Now that Anguilla has been crowned the favorite new playground for spoiled celebrities, one would expect the pancake-flat island to be rife with exploitation. But Anguillans have fought hard to keep development to a minimum—perhaps too hard, as anyone who has braved the roads can attest. What business enterprise there is remains squarely under local control, and fiercely proud islanders won’t hesitate to let you know that your hotel belongs, in part, to them. The new 27-suite Ku (800-869-5827), a more affordable sibling to Cap Juluca, starts at $295 a night in mid-December.
In Bermuda, the locals are probably better off than you are—an offshore banking boom has made an already prosperous country even more so. And there’s a very British sense of pride and island history. By law, no chain restaurants are allowed, construction is tightly restricted (no building in the capital, Hamilton, can be taller than its Anglican cathedral), and Bermuda has the world’s oldest environmental-protection laws. Eschew the massive resorts for an intimate cottage colony like Ariel Sands (from $220; 441-236-1010) or the Reefs (from $294 December to March; 441-238-0222).
Unlike that other French island in the Caribbean, Terre-de-Haut doesn’t … strive. One of eight tiny islands that make up Les Saintes, it’s perfectly content to be itself, with brightly painted wooden houses, uncrowded beaches, and a casual vibe. The locals are secure with who they are and what they have to offer—in fact, they’re likely to pity us and our urban stress in a way only the French can. Auberge des Petits Saints (from $150; 590-590-99-50-99) and the Hôtel Bois Joli (from $220; 590-590-99-50-38) exude an enduring yesteryear charm at yesteryear prices.