It might help if you tell us where you are flying from, as DISers from your market are sure to have some good advice. In the MSP/St Paul area, flights to Orlando tend to be cheaper midweek (Tue, Wed Thur), although there can be exceptions to that. You generally can't book flights out for more than 11-12 months in advance, and some of the low cost carriers may offer only 6-8 months out. The end of January, your travel time, is generally a less travelled time. You are likely to get decent fares 2-3 months out from your trip. Sometimes booking way in advance is good too. In Oct 2004 I booked airfare to Seattle for our July 2005 cruise to Alaska and got very good fare that much in advance. Since you have a substantial amount of time before you travel, I would suggest watching the market by regularily checking fares (try Orbitz, and then check the carriers web sites as well). After awhile, you will be able to guage what is a good fare from your departing city, and you can learn what specials carriers offer and waht their flight schedules are. For example, I know in my market that the best fare I am going to get to MCO on Airtran is $84 pp one way, and that fare is darn good when looking at what other carriers in my area offer. So if I see that fare I will not hesitate to book it, no matter how far in advance my trip is. Once you determine what is good airfare, book.