Travel Mistakes We’ve Actually Made- And How to Avoid Them

Travel Mistakes We’ve Actually Made- And How to Avoid Them

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).

• Double-check hotel names and addresses—especially late at night or in cities with multiple locations of the same chain, as Christopher learned in Manhattan and Orlando.
• Keep flight, hotel, and rental car bookings in sync on a calendar to avoid gaps or overlaps—Ashleigh admits she’s booked too few nights more than once.
• Always consider free cancellation when booking accommodations, particularly during seasons with unpredictable weather. The hosts share how a snowstorm nearly cost them a Chicago hotel stay.
• Be wary of paying for upgrades you won’t use. Their “moderate” Disney resort splurge led to more walking, not more enjoyment.
• Don’t let budget flights with inconvenient connections or layovers—like their overnight detours through Chicago—ruin your trip’s value.
• Plan enough time in each destination; Ashleigh reflects on trips where moving too fast meant missing out on local food and experiences.
• Have enough local cash and consider travel insurance—especially when using budget airlines or booking non-refundable stays. The hosts recommend using insuremytrip.com as a helpful resource.

Mid-episode, Christopher introduces a cozy wine break: mulled wine using Cherry Wine (a semi-sweet wine from Good Harbor on Michigan’s Leelanau Peninsula) and their favorite mulling spices from the Spice House in Chicago—a small moment of comfort amid the chaos of travel stories.

Whether you’re a careful planner or a spontaneous explorer, you’ll find real, actionable advice in this episode. Listen in for relatable mishaps, practical fixes, and the kind of honest perspective that makes the Go See Do Explore Podcast a trusted travel companion.