Some of the most expensive vacations I see aren’t the most luxurious ones — they’re the ones planned too late. Every year, travelers reach out just a few months before Christmas, Spring Break, or a milestone celebration, only to find higher prices and limited availability. And it’s not because travel has to be overpriced. It’s because timing matters. If you’ve ever wondered when you should actually start planning your vacation — especially if you want the best value, the best rooms, and the most flexibility — this is the conversation we need to have.