My Top Caribbean Destinations: 8 Islands I’ve Visited and Loved

The Caribbean is a treasure trove of islands, each with its own personality, flavors, and charm. While I haven’t explored them all (trust me, it’s on my list!), I’ve been lucky enough to visit some that left a lasting impression. From laid-back beaches to colorful towns and cultural gems, these are my top 8 Caribbean destinations (so far!), the ones I’ve personally visited and loved. Whether you’re planning your first island getaway or adding to your travel wish list, consider this your dose of sun-soaked inspiration.

1. Grand Cayman

I’m pretty sure I’ve visited Grand Cayman more than any other island, at least seven or eight times, between week-long stays and cruise stopovers. It’s one of those destinations that keeps pulling me back (and for good reason). It’s easy to see why Grand Cayman tops my list of Caribbean destinations.

Why It’s One of My Favorites

• Reliably gorgeous — From the soft white sand of Seven Mile Beach to hidden coves, Cayman just does tropical right.
• Easy logistics — It’s a quick 2.5-hour flight from Atlanta, so it feels almost within reach.
• Built for returns — Because there’s just that much here: water adventures, food, chill days, and more.

What I Always Do (and Recommend)

• Stingray City + snorkeling — A no-miss experience. Over the years, I’ve gone with different tours, but I keep coming back to the ones with smaller boats and more personalized attention.
• Seven Mile Beach — It’s iconic for a reason. I love just walking its length, stopping for a dip, and pausing for a sunset drink.
• Turtle Centre & “Hell” — The Turtle Centre is more than a “tourist stop” (there’s conservation and science behind it). And yes, sending a postcard from “Hell” is a cheesy but fun tradition.
• Eat like a local — Spots like Coconut Joe’s, Abacus, Rackam’s, and The Wharf are always on my list. Each trip I try to find something new to love.
• Explore beyond the beach — Pedro St. James, Smith Cove, Camana Bay — Cayman has hidden gems far from the sun lounger.

If you want more in-depth tips, photos, or pricing, I’ve already covered a lot of my Grand Cayman adventures in this blog post: Grand Cayman Island Getaway: Best Beaches & Local Finds

2. Curaçao

I fell in love with Curaçao the first time I set foot in Willemstad. Between the colorful Dutch architecture, laid-back Caribbean vibe, and some of the best beaches I’ve visited, this island quickly earned a spot on my top list. It is colorful, unique, and definitely deserves a spot among my top Caribbean destinations.

Why It’s One of My Favorites

• Unique blend of cultures — Dutch influence mixed with Caribbean warmth makes it stand out from other islands.
• Under-the-radar feel — It’s not as crowded or commercial as some neighbors, which gives it a more authentic vibe.
• Incredible beaches — The coastline is dotted with picture-perfect coves and clear turquoise water.
• Diver’s paradise — Reefs are just off shore, so snorkeling and diving are easy and accessible.

What I Always Do (and Recommend)

• Wander Willemstad — Punda and Otrobanda, plus crossing the floating Queen Emma Bridge, never gets old.
• Beach hop — Favorites include Cas Abao, Playa Kenepa, and Kleine Knip for that turquoise-water-meets-white-sand view.
• Snorkel or dive — You can literally step off the beach and find yourself in reef territory.
• Chase sunsets — The west side of the island has some of the best golden-hour views.

Want all the details on sand, surf, and hidden gems? I broke it down here: Best Beaches in Curaçao

3. Puerto Rico

Puerto Rico is one of the easiest Caribbean islands to get to, but it still feels like you’ve stepped into another world. With vibrant Old San Juan, lush rainforests, and beautiful beaches, it offers the perfect mix of city, culture, and nature.

Why It’s One of My Favorites

• No passport needed — For U.S. travelers, it’s as simple as booking a domestic flight.
• So much variety — From history to nightlife to natural wonders, there’s something for every kind of traveler.
• Old San Juan charm — Cobblestone streets, colorful buildings, and historic forts make it unforgettable.

What I Always Do (and Recommend)

• Explore Old San Juan — Walking tours, forts like El Morro, and plenty of time to just wander.
• Visit El Yunque — The only tropical rainforest in the U.S. National Forest System, with waterfalls and hiking trails.
• Sip a piña colada — The island claims it as its invention, and enjoying one in San Juan is a must.

4. St. Kitts

St. Kitts feels like one of the Caribbean’s best-kept secrets. It’s less commercial than some of its neighbors, but that’s exactly what makes it special. You get history, beauty, and a slower pace all wrapped into one and see why it’s one of my top Caribbean destinations.

