I’ve Been To 15 Caribbean Islands — These Are the 8 I’d Return To And The 7 I’d Skip Despite Having Great Experiences

Some places call you back no matter how many times you visit. Others? Once is enough, even if the experience was incredible. 

After exploring 15 Caribbean islands, I know exactly which ones I’d return to without hesitation and which ones, despite their beauty, wouldn’t make my list again. 

Some had unbeatable beaches, others had culture and energy that pulled me in, yet a few just didn’t have that lasting spark. 

Ready to see where you should (and shouldn’t) go? Let’s get started!

1. Jamaica: Return For More

You need to see this place to believe it! The beaches are beautiful, and reggae music fills the air, making the place feel alive. 

The people are welcoming, and it feels like you’re right at home. Hiking through the Blue Mountains or trying the famous jerk chicken adds a bit of adventure to the mix. 

I love how there’s always something to do, and the sunsets are something else, they make everything feel calm and peaceful. I’d come back just to soak in that relaxed vibe. 

If you ask me, this is a place you shouldn’t miss!

2. Barbados: Skip But Sweet

Barbados was a nice escape. The calm beaches and gentle waves made it a great place to unwind. The rum was delicious, and the locals were incredibly friendly. 

It’s a perfect spot if you just want to relax and recharge. But for me, I crave a bit more excitement. While it was lovely, it doesn’t quite top my list of places I’d revisit. 

Do you agree with me, or would you give this place a chance?

3. St. Lucia: Return for its Pitons

Trust me, you don’t want to miss this. St. Lucia grabbed my attention from the start with the iconic Pitons, rising high from the sea. 

These volcanic spires create an unforgettable sight, with views that will stick with you long after you leave. 

Hiking the rainforest trails around the Pitons was a real highlight. The island’s natural beauty is one of a kind, making it a perfect spot if you love the outdoors. 

The warmth of the people and the lively culture make the island feel even more special. It’s a place I would definitely return to. If you ask me, take your time here, you’ll want to soak in every moment!

4. Trinidad: Skip but Skip for Carnival

Trinidad’s Carnival was an experience like no other.  The parades and costumes created a joyful atmosphere, filled with laughter and excitement. 

However, once the carnival ended, the island’s appeal seemed to fade. While the event was unforgettable, I found myself wanting more than just the temporary excitement.

Though I’ll always remember the carnival, I don’t feel the need to return unless there’s more to explore beyond the celebrations. 

Would you be ready for the carnival energy, or is there more you’d look for in a destination?

5. Grenada: Return for Spices

You deserve to experience a place like this at least once. Walking through the markets, I was surrounded by the aromas of fresh spices and the island’s surroundings.

The island’s connection to nutmeg and its other spices made it a perfect spot for anyone passionate about food. Learning about how these spices are produced added something special to my visit.

With its warm atmosphere and beautiful landscapes, Grenada is definitely a place I’d return to. The mix of culture and food makes it an experience that stays with you. I highly recommend adding this to your itinerary!

6. Dominica: Skip but Stunning Landscapes

Let me show you a hidden gem that most travelers overlook. The island’s green mountains and winding trails make it a great place to explore, with something new around every corner.

The waterfalls and forests felt untouched, but getting around wasn’t always easy. The island’s infrastructure made travel a bit frustrating at times, which took away from the experience.

It’s a place best suited for those who don’t mind roughing it for the sake of nature. Would you be up for the adventure?

7. Antigua: Return for Sailing

I dare you to look at this and not instantly add it to your bucket list! The calm harbors and steady winds make it a perfect place to set sail and explore.

Spending time on the water, discovering hidden coves, and feeling the open sea was an experience I won’t forget.

With its welcoming atmosphere and deep sailing culture, Antigua is a place I’d definitely return to. Whether you’re an experienced sailor or just looking for adventure, there’s always something new to discover here. If you love unique experiences, this one is for you!

8. Curacao: Skip but Colorful Architecture

Curacao’s colorful streets immediately catch the eye. The Dutch colonial buildings along the waterfront create a unique and lively setting.

