23-07-2025
I've visited 10 Caribbean islands since April — these are the places I'd go back to again and again
From floating beach bars to secret coves and tight-knit island communities, these Caribbean experiences are calling me back.
It started in April. A string of flights, ferries, and barefoot landings. In just a few months, I've touched down on 10 Caribbean islands. Some were new to me. Others were places I thought I knew, until I saw them differently this time. But out of the many piña coladas, passport stamps, and powder-soft beaches, there are a handful of places that grabbed hold of me.
This isn't a list of the best resorts of the most Instagrammed beaches. These are the places that felt different — that sparked joy, curiosity, and something a little more meaningful. If you're planning your. Next Caribbean trip and looking for something beyond the brochure, here are the places I'd go back to in a heartbeat.
1. The Floating Dock at Balaou — St. Martin
Let's start with one of the coolest experiences I've had all year: Balaou, a floating bar and restaurant just offshore in Grand Case. You call the restaurant, they send a dinghy to pick you up, and suddenly you're sipping a cold beer on a floating couch, surrounded by turquoise water and the hazy silhouette of St. Martin's green hills.
There's no elegant way to walk out ot your seat without wobbling, but that's part of the experience. Between the sunset views, the cheeky bartenders, and the fact that you're bobbing on a floating bar, Balaou is an experience you can't duplicate.
2. The Wild Cliffs of Middle Caicos — Turks and Caicos
Everyone raves about Grace Bay, and it's beautiful, don't get me wrong, but nothing prepared me for Mudjin Harbour on Middle Caicos. The cliffs, the crashing waves, and the tiny cay that looks like a dragon sleeping in the sea. I hadn't done much research before arriving, which made stumbling onto Dragon Cay Resort and its windswept trails feel even more surprising.
There's even a stone staircase that leads down to a hidden cave beach. The whole experience is raw, rugged, and so unlike the curated side of the Turks and Caicos most people know.
3. The Tight-Knit Vibes of Saba
Saba doesn't have a beach. What it does have is a ton of personality. This five-square-mile volcanic peak rising out of the sea is one of the most unique islands in the Caribbean. The roads are wild — switchbacks and cliff drops that make your palms sweat. But it's the on-island experiences that will be the reasons you come back.
In just a few days, I met the island's only glass jeweler, hiked the Mt. Scenery trail through cloud forest, and attended back-to-back happy hours with locals. If you're into diving, hiking, or just love the idea of an island that feels like a tiny town, Saba is for you.
4. Elvis' Beach Bar — Anguilla
I spent only an afternoon at Elvis' Beach Bar in Anguilla, but it was reason enough for me to find a way back to the island. The sand between my toes, the rum punch in hand, the faint sounds of soca in the background, and the slow glow over Sandy Ground.
The bar is made from a converted boat, the walls strewn with rusty license plates, knick-knacks, and other lost-and-found items that add to the bar's cobbled-together vibe. It feels like the definition of island time. Anguilla has its five-star side, but this is the side I fell in love with.
5. Cane Bay and the North Shore — St. Croix
St. Croix surprised me. Maybe it was the rotisserie chicken at La Reina, or the homemade mamajuana at Spratnet Beach bar, or the drive along the North Shore, with its horses, rum shacks, and wide-open views. But it's Cane Bay that keeps calling me back.
The beach here is low-key, with great snorkeling and diving just offshore. I had a local brew at The Landing, a shot of mamajuana with strangers, and conversations with everyone that gave me a different view of this lesser-visited U.S. Virgin Island.
6. Ti Kaye Resort — St. Lucia
There's no shortage of luxury in St. Lucia, but Ti Kaye Resort does something special. Perched on a cliff above a private bay, this adults-only hideaway is romantic, but also grounding. The cottages are tucked into the jungle, each with an outdoor shower and hammocks on the private porches.
The beach is reached via a cliffside funicular, a comprehensive wine cellar offers weekly tastings, and the resort prioritizes its commitment to its staff by providing subsidized medical care and education funding.
7. Starfish Alley — South Caicos
South Caicos only has two resorts, but that's not why I went. I was there for the back roads, the empty beaches, and a quiet little stretch of water the locals call Starfish Alley. The water is clear as glass, and the sandbanks are paved with actual starfish, which you'll see just by wading out knee-deep.
There's no official signage. It's just one of those places someone tells you about after you've had a couple rum punches and proven yourself curious enough to deserve the tip.
The Caribbean is not one-size-fits-all, and that's exactly why I am so eager to keep visiting. Each island has its own story to tell. While I've been lucky enough to visit 10 islands since April, it's these moments that stay with me the most.
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