Pink Sands Beach in May

December through May gives you the best weather — dry, breezy, and temperatures in the low 80s. This is peak season, so expect higher prices and more crowds (though 'crowded' here means you might have to wait for a table at dinner). April and May are the sweet spot. Weather's still perfect, but rates start dropping as the season winds down. You'll have more of the beach to yourself, and the staff at restaurants and hotels aren't quite as stretched thin. Summer brings heat, humidity, and the possibility of hurricanes. But if you can handle the weather, you'll find better deals and an even more relaxed vibe. Hurricane season officially runs June through November, with September and October being the riskiest months. Winter months can get breezy — pack a light jacket for evenings. The trade winds that keep things comfortable during the day can make beachside dining chilly after sunset.