Walking through Willemstad felt like stepping into a postcard. The mix of history and charm made for an interesting visit, but beyond the architecture, I found myself looking for more to do. The island’s attractions didn’t quite hold my interest for long.

While the buildings left a lasting impression, Curacao didn’t offer enough to make me want to return. What do you think? Do you agree with my opinion?

9. St. Kitts: Return for Scenic Railways

You’re about to fall in love with this destination. Riding the vintage train was a peaceful way to take in the island’s landscapes, with views stretching from green hills to the blue sea.

The steady rhythm of the train made the experience even more enjoyable. Each turn brought something new, from open fields to coastal cliffs. I’d return just to relive that slow, scenic ride and soak in the island’s beauty once more.

With its mix of history and stunning views, St. Kitts is a place worth visiting again. Would you take the ride and see where the tracks lead?

10. Aruba: Skip but Beaches

Okay, I have to ask, is there anyone who has never heard of this before? Aruba’s shores are a dream for anyone who loves the beach. The soft sand and clear waters made every moment by the sea feel like pure relaxation.

Spending days under the sun and floating in the gentle waves was exactly what I needed. But beyond the beaches, I found myself wanting more. 

The island didn’t offer much variety, and I kept looking for something new to explore.

While the beaches were unforgettable, Aruba didn’t have enough to make me want to return. It’s perfect for a laid-back getaway, but not a place I’d visit again.

11. Martinique: Return for French Flair

Pack your bags, this destination is calling your name. Martinique blends Caribbean energy with a touch of French charm.

Sitting in a café with a fresh pastry or strolling through lively markets filled with local flavors made every moment feel special. The mix of French and Caribbean influences created an atmosphere that kept me wanting to discover more. That alone is reason enough for me to return.

If you’re anything like me, you’ll fall in love with this spot instantly!

12. Bahamas: Skip but Snorkeling

The Bahamas is a haven for anyone who loves the ocean. Snorkeling through its clear waters felt like stepping into another world, surrounded by fish and coral in every direction.

Exploring the reefs was an unforgettable experience, but beyond that, I found myself searching for more. The island’s beauty is undeniable, but the variety of activities felt limited. That left me wondering if one visit was enough.

While the underwater sights were incredible, the Bahamas didn’t offer enough to bring me back. It’s perfect for a day of snorkeling, but not a destination I’d choose again. 

Do you think this location is worth visiting more than once?

13. St. Vincent: Return for Waterfalls

Take the leap and explore a place that will change the way you see the world. St. Vincent’s waterfalls are a sight to behold. 

Spending time near the waterfalls, I felt completely at ease, surrounded by the calming mist and natural beauty. Each waterfall had its own charm, inviting me to explore further.

With its landscapes, St. Vincent is a place I’d return to. The waterfalls and rich nature left a lasting impression, making it the perfect destination for anyone who loves the outdoors. 

This destination offers an experience that no other place can match.

14. Puerto Rico: Skip but Historical Sites

For lovers of the old times, this is the place for you. Walking through Old San Juan, I felt like I had stepped back in time, surrounded by colorful colonial buildings and rich stories of the past.

Exploring the museums and forts gave me a deeper understanding of the island’s heritage, but once I soaked in the history, I found myself wanting more. The island’s other attractions didn’t quite offer the same pull.

While I loved the historical journey, Puerto Rico didn’t have enough to bring me back for a second visit. It’s perfect for a day of exploring its past, but not much beyond that. 

Would you be satisfied with just the history, or do you need more variety from a destination?

15. Haiti: Return for Art

Let’s see if you can resist adding this to your bucket list. Haiti’s art scene is full of life and color. 

The colors and diverse styles pulled me in, offering a deeper connection to Haiti’s people and traditions. The art scene was truly a journey into the island’s soul, and it’s something I’d love to experience again.

With its artistic richness and welcoming atmosphere, Haiti is a place I’d gladly return to. The art and culture left a lasting impression, making it a destination worth revisiting. 

Personally, I think this might just be one of the best places I’ve ever seen!