Finding Your Perfect Caribbean Island – Part 1

(425 Reviews)
99% Recommended

Pam MacIntyre

Maple Grove, MN
Australia & New Zealand Specialist

New Zealand

In all my years as a Travel Professional, I’ve asked countless people, “What’s on your must-see list?” And without fail, New Zealand is always at the top! Honestly, who wouldn’t want to experience this majestic ...

Swimming with the pigs in The Bahamas

These Islands Are Just a Flight Away!


Looking for an easy escape to paradise? These stunning Caribbean islands are just a flight away from many U.S. airports—and each one has its own unique vibe, breathtaking beaches, and unforgettable experiences.


Aruba


Aruba is home to some of the cleanest, widest, and most beautiful beaches in the Caribbean. The locals are incredibly warm and welcoming, and the island is packed with things to do. Love adventure? Try world-class diving, windsurfing, or kite surfing (those trade winds are no joke!). Prefer nightlife? From beach BBQs and happy hours to cocktail lounges and karaoke bars, Aruba delivers.


It’s also one of the cleanest, most eco-conscious islands in the region—with low poverty rates and no beach vendors interrupting your zen. And if you enjoy casinos, there are plenty to explore.


Travel Tip: Grab some carrots or apples and stop by the Donkey Sanctuary—it’s a feel-good experience you won’t forget.


Dominican Republic


The Dominican Republic is the most visited destination in the Caribbean—welcoming around 6 million travelers each year. Punta Cana and Cap Cana serve up postcard-worthy beaches, and if you’re staying at Secrets Cap Cana Resort & Spa, you can literally walk two miles into the ocean with a cocktail in hand. Yes, really.


Want to see whales? Head to Samaná between December and March for a chance to witness humpbacks in their natural habitat. Whether you’re into laid-back sugarcane towns, lively fishing villages, or the colorful capital city, the DR has something for every kind of traveler.


Jamaica


Jamaica is laid-back, budget-friendly, and one of my personal favorites as a travel advisor. That said, where you stay really matters—it can make or break your experience. (Insider tip: it’s not the best island for cruise stops, as the port areas aren’t always the most scenic.)


But venture out a bit, and you’ll be rewarded. Negril’s Seven Mile Beach is absolutely stunning, and the lush mountains around Ocho Rios are perfect for nature lovers. Dreaming of an overwater bungalow? Jamaica has them—all-inclusive style! And if spicy food is your thing, jerk chicken is about to become your new obsession. 


Cayman Islands


Think: powdery sand, turquoise water, and unforgettable sunsets. The Cayman Islands are relaxed yet upscale, with the famous Seven Mile Beach as the star of the show. It’s also a foodie haven, offering everything from gourmet cuisine to delicious local eats.


Must-try bites: cracked conch and spicy conch chowder. You're welcome.


Puerto Rico


Old San Juan is as charming as it gets—cobblestone streets, pastel-painted buildings, and rich colonial history around every corner. Beaches near the city can be narrow or rocky, but if you're up for a little exploring, there are incredible stretches of sand just a short drive (or ferry) away.


History buffs will love Puerto Rico’s cultural landmarks, while beach lovers might prefer other islands for those perfect shorelines. A huge plus? No passport required for U.S. citizens. Just keep in mind—it’s often pricier than other Caribbean destinations.


Saint Martin (French) / Sint Maarten (Dutch)


This unique island offers the best of both worlds. The French side is quieter and more European in vibe, while the Dutch side (especially Philipsburg) is lively, with beach clubs, casinos, and shopping.


Many Americans lean toward the Dutch side, but no matter where you stay, you’ll enjoy stunning views and incredible food. If you’re a foodie, this island will steal your heart—many travelers come back again and again just to eat!


The Bahamas


With over 700 islands, the Bahamas offer everything from high-end luxury to rustic, off-the-beaten-path escapes. Want something iconic? Swimming with the pigs in Exuma is a must.


For unspoiled beauty, check out Emerald Bay, or head to Eleuthera and Harbour Island to walk barefoot along pink sand beaches. If you only see Nassau, you’re barely scratching the surface.


U.S. Virgin Islands


Renting a car here is easy, so exploring at your own pace is a breeze. The restaurant scene is thriving (especially during Dine VI in late fall), and outdoor adventure lovers will find plenty to keep them busy.


If shopping is your thing, the U.S. Virgin Islands offer the highest duty-free allowance in the Caribbean—with everything from artisan goods to high-end brands. Bonus history tip: make time to visit Blackbeard’s Castle!


So, which island is calling your name?


Whether you’re craving culture, cuisine, adventure, or pure relaxation, there’s a Caribbean island that’s just right for you. Let’s chat and find your perfect fit—your next great getaway is closer than you think!

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