Round Hill Hotel and Villas

Ralph Lauren owns one of the villas here, and while it's off-limits, he did design the hotel lounge, which tells you most of what you need to know about the atmosphere. This Montego Bay resort holds a Michelin Key, and sits somewhere between old Caribbean money and effortless informality, with privately staffed villas, sea-facing suites, a quiet beach, and service formal enough to make you sit up slightly straighter.