Best time to go to the Caribbean

Caribbean season advantages and disadvantages
Peak Season
Advantages
Numerous sunny days and significantly less rain. Social season in full swing.
Disadvantages
Highest airline and resort prices. Flight and accommodation reservations go quickly - sometimes months in advance. Restaurants are packed.

Shoulder season
Advantages
Less expensive and crowded than during the peak season. Easier to make airline and resort bookings. Some tourist-oriented stores have major sales.
Disadvantages
Less likely to be blissfully sunny. Restaurants and nightspots less crowded, therefore has less vibrant social scene.

Low hurricane season
Advantages
Even lower costs. Scant crowds (great if that's your priority).
Disadvantages
Many restaurants, bars, and entertainment spots are partially empty, which negatively dampens the social ambiance. Some establishments curtail their hours or simply shutter their operations until December.

High hurricane season
Advantages
Lowest prices and easiest-to-get-reservations of the year.
Disadvantages
You're taking a big chance that a hurricane or major tropical storm won't ruin your vacation. And some tourist centers may seem like ghost towns.

Keep these Caribbean factors in mind
Chances of a direct hit
The Caribbean covers a huge area, much larger than most people think (look at a map). Even a monster hurricane is going to miss many islands.

Traditional hurricane belt
The hurricane path lies north of southerly islands like Aruba, Barbados, Bonaire, Curacao, and Trinidad, so visiting those islands during the hurricane season poses less risk.

Best side of an island during a hurricane
The effect of a hurricane or tropical storm is usually less pronounced on an island's Caribbean than Atlantic side. Take that into account when selecting a resort.

Tropical storms can also ruin vacations
Don't just be concerned about hurricanes. The number and severity of tropical storms increase during the hurricane season.