Oh, but you say, you are a travel professional, so you should know the trends and patterns. Well, the trends and patterns we can rely on are simply supply vs. demand. Demand is high during holidays and school vacations, so prices will be higher. Demand is lower in fall, and between Thanksgiving and Christmas, so prices will be lower. But if a volcano erupts, or there’s a political uprising, prices will probably drop no matter what time of year. But then you probably don’t want to go anyway, do you?
My point is, when you’ve decided that you are going to take a family vacation, and you have a pretty good idea of where you want to go, then book it! It’s fine to do some price-shopping, to see if it fits your budget. But once you see what you consider a “fair price,” don't agonize that you might save $50, $100, or even $500 by waiting for a better deal to come along. Because that later deal might not save you any money.
Case in point: A client booked an all-inclusive resort in Mexico in March, for travel in July. We found a good package, and in fact the vacation was less than he budgeted. Now in May, the resort is advertising a “Kids Free” promotion. So he contacted me and asked if he could switch to the new deal and save money. Well, it turned out that this "deal" would actually double the price of his vacation! If he had procrastinated in booking his trip, it would have cost him several thousand dollars more. (Yet he'd be proud of himself for having scored this "deal.")Another marketing ploy to be wary of is “special” or “exclusive” rates. They imply they are cheaper, but note that isn’t what they said. I once saw a popular internet travel site advertise their exclusive rates for a luxury resort on Maui. I checked it out, because our relationship with that resort was supposed to ensure nobody could offer a better value. It turns out the internet site did have a special rate: they were offering the rooms for $1/night more than the hotel’s regular rate! A little tweak in the rate, just so they could say it was "exclusive."
These stories support the two rules that I go by to get the best value: book earlier rather than later, and book through the right supplier, because travel companies are not all created equal. The reason I say “value” instead of “price” is that it’s not always about the money. You have to look at the whole package: can the supplier guarantee a USD rate for a European hotel, will you get first priority for a complimentary upgrade, are meals or spa treatments included?
It’s true, there are last minute “fire sales” when suppliers have unsold inventory, and they can be very, very good. But trust me, nobody is giving away travel for free! Also remember, you don’t get much choice in that situation. It’s like shopping at a “Going Out of Business” sale. If you don’t mind taking whatever’s left, you’re happy to go or stay anywhere if it’s cheap, then knock yourself out. But if you have an image of the “perfect” vacation for your family, do you really want to risk not getting what you want, or worse, get stuck paying more than you should have?