If I weren't flying until 2006 (as indicated in your e-mail), I'd simply monitor prices for the time being unless a price shows up that is just to good to pass up on. The website travelocity.com has a low airfare search that automatically notifies you everytime there's an airfare price reduction to your designated cities. So, if the price to Orlando drops from $229 to $169, they e-mail you so that you can decide if you want to lock it in. As a result, you'll get an idea of what's a good fare and what's overpriced.
Usually, I find my best prices about 30 to 60 days from departure. I believe the reasoning is that it's at that point that the airlines want to start putting people in their seats and run a few airfare sales to get some seats occupied. Then, about 21 days out, they raise prices hoping to catch those business travelers. I guess the exception would be if you're flying around Christmas or other major holiday, then I'd book at least 60-90 days out.
The other benefit of waiting until 60 days prior to sailing is that you may cancel your cruise up to 60 days out, so if something happens and you need to cancel your cruise, then you're not locked into unrefundable airfare. In addition to travelocity, use bestfares.com. They have a search engine that shows you the best fares through surrounding airports too. For example, if you're preferred flight is Denver to Orlando, they also price Colorado Springs, Tampa and Daytona to see if there's a better fare. Bestfares.com also prices Southwest Airlines and other airlines that do not distribute tickets through other sites like travelocity, expedia, orbitz and other major engines.
I like booking my own air fare so that I can pick which airline, times and dates that I want, not what they choose for me. There are a couple of airlines that I won't fly on and that is one of my biggest reasons for booking myself. I like flying in the day before so that if something happens, like bad weather or flight delays, I'm not worried that we won't make it to port in time.
