Don’t just assume that the weather in the Caribbean is gorgeous year-round. Hurricane season lasts from July through October and can put a major damper on your nuptials. If you're planning an outdoor wedding, be sure to have a Plan B. Check with your hotel or resort about their rainy weather plan and find out what you need to do on your end to reserve a last minute indoor option. It's the tropics, so expect passing showers even on clear, sunny days. Always have umbrellas nearby.