GUIDES
Caribbean
Twenty years of sailing these islands taught me that the Caribbean isn’t one place. It’s a dozen different answers to the same question: which island feels like yours?
Where to Stay in the Caribbean
Start here. Most people pick an island by the prettiest photo, then wonder why it wasn’t the trip they wanted. This is how I’d choose one first.
Start Here →EXPLORE THE ISLANDS
Start with the island.
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Where to Stay in Anegada
Anegada isn’t just another island in the BVI, it’s the one even veterans look forward to.…
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Where to Stay in Anguilla
Anguilla doesn’t really have a bad beach, so the real question is where to stay. From…
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Where to Stay in Antigua
Antigua claims 365 beaches, one for every day of the year, and a sailing history that…
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Where to Stay in Dominica
Dominica isn’t a beach island, and it doesn’t pretend to be one. This is the Nature…
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Where to Stay in Jost Van Dyke
Jost Van Dyke isn’t a hotel destination, it’s a beach bar with an island wrapped around…
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Where to Stay in Nevis
Nevis is the island that makes you stop checking the time, the quietest stop in the…
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Where to Stay in St. Barths
St. Barths has a reputation it doesn’t need. From Gustavia to the quiet side at Toiny,…
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Where to Stay in St. Kitts
St. Kitts splits neatly in two: Frigate Bay’s beach strip and a rainforest interior most visitors…
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Where to Stay in St. Lucia
The Pitons decide most of St. Lucia’s story before you even arrive. Four areas, five hotels,…
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Where to Stay in St. Martin / Sint Maarten
I keep coming back to St. Martin, and not for the reasons the cruise ships do.…
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Where to Stay in Tortola
Tortola is the sailing capital of the British Virgin Islands, built around getting you on or…
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Where to Stay in Virgin Gorda
Virgin Gorda is my favorite island in the BVI, and I don’t say that about many…
More regions are coming. For now, the water is warmest here.