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Which Caribbean island should I visit? A very tough question indeed.

Barbados, Aruba, the Cayman Islands – you may already know the popular Caribbean destinations where millions flock to the sun-soaked shores annually, but they are just the beginning. Various paradise locations await every traveler, but with so many beautiful places to choose from, how can you know which island is the right one for your Caribbean vacation?

As crazy as it sounds, sometimes you have to think past the best Caribbean white-sand beaches (they are all going to be pretty gorgeous) and think about your budget, style, schedule, and the experiences you want to have that will last a lifetime.

After you do that, the rest is easy.

If You Don’t Have a Passport 

Forgot to renew your passport or did you apply too late? It doesn’t matter when you go to these Caribbean locations.

U.S. Virgin Islands 

Some of the best Caribbean beaches are here. Go to St. John, St. Thomas or St. Croix for an incredible vacation. Of course, since the U.S. Virgin Islands are a U.S. territory, you only need a birth certificate or government-issued ID to cross into this nirvana.


It may be a British territory, but it is passport-protected if your cruise starts and ends in the U.S. Then a birth certificate and government-issued ID is all you need to enjoy Bermuda on a closed-loop cruise getaway.  


With a closed-loop cruise, you can enjoy the ABC island of Curacao, an amazing mix of Creole, Asian, French, and of course, Dutch cultures.


Another option on a closed-loop cruise, Belize offers adventures in the rainforest and the awe-inspiring Mayan ruins make for an exciting trip.

P.S. Don’t forget about Puerto Rico. San Juan and Culebra are incredible getaways that rival many of the other options listed.

For Incredible Nightlife 

You did not travel to sit on the beach all day. Well, at least not a beach that doesn’t turn into a party.


Hopping clubs and bars, international DJ appearances, and reasonably priced cocktails and drinks make for fun nights here. Then there’s the beautiful beaches and architecture for the cherries on top.

Dominican Republic

Santo Domingo is the getaway for those who love buzzing dance clubs, every style of music, and live performances in hotels, bars, and nightclubs. Even the grocery stores (colmados) turn into locals’ favorite spots to grab a beer and listen to music.

No Caribbean Clichés Please 

There’s nothing in particular wrong with Caribbean clichés or paradise, but this trip, you just want something different. These islands may have what you’re looking for.


If the Dutch island’s population of 2,000 isn’t charming enough, the delicate Saba lace, handmade by the local women, will melt you completely. Another trip if you want to skip the beach, there’s a preserved marine park great for divers and Mount Scenery, the island’s highest point, offers spectacular views. You’ll also earn some bragging rights for knowing it exists.


You won’t find a ton of beaches and resorts around every turn. There are peaks and valleys covered in a rainforest with waterfalls accents.  


Escape the all-inclusive and mega-resorts and take off to this former British colony. Grenada’s capital, St. George is one of the more interesting cities to become acquainted with. It may be small, but the beautiful beaches are inviting and the hills of the rainforest will vie for your attention.

Sailrock peninsula blufs homesites

Onshore Adventure 

St. Lucia 

The twin peaks of Petit Piton and Gros Piton will take you through rainforests and scurrying over rocks to spectacular new heights.


English Harbour is where you can find Nelson’s Dockyard National Park and the British Naval Dockyard, a UNESCO World Heritage item, and some of the best nature trails in Antigua. A spectacle to behold, it includes restaurants, museums, shops, hotels, and a restored marina.

St. Kitts and Nevis

Sister islands that offer you golf courses, hiking, and history. Just big and interesting enough for a fantastic day trip, be sure to see the pirate-era landmark, Brimstone Hill Fortress.

Offshore Adventure

Being on the beach is fun, but water sports are just better.

Turks and Caicos

An ideal spot to roam the underwater world, you can kayak in the mangrove forests, explore one of the Caribbean’s longest barrier coral reefs at Grace Bay Beach or lay out on the dazzling white sand. Head to South Caicos for more world-class snorkeling in shallow waters and a little privacy.


Ambergris Caye is a must-visit for serious divers and the Belize Barrier Coral Reef is a sight to behold. It is the largest in the Western and Northern hemispheres.

The Cayman Islands 

Get more than up close and personal with some of the friendliest stingrays you’ve ever known. Stingray City, located on Grand Cayman is a once-in-a-lifetime experience like no other. Well actually, Stingray City in Antigua is also pretty amazing. Try them both!

Budget Savvy

You don’t have to return home wondering how you will survive without groceries. Beauty, relaxation, and a good time can be had at these affordable places.


Perfect for any budget, it is one of the most interesting places in the Southern Caribbean, has a fascinating history including the Salt Pyramids.

The British Virgin Islands 

Less-developed, richer, and more isolated than the U.S. version, you can find bliss here as well as options ranging from affordable to glam.


Because vacations are about living your absolute best life.

St. Bart 

The prices may be high but the quality you get is even higher on St. Barthelemy. A slice of Europe in the center of the Caribbean you’ll especially enjoy the food: French dishes with Creole flair.

Turks and Caicos

Accessible via boat only, Como Parrot Cay is the private island with a focus on wellness and luxury. You can rent Donna Karan’s Balinese-inspired sanctuary (yoga studio included) or one of the breezy villas that sit on the beachfront. It draws wellness seekers the world over.

The World Travel Awards recently named Sailrock Resort on South Caicos as the Leading Luxury Island Resort for 2020. Sailrock Resort is a secluded luxury resort with world-class authentic Caribbean dining and endless watersports activities.

turks caicos hobie cat sailing lesson

Ultimate Beach Bumming 


Flat, long and formed by limestone and coral, this island is filled with beaches of blinding white sand. There are a lot of luxurious ways to bum on the beach, too – exclusive mansions and a Four Seasons filled with sleek marble are just a few options.


If you’re not interested in travel whatsoever and lazing on the beach is the only thing that appeals to you, consider the French island of Guadeloupe. It has dazzling beaches, lots of tropical nature, and especially delicious cuisine.


Here, love is always in the air.

St. Lucia 

Lush rainforests, hot springs, and botanical gardens are everywhere. It’s no wonder this is the top destination for honeymooners.


Jamaica may not be the first place you think of for romance but it is one of the best. The Caves in Negril is one of the most romantic escapes. An intimate vibe and upscale amenities are set on a magnificent cliffside. There are only twelve cottages and children under 16 are not allowed.

With the Family 

The Bahamas 

One of the Caribbean’s most popular family destinations, The Bahamas is home to Atlantis Resort, private villas, and all-inclusive mega-resorts.

Get Ready for the Caribbean 

Never again wonder “which Caribbean island should I visit.” Though this truly amazing region has some of the best beaches in the world bursting with life, it has so much more.

From small, isolated islands and underwater caves to a huge party scene, it can never be overstated that the Caribbean has something for everyone.