Check out our recommendations for what to do, where to go and what to eat in some of Cayman’s favorite overseas destinations this May.

A mural depicting (L to R) Ethiopian Emperor Haile Selassie I, Jamaican Reggae legend Bob Marley and his seven sons is seen on the ground of his museum in Kingston on June 30, 2012. Jamaica will celebrate its 50th anniversary as an independent state on August 6, 2012. AFP PHOTO / MLADEN ANTONOV (Photo credit should read MLADEN ANTONOV/AFP/Getty Images)

Kingston

Culture: Kingston is ground zero for West Indian arts, culture and political history. Pay homage with a visit to the National History Museum, the Jamaica Music Museum and to Liberty Hall. You can then bring the holiday back to the future with an evening at the Sankofa Sessions, a weekly live art installation event featuring artists, DJs and musicians.

Shopping: The magic is in the mayhem in Kingston. Program plenty of time for wandering to find some of the Caribbean’s best street arts and crafts. Start with South Parade, better known locally as “Ben Dung Plaza’,” for colorful street vendor stalls and Kingston’s soundtrack of choice, dancehall reggae, on blast.

Dining: Kingston has no shortage of trendy food and wine spots. Let your evenings fill up with the latest buzzing hot spots and kick off your day with the Western Caribbean breakfast of champions: a hot, fresh beef patty from Devon House Bakery.

Cocktails: Happy hour with the uptown set at Sky Terrace, where you can watch the sun set over the Blue Mountains while eavesdropping for the night’s best kept afterhours secrets straight from the mouths of the city’s most social dwellers.

Must Do This Month: The Jamaica Jazz Fest may draw you to Ocho Rios in the last week of the month, however you can keep it cultural and city-side with a visit to Artistic Dimensions 2016, a one-stop sensory experience in
culture and cuisine. Visit Eventbrite.com for more details.

 

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Palm Springs

Culture: California’s lesser-known desert locales are getting more famous, as the events they host (read: Coachella) gain more and more popularity. Live like the locals by booking a stay at the buzzy and iconic Parker Palm Springs where mid-century architecture, retro chic decor and an incredible desert spa experience make for the perfect #summervacay selfie.

Shopping: Design fanatics, you have found your Mecca. Palm Springs is an homage to all things trendy, yet classic, in interiors. Hone your hunt with a visit to the Uptown Design District.

Dining: When you are in a city that has its own dress code, you would do well to hit up the latest on-trend eatery.

Check out So.Pa at the newly-reopened L’Horizon Resort and Spa, boasting an entirely outdoor dining room, a fire pit and a mix of intimate, shared tables.

Cocktails: Embrace California-kitsch full on and hit up Bootlegger Tiki where the cocktails are craft and the tiki torches still burn with real fire after dark.

Must Do This Month: Don some fringe and get thee to Joshua Tree mid-month for the annual music festival. Joshuatreemusicfestival.com.

 

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Whistler

Culture: Located on Canada’s West Coast, Whistler culture is outdoors culture. Get familiar with the slopes at Whistler Mountain until May 20 (where you can ski in your T-shirt or bikini due to warmer temps) or wait until late May and enjoy stunning views from your own private gondola adventure.

Shopping: Whistler fashion is all about the accessories, namely the ones that protect your precious peepers. Start your trip with a trip to McCoo’s Whistler, a village favorite for stylish goggles that lend instant mountaintop street cred.

Dining: Fuel up in between outdoor adventures with a Buddha Bowl from the Green Moustache. The ski set stay in top form noshing on these filling rice and quinoa bowls, served up fresh with raw vegan chili, salads and fresh juice.

Cocktails: It’s all about the ‘apres’ all-day hangout in Whistler. Check out Merlin’s for music, food and drink on heavy flow throughout lunch and dinner, tucked conveniently at the base of famous Blackcomb Mountain.

Must Do This Month: Get your own goggle tan during Whistler’s best outdoor initiation, the Whistler Great Outdoors Festival (GO Fest) from May 20-23, four days of outdoors recreation and celebration. Visit www.greatoutdoorsfest.com for event information.

 

roatan

Roatan

Culture: The trick in enjoying this unspoiled piece of paradise is in the quiet time. Schedule time to commune with nature during a leisurely hike or spot capuchin monkeys on the Jungletop Zipline, one of the longest courses on the island.

Shopping: In the cruise port of Coxen Hole, shop for funky handmade wares at Made in Roatan, a non-profit shop and local labor of love where proceeds fund roughly 20 local Roatan families.

Dining: Enjoy a meal on picturesque French Harbour and enjoy some of the best seafood the Caribbean Sea has to offer. Geo’s is famous for its king crab and Temporary Cal’s Cantina offers one of the most stunning waterfront views.

Cocktails: Visit Sundowners for a wide selection of Honduran beer and sunset-watching. Up the fun factor on a Wednesday with a game of “Chase The Ace,” where each drink gives you a chance to draw an Ace and win cash.

Hint: it’s more fun to lose!

Must Do This Month: Book a diving or snorkeling trip. With Easter weekend behind us, Roatan’s spectacular beaches have slowed down, almost guaranteeing you a private spot for an invigorating adventure or a private trip for two.

Visit travel-roatan.com for travel information.

 

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Havana

Culture: Cuba is known for its native artisans, but no man paved the way for the island’s legendary place in literary history like Ernest Hemingway. Get a taste of “the old city” with a visit to Hemingway’s actual room, number 511 at the Ambos Mundos Hotel, where he famously penned “For Whom the Bell Tolls.”

Shopping: A Havana shopping list should include art, art and more art. Stop by Fototeca de Cuba – attached to the city’s best photography gallery – for a rotating and heavily-curated selection of Cuban prints.

Dining: La Cocina De Lilliam serves up stunning versions of Cuba’s most classic entrees in a private club-like setting. Order the ropa vieja, a traditional Cuban dish of shredded stew meat.

Cocktails: Times they were a-changing. And change they did at Hotel Nacional de Cuba. Enjoy a chilled beverage here simply for the historical gravitas; where Winston Churchill, Al Capone and Frank Sinatra escaped 1940s Havana heat with a cool drink.

Must Do This Month: This Month: Cuban rhythms and world-class choreography unite with the much-anticipated “Havana Queens” show run. This Broadway-esque presentation is Cuba’s answer to “Fame” with a passionate story line and incredible athleticism. We’re in! Visit Havanaqueens.ch for dates.