of premium Spanish extra-virgin olive oil in attractive tins and bottles.

LOCALS KNOW: Summer means fresh sardines grilled on bamboo spits over olive wood embers at one of the numerous open-air chiringuitos (shacks) along Marbella’s beaches.

CHILL AND DANCE: The Moorish-like palace Olivia Valere draws upscale revelers. To dance in the sea breezes, hit Nikki Beach, with its sexy vibe and water shuttle to yachts and sailboats moored offshore.

DON’T MISS: Old Town in Marbella’s center is a labyrinth of meandering lanes and narrow alleys, an authentic and refreshing slice of ancient Andalusia.

STROLLING: Stretching five miles from Marbella to Puerto Banús, the waterfront paseo is perfect for jogging, cycling, or just strolling.

BEST BEACHES: The beaches to the east side of town, including Los Monteros and El Rosario, are sandy and remain shallow 50 yards out. To sunbathe with the famous and fashionable, head for Nagüeles Beach at the heart of the Golden Mile.

OFF-SEASON SWIM: The Marbella Club has two heated seawater pools, one indoors.

GOLF: There are more than 60 courses within less than an hour’s drive, including the legendary Valderrama in Sotogrande, 40 miles southwest – there’s a reason this area is known as the “Costa del Golf.”

ADVENTURE:  Hike up La Concha, the coiling peak that towers 4,000 feet behind town. Stunning views reward those who make the five-hour round-trip trek from the Juanar nature reserve.

Up Next: Hamilton, Bermuda

Rosy days in Bermuda

Forget the Bermuda Triangle. The triumvirate of renowned golf courses, pastel buildings, and local rum makes Hamilton a destination where losing yourself is far from harrowing.

(Section authored by Chaney Kwak)

WHEN TO GO: Thanks to 80-degree days, May through September are the most popular months. Locals like to wait until May 24, Bermuda Day, for their first dip in the sea.

DINE: On bustling Front Street, Red Steakhouse & Bar brings prime cuts of meat together with lobster and sea bass. Steps away, Port O Call serves fresh catches, such as wahoo, grouper, and snapper, occasionally alongside homemade pasta. At casual Hog Penny, the menu runs to Cajun-spiced lobster cakes and rum-spiked Bermudan fish chowder. The eclectic Tribe Road Kitchen turns out bacon doughnuts, quinoa tabbouleh, and anything else that inspires the chef, locally known as the “Barefoot Baker.”
SHOP: Fragments of the island’s famed pink coral are reborn as gorgeous accessories at Alexandra Mosher Studio Jewellery. Chatham House stocks a great selection of cigars. And, of course, there are the island’s iconic shorts: Bermudan-designed TABS, bright versions with a contemporary cut, are available at shops such as A.S. Cooper Man.
BEST BEACH: Warwick Long Bay’s half mile of pink sand stretches between cedar trees and tame waves. Swim alongside parrot fish and lobsters (but keep your distance from snapping turtles) around the coral archipelago, less than 200 feet offshore in the crystalline water.

HAPPY HOUR: The intimate rooftop at Muse is a great place to mingle with after-work locals and after-sun vacationers over tapas and house cocktails such as the Ritz Fizz, made with amaretto, blue curaçao, lime cordial, and – this is a vacation, after all – Champagne.
LOCALS KNOW: Horseshoe Bay is understandably one of Bermuda’s most popular beaches, thanks to its pink sand and gentle waves ideal for bodysurfing. But walk east on a nameless trail and several sandy coves await – with the same stunning scenery but without the crowds.
GIVE IT A TRY: During Classic Vacations’ 90-minute rum cruise (ask your Virtuoso advisor to book it), passengers sample distinct styles of the beverage, one of Bermuda’s most important exports – as well as a Dark ’n’ Stormy, the national drink, made with Gosling’s Black Seal rum and ginger beer.

Up Next: Trancoso, Brazil

Rustic refinement in Brazil

Beautiful people in (and out of) tasteful couture, sugar-textured sand, and clay homes in lollipop shades make this Bahian outpost one delicious beach destination.

(Section authored by Chaney Kwak)

WHEN TO GO: Trancoso’s summer – the Northern Hemisphere’s winter – has balmy, breezy weather and lively parties. March and April (Brazilian fall) bring clear skies without the large crowds.

DINE & DRINK: The town’s best restaurants and bars line the Quadrado, the see-and-be-seen green square onto which Trancoso nightlife spills nightly. One of the original fixtures, Capim Santo became so beloved for its fresh seafood that its chef opened a São Paulo offshoot. Traditional Brazilian fare such as carne seca com abóbora (dried beef with pumpkin) shines at O Cacau. At El Gordo, you can admire the bar and restaurant’s clifftop views while sipping cocktails made with one of the dozens of cachaças on offer.
SHOP: Find handcrafted wood decor and furniture at Marcenaria Trancoso, or pick up bikinis and board shorts from two of Brazil’s most celebrated beachwear designers, Adriana Degreas and Osklen – both have shops on the Quadrado.
BEST BEACH FOR SCENERY: A three-mile walk from the Quadrado along golden sand leads to Rio da Barra, so impressive that fifteenth-century explorer Pêro Vaz de Caminha made a special note about its red-and-white cliffs in his letter to the king of Portugal.
DON’T MISS: Swim in low-tide pools formed by reefs at Praia do Espelho, a secluded stretch of sand reached only by boat or an unpaved road.
HAPPY HOUR: Sip rejuvenating coconut water at one of the barracas, or beachfront bars, that pepper Nativos, the closest beach to town.
NEW IN TOWN: Teatro l’Occitane, a year-old theater whose architecture emulates the town’s cliffs, waves, and shells, hosts the Música em Trancoso festival. This year’s event (March 7 through 14) features works by Gershwin, Bernstein, Ravel, and Saint-Saëns with themes such as “From America to France,” plus tango, bossa nova, and more.
LOCAL CULTURE: Surf by the beach or take capoeira lessons at the Casa da Cultura. 

Top Travel Destinations
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