If you're looking for a great vacation experience without the crowds, then early May or late August are the best times to go on a cruise. Airlines offer longer repositioning cruises in May and September, which can be great deals. December to February offer warm temperatures and the least amount of rain, making it the ideal time to take a Caribbean cruise. April or October are also great times to fly to a cruise port, as they offer good weather and low prices.
For the best weather in the Caribbean, December to April is the most pleasant time of year, as it is outside of hurricane season. If you're looking for deals, June, July and August are the most popular months for Caribbean cruises, and summer cruises have their own advantages and disadvantages. October to April is also a great time for Arctic cruises due to the Northern Lights. Finally, May is the driest month of the Alaska cruise season, making it ideal for wildlife viewing.