Yes, the end of summer has unofficially arrived. Labor Day, celebrated on the first Monday of September, is seen as the last chance for travelers to enjoy the last rays of sunshine before the cold weather returns and kids go back to school.

So we have curated a collection of the 7 best Caribbean island destinations you can’t miss before autumn begins.

1. Eleuthera, The Bahamas


Cape Eleuthera Eleuthera

Eleuthera has gained tremendous popularity in recent years due to its unique features that set it apart from the rest of the Bahamas.

Although this island is also surrounded by laid-back resorts and luxury villa accommodations, Eleuthera, (freedom in Greek), invites you to explore, find yourself, engage in adventures, and connect with its friendly residents.

This place is also quite famous for its production of delicious pineapples, as well as its Queen’s Bath, which is a collection of soaking pools surrounded by rock formations.

Another treasure you can find in Eleuthera over Labor Weekend is its unique blue holes. These are some sort of cenote-like pools, rich in marine species and accessible by boat and ladders.

Fly from Miami to Eleuthera in only 35 minutes!

2. La Romana, the Dominican Republic

When you think of a weekend getaway in the Dominican Republic, you probably think of Punta Cana or Santo Domingo. We get it. It’s hard to explain why La Romana is not as famous as its above-mentioned peers.

In the past, La Romana was focused on sugar production. But now, it has transformed into one of the most luxurious beach destinations in the country, featuring cutting-edge restaurants and international shopping facilities.

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This place is best known for Casa de Campo, one of the most luxurious accommodations worldwide. The city is a great fit for golf lovers, as well as for those interested in carrying out businesses, conventions, and similar events.

Additionally, La Romana offers some of the most stunning beaches in the Caribbean, perfect for catching the final sun rays before the cold weather returns.

3. Nassau, the Bahamas


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It’s a fact. Americans love visiting the island of the Bahamas during Labor Day weekend. 

It not only boasts some of the best beaches in the region but is also “easy to reach from the major U.S. hubs.” 

This convenience explains why so many New Yorkers choose it as their summer send-off destination, according to Daniel Farrar, CEO of Switchfly, a travel solutions company. 

The most sought-after destinations in the Bahamas include Nassau, Grand Bahama, Eleuthera, Harbour Island and Great Exuma.

Nassau, in particular, (and we are not joking), has been praised by astronauts “as the most beautiful sight from space.”

It’s not hard to see why. Its white sand beaches, calm turquoise waters and top-tier restaurants, combined with a vibrant nightlife culture, international shopping and distinctive tropical vibe, make it an ideal hotspot to soak up the last summer rays.

4. Saint Barthélemy (St. Barts)


Eden Rock St Barthelemy
Source: Eden Rock Resort

St. Barts, a French Overseas Territory nestled between the Atlantic Ocean and the Caribbean Sea, boasts 14 stunning beaches surrounded by turquoise waters and abundant marine life.

What’s special about this place is that it feels like being in the French countryside but in the middle of the Caribbean, with its tropical culture, palatable cuisine and laid-back lifestyle. Strange, but very inviting..

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We recommend you visit the beaches of Corossol, Salines and Gouverneur for Instagram-worthy pictures and experiences you’ll never forget.

5. Crane Beach, Barbados


crane beach

Barbados is famous for its surfing opportunities, amazing beaches and, according to historians, for being the birthplace of Rum!

But if you decide to choose Barbados for your Labor Weekend Gateway, pay a visit to Crane Beach. You’ll be delighted by its pink and powder-soft sands and picturesque natural surroundings.

We are fans of this spot because it provides you with a more “private” experience, ideal for relaxation. The area is also perfect for sunbathing and swimming in warm, crystal-clear waters.

Although you may feel this is a secluded paradise, Crane Beach is actually in the parish of St. Philip, just 5 miles away from the airport.

6. Providenciales, Turks & Caicos


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Hands down, Providenciales is one of the most stunning islands in Turks and Caicos. Just imagine a place surrounded by water in every imaginable shade of blue—simply amazing!

This British Overseas Territory is considered a luxury destination. Therefore, it is not meant for all budgets.

However, visiting it during Labor Weekend could be your best decision. Being the low season, you can enjoy great prices and out-of-this-world beaches almost entirely to yourself.

Another advantage of visiting this time of the year is that it’s still in the dry season, so you will not see your weekend getaway ruined by unexpected rain.

Last but not least, Providenciales offers direct flights from New York, Philadelphia, Charlotte, Miami, Dallas, Atlanta, Toronto and London.

7. Grand Cayman, the Cayman Islands


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As one of the safest places in the Caribbean, Grand Cayman guarantees a relaxing escape to wrap up the summer on a high note.

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In case you are concerned about the heat, we’re glad to inform you that temperatures on this island remain relatively mild (80F to 90F / 27C to 32C), unlike nearby countries. 

Thus, you can comfortably engage in all types of exciting outdoor activities such as swimming, snorkeling, fishing and kayaking without too much trouble.

At this time of year, prices drop and crowds decrease, making Grand Cayman a dream luxury destination at an attractive price.

Our advice: don’t think twice and book your direct flight from Dallas, Atlanta, London, Miami, Los Angeles, Charlotte, Toronto, Denver, or New York City.

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