8 Caribbean Islands I’d Happily Revisit + 7 I’d Skip (Even After Great Trips)
The Caribbean is an endless dream of sun, sea, and sand, and after visiting many of its islands, I’ve had the chance to discover some true gems—and a few that didn’t quite live up to the hype. While I’ve had great experiences everywhere I’ve been, some islands simply made a deeper impression on me than others.
In this list, I’ll share the eight Caribbean islands I’d happily revisit and seven that, despite wonderful trips, I’d skip next time. Let’s dive into my personal take on where to go and where to pass.
1. St. Lucia – Return for its Pitons and rainforest charm.
The islands where the sand feels like powdered sugar, and the water’s so blue it makes you wonder if it’s photoshopped. St. Lucia is one of those places. It’s not just the postcard-perfect beaches, but the mountains and the lush rainforest that make you feel like you’ve been transported to another world.
Every time I visit, it’s like I’m discovering something new—whether it’s scaling the Pitons or simply sipping a cocktail by the shore. There’s something about the vibe here that makes you forget everything else, leaving only relaxation behind.
2. Barbados – Return for the food and rhythm.
If flavor had a capital, it would live right here. Barbados brings spice, sweetness, and soca in one deliciously loud package.
From flying fish sandwiches to beachside karaoke, the energy is contagious. The island dances even when there’s no music playing, and somehow, you’ll find your hips joining in.
There’s no such thing as a boring night in Barbados—even a Tuesday feels like Carnival.
3. Dominican Republic – Return for the Combo of Mountains, Beaches, and Culture.
Some places just know how to multitask. One minute you’re hiking through pine forests in the mountains, and the next, you’re sipping coconut water on a sun-drenched beach.
The Dominican Republic doesn’t make you choose—it hands you the best of all worlds on a tropical platter. I’ve danced merengue in the street, explored old colonial towns, and devoured more plantains than I care to admit.
There’s history in the walls, rhythm in the air, and flavor in everything. Why settle for just one vibe when this place delivers the whole mixtape?
4. Antigua – Return for its 365 beaches (yes, one for each day).
They say there’s a beach for every day of the year, and I’m still trying to test that theory.
Antigua knows how to spoil you with variety—quiet coves, windsurfing spots, and water like liquid turquoise. It’s the kind of place where time moves slower and sunscreen runs faster. I never leave without a new favorite beach and a very uneven tan.
The real challenge is deciding which shore gets your towel next.
5. Grenada – Return for the spice and serenity.
You know you’re somewhere special when the scent of nutmeg hangs in the air like a welcome hug. Grenada is a sensory celebration—lush greenery, soft sands, and markets bursting with color. Even the fish seem friendlier here.
Every corner feels like a photo waiting to happen, especially when you’re lounging on Grand Anse Beach with zero intentions of moving. It’s laid-back, it’s lovely, and it leaves a sweet aftertaste.
6. Aruba – Return for its windswept beaches and consistent sunshine.
Forget checking the forecast—Aruba is basically set to permanent summer.
This island brings desert vibes, warm winds, and sunsets that deserve their own fan clubs. It’s not trying too hard, and that’s exactly the charm.
Whether you’re windsurfing or just watching lizards do yoga poses on the rocks, there’s always something oddly delightful happening. You arrive sweaty and leave sun-kissed with a suitcase full of memories.
7. Curaçao – Return for the colors and culture.
Take a box of crayons, spill them on a historic town, and you’ll get Willemstad. Curaçao is bold, bright, and buzzing with energy.
Street art and old Dutch buildings make every walk feel like a gallery tour. There’s soul in every corner—from the music to the markets.
And the diving? Like swimming through a dream. It’s where color comes to life and vacation gets a splash of extra fun.
8. Puerto Rico – Return for city thrills and rainforest chills.
One minute you’re salsa dancing in San Juan, the next you’re hiking through El Yunque. Puerto Rico doesn’t make you choose between city lights and nature vibes—you get both.
Add in mofongo, coffee that could wake the dead, and beaches that practically purr when you step on them. It’s a choose-your-own-adventure island with a rhythm that pulls you in.
There’s no jet lag, just jet joy.
9. Bahamas – Skip but pretty for a cruise stop.
It looks like a screensaver and kind of feels like one too.
The Bahamas delivers that classic tropical image, but it sometimes leans more “package tour” than personal escape. Great for a quick visit, maybe not for a deep dive. You’ll get your sun and sand, but if you’re chasing culture or wild experiences, you might find yourself drifting elsewhere.
Pretty? Yes. Profound? Not quite.
10. St. Thomas – Skip unless you’re into duty-free shopping.
Want shopping with a sea view? St. Thomas is your spot.
But once you’ve scored your perfumes and watches, the charm starts to fade. The beaches are lovely, but the cruise ship crowds can feel like rush hour in paradise.
It’s a decent day trip, though not the kind that lingers in your soul. Bring your wallet and maybe leave the big expectations behind.
11. St. Kitts – Skip unless you want peace and not much else.
There’s quiet, and then there’s St. Kitts. If you like a nap between naps and the sound of nothing at all, this might just work. It’s not buzzing with activities, but it does have sleepy charm and gentle waves.
The highlight might be the nap you took after your morning nap. Some call it boring, others call it bliss—depends on your travel mood.
12. Trinidad – Skip but skip for Carnival.
Trinidad outside of Carnival? Kind of like Disneyland with the lights off. But catch it at the right time, and it explodes with music, color, and energy that makes coffee jealous.
The rest of the year can feel a bit chaotic and less scenic than its Caribbean cousins. Still, that one wild week? Worth every glitter-filled second.
It’s a rollercoaster of culture and rhythm, one that leaves you breathless and begging for more.
13. Martinique – Skip if you’re not into French island flair.
Charming? Oui. But sometimes Martinique feels like Paris took a beach holiday and forgot to relax. It has elegance and fine cuisine, but can feel a bit stiff if you’re in flip-flops and chill mode.
For some, that fusion of France and Caribbean is just right. For others, it’s a little too croissant, not enough coconut.
But hey, if you’re in the mood for a sophisticated tropical getaway, this might just be the sweet spot you’re looking for.
14. St. Vincent – Skip unless you’re hardcore into hiking.
This island doesn’t roll out the red carpet—it hands you hiking boots. Rugged and raw, St. Vincent is ideal for adventurers but might leave beach bums confused. It’s not flashy, and it makes you work for the views.
If you like your islands wild and your legs sore, you’ll fit right in. If not, maybe wave from the boat. But for those who love a challenge and the beauty of untamed nature, this place is an absolute gem.
15. Bonaire – Skip unless diving is your love language.
Above the water? Kind of quiet. Below? A whole other world. Bonaire is a diver’s dream but doesn’t give much to land lovers. If snorkeling through coral forests makes your heart race, pack your fins.
Otherwise, it might feel like a scenic waiting room. Beautiful but niche—and unapologetically so.
For water enthusiasts, though, it’s paradise, and the vibrant underwater life more than makes up for the slow pace on land.