The Cayman Islands run deeper than their reputation suggests. Grand Cayman’s North Sound opens into mangrove channels and stingray shallows. Cayman Brac rises from the sea with cliff faces and caves that draw serious divers. Little Cayman sits almost entirely undisturbed, where the reef drops into some of the Caribbean’s finest walls just offshore. Our curators look for those who know these islands from the inside — the dive operator who has mapped every wall, the North Sound guide who grew up in the mangroves, the Caymanian cook keeping the old recipes alive.