Your least-expensive airfare and hotel prices for the Caribbean occur during the off season when the fewest tourists visit. Avoid December through early April to save money and keep away from the crowds. Off-season sales begin in mid-April and extend through early December. From June through November, hurricanes are a threat, while mosquitoes are a problem to consider in the fall. But you'll find summery temperatures year round -- between 75 and 85 degrees Fahrenheit most days.
You can choose to travel during shoulder season -- the beginning and end of off season in late April and late November -- to take advantage of better weather and significantly lower prices than peak season. While you'll pay a bit more during shoulder season, you'll find that hotels offer more services than during the true off season, and more shops and activities will be available. You'll get the benefit of peak-season amenities and less rain at a fraction of the cost, although it will be more expensive than jetting away on cheaper hurricane-season dates.
Caribbean cruises have two peak seasons -- one boom for families traveling with kids during the summer and another when the northern United States and Canada are at their coldest. Avoid massive crowds and enjoy the fabulous weather by booking your cruise for late April or early May, or hold off till the kids are back in school and book between September and early December. If you plan to depart during harsh winter months, be prepared to fly out a day early to avoid delays due to weather.
Don't panic over excessive rates if you can only travel to the Caribbean during peak season. You can find deals that reduce the sticker shock of prime time by booking two to three months before your desired dates to secure the best fares available. Choose a destination with a high volume of daily flights, such as Puerto Rico, the Bahamas or the Dominican Republic. With more seats available, airfare prices are typically lower and the chance of upgrade is improved.
