Royal Caribbean wraps up its cruise season in April or May, so if you can book a cruise, you'll find great deals. In addition, November is usually a month with less demand. This itinerary doesn't have a peak season after the high season because people also love to travel north in September and October to see how the leaves change color. So the cheapest times to do this itinerary are April, May and October.
By the end of October, the leaves are gone, and so are cruise ships by November. And most importantly, fly to the cruise port city the day BEFORE the cruise to avoid flight delays and not miss the ship. While the above tips are useful during normal hours or when booking a cruise well in advance, there are several factors to consider before booking a cruise right now. I think a cruise ship is a great vacation because it's an opportunity to get away from it all and have a place to relax.
Although some cruise lines offer Panama Canal cruises most of the year (they close only during the heat and humidity of August), demand goes back and forth during certain times of the year. Here's a great overview of several cruise lines, as well as a specific breakdown of cruise families. This is my favorite cruise site, as it seems to find all the deals and makes finding a cheap cruise easy. The real incentive is the heap of bonuses that cruise lines add to their promotions, making it difficult to stop booking a cruise (or three).
Another cruise destination with a short season is Canada and New England, with cruise ships visiting the ports of Rhode Island, Massachusetts, Maine and the maritime provinces of Canada. Cruising when schools are in session or during hurricane season will generally give you the lowest rates on Caribbean cruises. Planning a vacation during the pandemic can be tricky, and booking a cruise comes with an additional set of considerations and complications. But why not have both? Saving money on that Caribbean cruise (or any other cruise) is easier than you think: you just need to know how the industry works, including the best time to book a cruise, when you can get an upgrade, and how to get the trip you want without breaking the bank.
Cruises in Northern Europe and the Baltic have a shorter season, from May to early November, while the warmer Greek Islands and Canary Islands have cruises between March and December. The cruise season extends throughout the year, with departures from the West Coast of the United States (only one ship, NCL's Pride of America, operates seven-day Hawaii cruises to and from Honolulu).