Winter in New York is gray and gross. Guess where it isn’t gray and gross? The Caribbean — and there’s probably no better time to escape there, whether you pick one island to visit or you travel to a few on a cruise, like one of Royal Caribbean’s last-minute deals. But if you’re actually getting away, then where in that sunny, island-dotted region should you spend your time? Every location is unique, with its own rhythm and vibe, much like New York’s own neighborhoods. Finding your perfect Caribbean cruise spot could be as easy as considering where you live, work, or spend your time — assuming that you like your usual ’hoods. Ahead, find our recommendations for where to visit.
If you live in Union Square, Midtown, Chelsea, or Hell’s Kitchen
Then visit Aruba
There may be no better island for an action-packed vacation than Aruba, and a vacation full of action is something residents of some of Manhattan’s busiest neighborhoods may find familiar. Watersports like kitesurfing, stand-up-paddleboard yoga, and bodysurfing will be welcome workouts, and when you tire of them, you can go hiking or off-roading through the cacti-lined terrain.
The progressive Dutch Caribbean island has sandy beaches on one side and rocky cliffs on the other, creating two very different vibes to explore. Find a bar at a westward-facing one and drink rum cocktails as the sun sets. Then continue the night at one the many casinos and oceanfront lounges and restaurants, where revelry keeps going until dawn.
If you live in Park Slope, Boerum Hill, Cobble Hill, or Brooklyn Heights
Then visit Curaçao
Imagine Amsterdam got a rainbow sherbet makeover, and you can begin to imagine why dwellers of some of New York’s prettiest neighborhoods will fall in love with this Dutch Caribbean island. Its diversity, progressiveness — it’s considered one of the most LGBTQ-friendly Caribbean islands — and rich cultural history are all sure to appeal to public-radio listeners in South Brooklyn.
Forty miles off the coast of Venezuela, the island pulls cultural influences from Latin America, Africa, and Europe, and every two weeks, Venezuelan sailors bring goods from the mainland to sell in a floating market. While its capital city, Willemstad, has plenty of shopping, museums, and local cuisine, you can go into full island mode at one of its 35 beaches, which range from small rocky inlets to large swaths of sand. Adventurous kids will want to swim with sea turtles at Playa Piskado, and adventurous adults (and big kids) will want to snorkel through one of the shipwrecks off its coast.
If you live in Soho, Tribeca, the Financial District, or the Upper East Side
Then visit St. Barths
Of all the Caribbean islands, St. Barths just might be the chicest and most exclusive — totally appropriate for the residents of an exclusive NYC zip code. It is a millionaire’s paradise, but more in a Gallic way than a showy one. And while you don’t exactly need a yacht parked in the harbor to enjoy its many splendors, it would help, considering there are no direct flights to the island (those without a private yacht or jet will need to catch a flight or ferry from St. Maarten).
Don’t be too intimidated if you’re not in the highest tax bracket, though: Swimsuits and sandals are the great equalizers, and that’s all most wear — though sometimes not even that much — to visit St. Barths’ 16 low-key beaches during the day. But you can’t keep poshness down for long, and at night, the dinners are elegant, the clubs are exclusive, and the yacht parties are legendary.
If you live in Bushwick, Greenpoint, Bed-Stuy, or Crown Heights
Then visit Cuba
Despite a couple years of legal travel to Cuba for U.S. citizens, the island nation still feels like a step back in time, with its parade of antique cars, grand buildings, and brand-new ability to access the internet via mobile phones. But it’s also something else now: a mashup of old and new. It’s a bohemian paradise steeped in art and innovation, and really what we’re trying to say is that Cuba’s galleries, restaurants, and coffee shops in alternative spaces, like an old cooking-oil factory, will seem to welcome North Brooklyn residents with open arms.
It’s the Caribbean island for culture-lovers who’d rather spend their days visiting galleries, exploring neighborhoods, and delving into literary history than beach-bumming it, though you can do that, too. And if you steer clear of the hotels, restaurants, and clubs set up for tourists, you’ll find it’s incredibly inexpensive there — something the cash-strapped artists and underpaid media workers in all these neighborhoods will want to put on their “pros” list.
If you live in Williamsburg, Dumbo, or Long Island City
Then visit Barbados
To destroy your social media followers with FOMO-inducing pics, go to the lush coral island of Barbados. New Yorkers from creative neighborhoods will love its sense of history and diverse influences, juxtaposed against the island’s startling natural beauty. Activities there run across the spectrum: You can visit a rum distillery, buy pottery from local artisans who are masters at their craft, or deep-dive into a centuries-old shipwreck on a scuba-diving adventure.
The island’s north coast is rugged, windswept, and uninhabited, though if you want more of a beach-day vibe, there’s plenty of that. The pink-and-white sand beaches are famously beautiful, and Barbados has some of the best surfing in the Caribbean. When you’re done, reward yourself at one of the island’s many rum shacks, where the liquor flows as freely as the reggae plays.
Having trouble deciding which island is right for you? Then a cruise just might be your best bet — letting you visit several islands in one trip. Find the right one for you through Royal Caribbean.
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