Christopher and Ashleigh share honest stories about their own travel missteps—so you don’t have to learn the hard way. This episode is packed with practical lessons, from booking blunders to overambitious itineraries, all with the goal of helping you plan smarter and travel happier. From wrong hotels in Manhattan to misaligned flights and rental cars in Puerto Rico, the hosts open up about mistakes that even seasoned travelers make—plus the simple systems and mindset shifts that help them recover (and sometimes even laugh about it later).