Anguilla

Anguilla is the Caribbean distilled to its essence. This flat, sun-bleached coral island — just sixteen miles long — has no rainforest, no volcanic peaks and no duty-free shopping strips. What it does have is thirty-three beaches of almost absurd perfection, water so clear it seems to have been digitally enhanced, and a deliberate resistance to the overdevelopment that has consumed so many of its neighbours. There are no cruise ship berths here. No high-rise hotels. No casinos. Anguilla made a conscious choice decades ago to pursue quality over volume, and the result is an island that feels genuinely exclusive without a trace of pretension.

The hotel portfolio reflects that philosophy. Four Seasons Resort and Residences anchors the western tip at Meads Bay, its beachfront villas and Barnes Bay suites setting a standard that few Caribbean properties can touch. Belmond Cap Juluca, draped along the crescent of Maundays Bay, remains one of the region's most recognisable silhouettes — those white Moorish domes against the turquoise sea. Aurora Anguilla, the island's newest arrival, has brought a fresh contemporary energy to Rendezvous Bay, while Malliouhana, perched on the bluff above Meads Bay, offers the kind of understated old-guard elegance that loyal guests have cherished since the 1980s.

Yet Anguilla's greatest luxury may be its informality. Lunch here means grilled crayfish at a beach shack with your feet in the sand and a rum punch in hand — Elvis's on Sandy Ground and Blanchard's Beach Shack on Meads Bay are island institutions. The local music scene, rooted in soca and reggae, spills out of bars on weekend nights with an energy that belies the island's tiny population. Hire a boat to Sandy Island, a sandbar with a single grill and a few sun loungers, and you'll understand why regulars call Anguilla the anti-St. Barts: all the beauty, none of the performance. If the Caribbean's glossier destinations leave you cold, Anguilla is almost certainly where you belong.