Whether it’s due to historic architecture, compelling hotels or just plain smallness, certain Caribbean islands have an extra degree of charm. They’re places that enchant, places with soul. They’re the kinds of islands that seem ripped out of a storybook, islands with a bit of magic. And while you can find charming corners on almost every island in the Caribbean, these are the most charming islands in the Caribbean.
Barbados
Did Barbados invent Caribbean charm? Well, it’s certainly perfected it, with a special kind of luxurious elegance that somehow seems to pervade the whole island, whether you’re sipping Mount Gay at a beachfront rum shop or a table at Daphne’s. Most of the great boutique hotels here, particularly on the island’s storied Platinum Coast, tend to share a unique stone-meets-colonial architectural style, along with a focus on discreet, relaxed luxury.
Nevis
There’s just something lovely about tiny Nevis. The island is filled with charming small plantation inns, sugar mills, old churches, a quaint small capital (yes, where Alexander Hamilton was born) and an almost impossibly friendly vibe from its 12,000 inhabitants. This is the Caribbean as it once was, a calm spot that tugs at your heartstrings.
Harbour Island
The Bahamas’ capital of cool is a luxurious retreat where playful Caribbean pastels meet pink sand. This tiny place with less than 2,000 people is brimming with fashionable small hotels, from Valentine’s to the Dunmore and pretty whitewashed Old Bahamian villas.
Terre de Haut
The French know a thing or two about charm, and this is easily the French Caribbean’s most charming spot: the little fishing village-cum-island in the heart of the Guadeloupe archipelago called Terre-de-Haut. Think classic Creole architecture, small bars and restaurants, empty beaches and unlimited ti’ punches.
Bequia
The coolest place in the Grenadines is also its loveliest: Bequia, the funky island that seems to combine New England rustic-chic with a playful Caribbean personality. From its great little capital of Port Elizabeth to wonderful small inns and bed and breakfasts, this is a must-visit destination.
St Barth
You didn’t think we’d leave off St. Barth, did you? The jewel of the French Caribbean is the region’s capital of fashion, luxury and beauty, from its delightful capital of Gustavia to the red-roofed villas that dot the island’s green hills. It’s pristine, it’s elegant and it’s just about perfect.
St. John
One of the most beautiful islands in the Caribbean, this place is about the enchanting power of nature. And then there’s the robust art scene, which has turned the place into a Mecca for Caribbean artists and art-seekers. It all adds up to a kind of peculiar, but utterly pleasant island.
Anguilla
Yes, the story here is the beach, all 33 of them, to be exact. But this is a classic small island with classic small island charm, from its copious beach bars to chic, beautiful hotels designed not as large boxy megaresorts but thoughtful, artful places to stay.