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5 Caribbean Islands for the Perfect Labor Day Getaway 

downtown nassau

The Margaritaville Beach Resort in Nassau.

We’re just a few weeks away from the last holiday of the summer, and the people flocking to the northeast are forgetting our common refrain — the Caribbean is even better in the summer. What makes Labor Day different, of course, is that it’s typically just a long weekend, not a week or two-week-long getaway. That means a different region of the Caribbean, with an emphasis on shorter flights and quicker trips. 

So where do we recommend for your Labor Day vacation in the Caribbean?

Here are five great options, all of which are less than two hours from Miami and less than four hours from New York. 

the sexiest beaches including this resort at atlantis
Cove Beach at Atlantis Paradise Island.

Nassau, The Bahamas It’s always been the perfect weekend getaway from New York, thanks to its quick flight time, terrific resorts and abundant list of things to do. But in recent years, Nassau has gotten even better. Think world-class, chef-driven restaurants; a booming art scene; a vibrant cultural offering (one that includes the recently-transformed Queen’s Staircase); and a walkable, attraction-filled downtown. That only adds to what was already a fantastic beach destination (whether you’re in Paradise Island or anywhere on the north coast of New Providence) with an enviable collection of resorts, from large options like Atlantis Paradise Island and Baha Mar to lovely boutique stays such as the Graycliff Hotel and Restaurant and the sleek new Goldwynn. Flight time from Miami: 35 minutes. 

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The pool at the Shore Club in Turks and Caicos.

Providenciales, Turks and Caicos It’s no secret that the Turks and Caicos Islands has become one of the region’s true “it” destinations in the post-pandemic period, and that’s largely for two reasons: its world-class luxury resorts and its jaw-dropping beaches, centered around Grace Bay and Long Bay in Providenciales. Right now, we’re big fans of several Provo stops: the fabulous, ultra-luxe Shore Club on Long Bay, the perfectly-situated, family-friendly Regent Grand in the heart of Grace Bay Village and The Sands, one of the Caribbean’s classic beach resorts, right on Grace Bay Beach. Flight time from Miami: just under two hours. 

Grand Cayman A single day on Seven Mile Beach is better than a week just about anywhere else. Can you imagine an entire weekend? It’s no surprise, then, that the Cayman Islands’ most-popular destination is a perfect extended-weekend stop, from its buzzing dining scene (home to Eric Ripert’s only Caribbean restaurant, for one) to some of the best shopping in the Caribbean at Camana Bay. The island is also home to some great new hotels, from the sparkling Hotel Indigo, which just opened its doors, to the intimate, sustainable Vida Cayman Islands. Flight time from Miami: about an hour and a half.

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New beachfront bungalows at Cape Eleuthera.

Eleuthera, The Bahamas This island in the Out islands of The Bahamas has managed to cultivate a unique space in the Caribbean travel market: far off the beaten path, but still endlessly seductive. Eleuthera punches far above its weight, with a competitive Q score but a deliciously uncrowded feel. That’s in part due to its geography — it’s extremely long and sparsely populated, meaning it has a host of cool little corners and pockets. Right now, there are two particularly hot spots: Governor’s Harbour, known for its pink sand beach and a place that just welcomed its first nonstop flights on American Airlines; and South Eleuthera, which is home to the beloved Cape Eleuthera resort and has two major new golf resorts currently in development (including one that has Tiger Woods’ only short course in the Caribbean). Flight time from Miami: about 35 minutes. 

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The Teeth of the Dog golf course at Casa de Campo.

La Romana, Dominican Republic Maybe you know the Dominican Republic for Santo Domingo or Punta Cana. Think again. Tucked away in La Romana on the southern coast (just about an hour from the capital) is one of the Caribbean’s greatest resorts: Casa de Campo, a 7,000-acre self-contained destination that includes several hundred hotel rooms, hundreds of luxury, staffed villas, a beach club and some of the best golf in the world — anchored by Pete Dye’s legendary Teeth of the Dog course. Things got even more interesting of late when the resort debuted a stunning new spa, making it arguably the hottest destination for couples in the whole region right now. 
Flight time from Miami: about two hours. 


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