Decide When to Cruise – This step in planning can go hand-in-hand with destination planning because certain destinations are seasonal. For example, want to cruise Alaska? Well, Alaska cruises run from late-April to September, with the high season from June-August. Want to see the fall foliage in New England and Canada? Plan to travel between mid-to-late-September to October. Other seasonal cruises might include river cruises, Northern Lights cruises, Christmas Market cruises, just to name a few. Your personal schedule will also determine when you are available to go on a cruise. My family is still cruising during peak times because our son is in high school and that plays a big factor in our vacation planning decisions.