If you’re looking to plan a cruise, the cheapest cruise month will vary depending on the destination. High season for the Caribbean is November through April, so any tickets you can find in June through October will likely be cheaper. But remember, that’s hurricane season in the Caribbean. Cruises to Alaska, on the other hand, will be more expensive in May through September and less expensive (or not available) in the winter months. You can also find cheaper cruise deals if you avoid booking during school vacation dates or holidays.