Some of the cheapest times of year to cruise are late winter and early fall. Rule of Thumb for Cheapest Times to CruiseWhile we believe that there are no bad times to take a cruise, certain weeks of the year are often cheaper than others. First two weeks of December – Sandwiched between the popular cruise weeks of Thanksgiving and Christmas, the first two weeks of December will often have great rates. Chart Showing Cheapest Cruise WeeksThis chart shows the average price of a 7-day to 14-day cruise throughout 2026. Cheapest Cruise to MexicoThe most inexpensive times to cruise to Mexico will be very similar to Caribbean cruises.