North America
Low-key luxury, powder-white sand and water in impossible shades of blue.
Anguilla is a flat, dry sliver of coral and limestone in the northern Leeward Islands, a British Overseas Territory with no cruise-ship crowds and some of the Caribbean's finest sand. Shoal Bay East, Meads Bay and Rendezvous Bay are long and uncrowded, and cliff-backed coves hide along the coast. Most visitors arrive by ferry or small plane from neighbouring St Martin.
The pace is slow and the food is the event: grilled crayfish and lobster at beach shacks, rum punch at Sandy Ground and a restaurant scene far bigger than the island. Boat racing is the national sport, peaking around the August Carnival. A hire car is the easiest way to explore. December to April is the dry, breezy peak; September and October bring the highest hurricane risk.
January, February, March, April, December.