These 20 Caribbean Resorts Define the Barefoot Caribbean Vacation

Barefoot travel isn’t about the dress code. It’s a state of mind, and you usually feel it before you see it. It arrives in small, telling moments: the decision not to unpack fully because you won’t need much, the realization that your shoes are still by the door two days in, the way your schedule reshapes itself around light, tide, and appetite instead of plans. At the best barefoot Caribbean resorts, everything is effortless. The place does the work for you.

In the Caribbean, “barefoot” has never meant the same thing everywhere. On some islands, it’s literal: sand paths, salt air, the sound of the sea close enough to replace an alarm clock. On others, it’s more about mood than geography. You might be perched above the water, tucked into a garden, or a short walk from town, but the feeling holds. Life slows, choices simplify, and the day opens up. These are places where you’re encouraged to linger rather than optimize, where comfort comes from familiarity. 

The best barefoot resorts share a few unspoken rules. They respect the beach, even when they aren’t directly on it. They understand that food is part of the rhythm, not an event that needs staging. They leave space for silence, for conversation, for long stretches of doing very little. You won’t find rigid schedules or performative luxury here. What you will find are rooms that work, settings that invite you outside, and a sense that the island is leading the experience, not the other way around. Here are our 20 favorites for the perfect barefoot Caribbean vacation.

Les Îlets de la Plage, St Barth

On St Barth, where glamour tends to arrive first, this quiet stretch of sand does something else entirely. Les Îlets de la Plage feels residential in the best way, a small cluster of villas that open directly onto the beach. Days here move between swimming, walking, and lingering lunches, with the island’s energy close enough when you want it and far enough when you don’t. It’s St Barth for travelers who prefer salt air to scene, with a mix of lovely toes-in-the-sand bungalows and beautiful garden villas. 

Karen Udler

Karen Udler is the Deputy Travel Editor of Caribbean Journal. A graduate of Duke University, has been traveling across the Americas for three decades. First an expert on Latin American travel, Karen has been traveling with CJ for more than a decade. She likes to focus on wellness, luxury travel and food.