Best Time to Cruise It's one of the most common cruising questions: When is the best time to cruise Alaska, Australia, the Caribbean, Canada/New England, Hawaii, Europe or the South Pacific? The answer depends on many variables. For example, fall foliage enthusiasts will find September and October the best time to cruise Canada/New England, whereas families prefer to sail in summer when temperatures are warmer for swimming. The best time to cruise to Alaska will vary depending on your preferences for viewing wildlife, fishing, bargain-shopping, sunshine, warm weather and catching the northern lights. For most cruise regions, there are periods of peak demand (high season), moderate demand (shoulder season) and low demand (low season), which is usually the cheapest time to cruise. High season is typically a mix of when the weather is best and popular travel periods (such as summer and school holidays). However, the best time to cruise weather-wise is usually not the cheapest time to cruise. The cheapest time to cruise is when most travelers don't want to go because of chillier temperatures or inopportune timing (too close to holidays, the start of school, etc.). But the lure of cheap fares and uncrowded ports might make you change your mind about what you consider the best time to cruise. As you plan your next cruise, you'll want to take into consideration the best and cheapest times to cruise and see what jibes with your vacation schedule. Here's a when-to-cruise guide for popular destinations.