The Caribbean island is one of the most hassle-free vacations you can take—no passport or adapters required, full phone and data service at no extra fee—and for that reason, it can get incredibly crowded. The holiday season gets particularly brutal, so go in early November, when crowds are low and it’s perfect beach weather. Here, you can eat like a king—opt for any of Jose Enrique’s famous restaurants, or follow the line of locals to a casual joint for a mallorca, a grilled ham, cheese, and egg sandwich covered in powdered sugar.