It’s something that horrifies travelers and you may have experienced it yourself. The vacation you’ve been saving and planning for all year is only a couple of weeks away. You’ve worked hard and you need a break from it all and you can’t wait to go to the beach and relax with fruity drinks with umbrella in hand and then you see… the same trip available for hundreds of dollars less than what you booked is a . You feel cheated, almost like you’ve missed something and in a way…you have.

So how come your friend, neighbor, or even that rowdy guy on the plane bragging about the great deal he got paid so much less than you? The answer in a nutshell is simple supply and demand. When tour operators send out their brochures, they usually have plane seats and hotels already ready for the upcoming season. They set their price point according to their markup and offer different incentives such as early booking bonuses, freebies or upgrades to sell these seats and rooms early. However, as the date of the trip approaches, instead of losing and letting the rooms and seats go empty, they reduce the price of the trip sometimes by several hundred dollars. Unfortunately for you, you opted for the free travel pillow when you booked in advance 4 months ago and missed out on the biggest savings. There’s nothing you can do about it, since once you booked, you’re locked into that price and the vacation is non-refundable (in the same way you can’t go to your stockbroker and say “I wanted to buy stock in Apple when it was cheap, can you adjust the price?”), but at least you have a travel pillow to cry on.

Playing the waiting game to book that last-minute vacation can be very rewarding, as the savings can earn you extra money to buy tours at your destination, a few more rounds of golf, upgrade your room, or even a few more nights out. Even more rewarding is the feeling that you won and now you can be the loudmouth on the plane or at the pool bar bragging about the great deal you got! Be careful though, there are risks involved and certain rules apply when trying to get a cheap last minute holiday. For starters, you have to be VERY flexible. The general rule of thumb is that if there is a certain resort that you need to be at by a certain date, then it is advisable to book early, secure your spot, and avoid all travel hype until you return. For example, if your best friend or family member has decided to get married at a resort and has chosen you as the best man or bridesmaid, you probably don’t want to wait just to save some money. The risk is that it will run out and end up costing you more to ship the ring to the Caribbean or Mexico while the rest of the bridal party is throwing drinks at the pool bar than it would have saved in the first place (Don’t laugh… Ha past). Other times you should avoid last-minute trips are the March holidays, Christmas, or any time there’s a carnival or big event. For the most part, these dates sell out early and you’ll be lying on your living room couch watching the Travel Channel instead of lying on a beach enjoying the scenery. If you plan to travel in a group, again, this is not a good idea, as there are often only a few seats left on the plane when the price drops to a minimum. Sure, the hotel says they have rooms available, but how are you going to get there if the flight is full?

So what if you just need a last minute flight from Toronto to Boston or somewhere charter airlines don’t fly to? Well, for the most part, you’re out of luck. Scheduled carriers generally work the opposite way in that the closer you get to the departure date, the more you pay. Just ask a business traveler who’s been called in to fly cross-country at the last minute how many great deals he’s gotten. That brings me to the next point; it also depends on the type of vacation you are looking for. Package tours (usually an all-inclusive resort with flight) are your best bet, as this makes up for most of a tour operator’s inventory and also represents more profit that they stand to lose if it doesn’t sell. Cruises offer big savings, but usually don’t include air, while escorted or guided coach tours don’t offer much, if any, last-minute savings.

So there you have it, a little background on last-minute travel and why and when you should do it, as well as some of the risks involved. If you have the flexibility and patience you can save a ton, but my last piece of advice is when you find a deal this good… Book it right away and lock in your price as you never know when it’s going to sell out. The other reason to grab it right away is that although tour operators can lower the price at any time, with supply and demand, they can also raise the price again and that can put you back on the plane seat next to you. guy bragging about the great deal he got. Do you still have that travel pillow?