Why It’s One of My Favorites

• Authentic vibe — It doesn’t feel overrun with tourists, which makes it more relaxed and genuine.
• Rich history — From sugar plantations to forts, you can feel the island’s past everywhere.
• Scenic beauty — Mountains meet the ocean here, making the views unforgettable.

What I Always Do (and Recommend)

• Tour Brimstone Hill Fortress — A UNESCO World Heritage site with sweeping views.
• Ride the scenic railway — A unique way to take in the island’s lush landscapes.
• Relax on the beach — South Friars Bay and Cockleshell Beach are two great spots to soak up the sun.

5. Aruba

Aruba has earned the nickname “One Happy Island” for a reason. With nearly constant sunshine, a mix of desert and beach landscapes, and plenty of things to do, it’s the kind of place that keeps you outdoors from sunrise to sunset.

Why It’s One of My Favorites

• Sunny and reliable — Aruba boasts year-round good weather, so you can count on sunshine.
• Unique landscape — Desert terrain, cacti, and rocky coasts give it a totally different vibe from lush islands.
• Friendly energy — The welcoming spirit really does match the island’s slogan.

What I Always Do (and Recommend)

• Relax at Eagle Beach — Famous for its soft sand and iconic divi-divi trees.
• Visit the natural pools & desert side — A rugged adventure that shows Aruba’s wilder side.
• See the flamingos — Renaissance Island is the spot for the perfect “flamingo on the beach” moment.

6. St. John

St. John may be small, but it’s packed with natural beauty. With two-thirds of the island protected as national parkland, it feels untouched compared to many other Caribbean destinations. It’s the kind of place that makes you want to slow down, unplug, and just soak it all in.

Why It’s One of My Favorites

• Unspoiled beauty — Lush landscapes and clear waters without the crowds.
• National park charm — Hiking trails, ruins, and beaches all within protected land.
• Laid-back pace — The island feels peaceful and slow, in the best way.

What I Always Do (and Recommend)

• Spend time at Trunk Bay — Famous for its white sand and underwater snorkeling trail.
• Snorkel at Maho Bay — Calm waters and a chance to spot sea turtles.
• Explore Virgin Islands National Park — Whether it’s a hike or visiting old plantation ruins, it’s always worth it.

7. Dominican Republic

The Dominican Republic is one of the most versatile islands in the Caribbean. Known for its beautiful beaches, lively resorts, and vibrant culture, it’s a place where you can choose to relax, explore, or do a little of both.

Why It’s One of My Favorites

• All-inclusive ease — Perfect for when you want everything at your fingertips.
• Beautiful coastline — Punta Cana and beyond offer miles of white sand and turquoise waters.
• Cultural flavor — Music, food, and history add richness to the resort experience.

What I Always Do (and Recommend)

• Relax in Punta Cana — Soft sand and crystal-clear water make it a classic choice.
• Take a boat to Saona Island — A day trip that feels like pure paradise.
• Enjoy the nightlife — From beach bars to dancing, the energy is infectious.

8. St. Lucia

St. Lucia is the definition of picture-perfect Caribbean. With the dramatic Pitons rising out of the sea, lush rainforest, and some of the most romantic resorts, it’s a destination that feels both adventurous and indulgent.

Why It’s One of My Favorites

• The Pitons — Those iconic twin peaks make the island unforgettable.
• Natural beauty — Rainforests, waterfalls, and volcanic beaches set it apart.
• Romantic vibe — Perfect for a couple’s getaway, but also fun for adventure seekers.

What I Always Do (and Recommend)

• Take in the views of the Pitons — Whether from a boat, a hike, or a resort balcony.
• Soak in Sulphur Springs — The world’s only drive-in volcano with natural hot springs.
• Relax on Sugar Beach — Nestled between the Pitons, it’s one of the most beautiful beaches I’ve ever seen.

Until the Next Island

These seven islands are my top Caribbean destinations so far, and I know I’ll keep adding to the list as I explore more of the region. Each one left me with memories I’ll never forget, from snorkeling with stingrays in Grand Cayman to wandering the colorful streets of Curaçao. What I love most about the Caribbean is how every island has its own personality, whether it’s laid-back, adventurous, or full of cultural charm.

Of course, my list will continue to grow as I visit new spots (always a good excuse to plan another trip!). For now, these seven are the ones that stole my heart and earned a permanent spot on my travel list.

Now it’s your turn. What’s your favorite Caribbean island, or which one is at the top of your bucket list?