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Top Caribbean Island Getaways

Winter is nearly here, but that doesn’t mean you need to bundle up and pack away your summer wardrobe.

All you need is a plane ticket to the Caribbean, some sand free beach towels, a good sunscreen, and you can make your summer vacation last a little bit longer.

With sun-drenched beaches, azure waters, and all-inclusive luxury resorts, the Caribbean is a tropical paradise you can explore on almost any budget.

Below, I’m breaking down some of my all-time favorite Caribbean destinations to help you whittle down the options and find the perfect location for your winter escape.

Top Caribbean Island Getaways

Ready to pack your bags and leave the plummeting temperatures at home? Here are some of the best Caribbean islands to visit, the top things to do, and which resorts deserve your booking.

Dominican Republic

Immerse yourself into nature with the Dominican Republic’s picture-perfect beaches, ultra-luxe resorts, and lush forests.

There is something for everyone here.

Whether you need lazy days with a cocktail in hand, bars with showstopping views, unique scenery, or a rich cultural heritage.

With so much to see, why not experience two of the island’s top resorts?

Azul Punta Cana is right on the beach and serves up tropical luxury at its finest. Feast to your heart’s content with inclusive gourmet cuisine, unwind at the spa, and take a dip in the sapphire blue water.

Margaritaville Island Reserve Cap Cana is a breathtaking resort in the Dominican Republic. With a grand opening special of 49% off, there’s no better time to experience what all the fuss is about. Located on a world-famous stretch of shoreline, Juanillo Beach, expect 5-star service and immersive culinary experiences.

If you feel like leaving the resort, here are some Dominican Republic attractions you don’t want to miss:

Isla Holbox, Mexico

Are you searching for an easy-to-reach Caribbean destination from the US? Look no further than Isla Holbox (pronounced hole-bosh).

Situated on the gorgeous Yucatan Peninsula and only three hours from Cancun, the small Mexican beach town is paradise incarnate.

Imagine streets paved with beach sand, no cars and the sound of traffic, and spectacular Caribbean sunsets. With this only scratching the surface of what Isla Holbox offers, it’s not surprising that the town is considered one of the most beautiful places in Mexico.

Struggling to decide where to stay? Check out St. Somewhere (opening soon!). With 39 sea-facing suites surrounded by Isla Holbox’s beauty and exciting activities like swimming with whale sharks, it’s perfect for travelers seeking refuge from the party towns of Cancun and Tulum.

Isla Holbox attractions worth adding to your itinerary:

St Kitts & Nevis

St Kitts and Nevis may hold the title for smallest country in the Americas, but don’t let its size fool you. The twin Caribbean island nation packs a punch with its breathtaking natural scenery, UNESCO World Heritage Sites, and world-class snorkeling spots.

While both islands deserve a visit, I’d like to focus on Nevis. Not only is it one of the top Caribbean destinations, but its moniker is “barefoot luxury.”

Sound like your type of vacation?

Between exploring the volcanic hot springs, wandering around the botanical gardens, and soaking up some Vitamin D on the beach, spend a night or three at the Four Seasons.

It’s a beachfront oasis with everything you need for an unforgettable luxurious Caribbean getaway.

Top things to do in St Kitts and Nevis:

St Lucia

With towering twin volcanic peaks, gushing waterfalls, lush rainforests, unspoiled beaches, and pristine reefs, St Lucia is the crown jewel of the Caribbean.

Not enough to lure you here for a week or two?

How about this: St Lucia is home to the world’s only drive-in volcano, Sulphur Springs.

Besides its plethora of spellbinding natural attractions, the island also offers luxury travel at its finest. Upmarket resorts sprinkle the coastline, including one of my all-time favorite romantic hideaways, Sugar Beach.

Part of the Viceroy Collection, you’re mere steps from the sparkling blue azure Caribbean waters and in total seclusion.

Top things to do in St Lucia:

Turks and Caicos

On the southeastern tip of the Bahamas, you’ll find one of the best Caribbean destinations – Turks and Caicos.

Home to a massive coral reef system, the island nation attracts snorkelers and divers from around the world who want to catch glimpses of the migrating humpback whales, tropical fish, and unspoiled coral reefs.

If water sports aren’t your thing, there’s plenty to see and do on land. Exquisite white-sand beaches from the 40 something islands, nature trails take you past dazzling sea views, iguana reserves, and underground caves.

The Islands are among the most sought-after tourist destinations in the world, due to their warm tropical climate, calm azure waters, and, above all, the best beaches. Additionally, the luxury Turks and Caicos villas might be able to offer you excellent fine dining options and endless activities as well. No matter what you end up adding to your itinerary, Turks and Caicos is the ultimate Caribbean retreat, especially if you’re a luxury traveller like myself.

When it comes down to deciding where to stay, I highly recommend The Shore Club. The exclusive resort sits on the sought-after stretch of Providenciales, Long Bay Beach, and it’s mere minutes from Provo’s town center.

In between exploring the Turks and Caicos, indulge in self-care at the on-site spa, cool off in one of four pools, and restaurant hop for lunch and dinner without leaving the resort.

Top things to do on Turks and Caicos.

Which of these top Caribbean destinations are you adding to your bucket list? Did I leave out any of your favorite Caribbean islands? Let me know in the comments below!