Nearly four years ago my fiancee and I went on our first cruise ever, a four night trip to the Western Caribbean in December that cost us approximately $300 per person (not including airfare). The cruise’s port of call was Miami and we were able to score cheap $70 tickets from BWI to Orlando, both were burgeoning Southwest hubs at the time. We were able to find such a screaming hot deal (a cruise for under a hundred bucks a day is pretty sweet) because we signed up for the cruise about a month before it set sail. It was one of those “Last Minute” deals on Travelocity (or Expedia or whoever, I forget which) and it was possibly only because we were keeping our eyes out for a last minute type vacation. However, with the great reward of a good deal comes a bit of risk.
Last minute deals are so great because they represent revenue that would otherwise be lost to the company offering it. The cruise ship will set sail with a full complement of crew and supplies regardless of the actual passenger count and an empty cabin represents a lot of lost revenue so selling it at a discount to the rack price is something they’re very much willing to do. It’s why hotels and airlines sometimes have last minute fares and discounts, an empty room or seat is lost revenue.
The flip side is the risk involved in waiting. If you really want to go on a cruise, say for your honeymoon, then you probably don’t want to risk waiting for a last minute deal because a last minute deal may never come. For example, we booked our honeymoon flights for Hawaii several months in advance when the deal looked good to us (it’ll run a little under $700 a piece from Baltimore to Honolulu, which seemed like a good price for the time we’re going); we weren’t willing to see if there was going to be a fare sale a month beforehand.
So, if you have a little flexibility, consider waiting until the “last minute,” roll the dice, and maybe you’ll go on a vacation you never expected – say to Iceland to ride some tiny horses and fight in the snow (I had a few friends do that, they have a blast). Many of the travel sites have “last minute” sections or you can always scour deal sites like Travelzoo  for great last minute bargains (I’m a fan of their Top 20 deals too).