My holiday is still a long time away (May 2013), but I'm already looking at prices for flights and rooms, and package deals etc. Now I'm wondering, is it smart to book something already when I see a good offer (which in most cases I cannot cancel anymore afterwards)? Or do I better wait until later, keep an eye on the prices and hope to find a better deal when closer to the actual time of travel? In other words: Do prizes always drop the closer it is to the actual date? Or is it more the opposite, the cheaper options will already be taken and you are stuck with the more expensive airplane seats and hotel rooms? Or is it neither and just the risk of the game? PS: I have already checked the convention calendar and it doesn't look like May is the time for conventions (the biggest one in the period of my holiday is a 3-day convention with 30.000 attendees).