We’ve all been there—that moment when you realize you’ve made a travel mistake that could have easily been avoided. After years of exploring everywhere from Manhattan to Mexico City, we’ve accumulated our fair share of blunders. The good news? We’ve learned from them, and now we’re sharing these lessons so you can skip the stress and get straight to the good parts of your trip.
Picture this: You’ve just landed at LaGuardia after a long flight, and you confidently direct your rideshare to your hotel. You walk in, reservation confirmation in hand, only to hear those dreaded words: “We don’t have a reservation under that name.”
This has happened to us not once, but twice—in both Manhattan and Orlando. The culprit? Hotel chains with multiple locations in the same city. In Manhattan alone, there were 11 Four Points by Sheraton properties. Our mistake was arriving late at night when we were exhausted and not double-checking the exact address.
The lesson: When you’re tired and arriving late, that’s precisely when you need to be extra careful. Add both your flight details and hotel reservations to your digital calendar, and verify the exact address before you get in that rideshare.
This might be the most common mistake in travel planning, and yes, we’ve done it multiple times. Whether it’s booking a hotel for one fewer night than your flights or mismatching your rental car return time with your ferry schedule (looking at you, Puerto Rico), date confusion can derail your trip.
The most dramatic example? We once booked a vacation rental and received a message asking what time we’d be checking out—a full day before we thought we were supposed to leave. Cue the scramble to find last-minute accommodations.
The solution: Put everything on your calendar. When you book flights, add them. When you book hotels, add them. When you book rental cars, add them. Then check it all again before you leave. Tools like TripIt can help keep everything organized in one place.
A few years ago, we had plans to visit Chicago in February (yes, we know—questionable timing). Two days before our trip, a massive snowstorm rolled through, dumping two feet of snow and canceling our Amtrak train. When we went to cancel our hotel, we discovered it didn’t have free cancellation.
Fortunately, because it was a major weather event, the hotel was understanding and didn’t charge us. But it could have gone very differently.
The takeaway: Always book with free cancellation, especially for winter travel or during hurricane season. If you choose a non-refundable rate for the savings, make sure you’re doing it intentionally and have trip insurance to back it up.
This one hits close to home. When you fly across an ocean, it’s tempting to try to see everything—Lisbon AND Porto AND that charming village you read about AND maybe we should add another city while we’re at it?
The result? Never enough time to eat at all the restaurants you’ve bookmarked, see everything you wanted to see, or simply soak in the atmosphere of a place.
The balance: While we haven’t completely solved this one (the travel planning excitement is real), being aware of it helps. Consider whether you’d rather see more places briefly or fewer places more deeply.
Our Disney World trip taught us this lesson the expensive way. We upgraded from a value resort to a moderate resort (Coronado Springs), thinking we’d enjoy the better amenities. The problem? We spent 95% of our waking hours in the parks and only returned to the hotel to sleep.
Not only did we not use any of the upgraded amenities, but the resort’s sprawling layout meant significantly more walking just to get from the bus stop to our room. And because it was far from Magic Kingdom—where we needed to be for the 50th anniversary—the commute was longer too.
The wisdom: Before paying for an upgrade, honestly assess whether you’ll actually use what you’re paying for. If you’re spending all day in theme parks, proximity matters more than a fancy pool.
Cheap flights with overnight layovers sound great in theory—save money and just sleep in an airport hotel, right? Wrong. At least for us.
We booked budget airline flights to Puerto Rico with overnight layovers in both directions. Between flight delays (looking at you, Frontier) and the time it takes to get from gate to hotel and back, we ended up with only a few hours of sleep, spending significant money on airport hotels we barely used, and arriving at our destination exhausted.
The better way: If you must do an overnight layover, look into Minute Suites—small rooms inside security that are less expensive than airport hotels. Or simply pay more for a direct flight or a layover that doesn’t require an overnight stay. The money you “save” often gets eaten up by hotel costs and the value of actually being rested on your trip.
GPS is amazing—until it tries to send you down a river. Literally. During a trip through Michigan’s Upper Peninsula, Google Maps suggested a “shortcut” between Marquette and Munising. What it didn’t tell us was that this “road” was actually an ORV trail that eventually turned into a river.
Our Kia Soul was not up for the challenge, and we had to carefully back out until we could turn around.
The reality check: GPS is a tool, not a gospel. Especially in remote areas, do a bit of advance research about road conditions. And if you’re driving in mountainous or rural areas (like Puerto Rico’s coffee country), consider renting a vehicle with higher clearance.
When you’re excited about a destination’s food scene, it’s easy to go overboard. Mexico City taught us this lesson when we planned three full meals out per day. After one particularly substantial Asturian/Spanish lunch, we couldn’t eat for 24 hours.
The sweet spot: In most places, planning one or two meals out per day works well. This leaves room for spontaneous street food discoveries, gives your wallet a break, and prevents you from being miserably full when you stumble upon an amazing taco stand at midnight.
Most of our souvenir regrets are minor—like the two crooked t-shirts we’ve somehow managed to buy. But the bigger lesson is about choosing quality over mass-produced items.
The better approach: Seek out locally made, handcrafted souvenirs that put money directly into local artisans’ hands rather than buying something that says the destination name but was made halfway around the world. And if you’re buying clothing, maybe try it on first to ensure it’s not crooked.
Despite living in an increasingly cashless world, cash still matters when traveling. We’ve found ourselves unable to buy tortas from cash-only vendors in Mexico City parks, struggling to tip service workers in Europe where card systems don’t allow gratuity add-ons, and hunting down change for laundromat machines at Canadian campgrounds.
The solution: Always have some local currency in small denominations. Don’t exchange money at your bank before traveling—just hit an ATM when you arrive for the best exchange rates. And keep a stash of small bills for tips, street food, and those unexpected cash-only moments.
This deserves its own section. Trip insurance isn’t just for cruise ships (though you should definitely have it for cruises). It’s for any trip where you have significant money at risk.
When we were stranded in Florida for two extra days due to a COVID outbreak at Jacksonville’s air traffic control, we had to take unplanned time off work and cover unexpected expenses. Trip insurance would have reimbursed us for those costs.
Critical advice: Never buy trip insurance from your travel provider. If the company goes out of business, your insurance goes with it. Use a third-party insurance marketplace like InsureMyTrip.com to compare policies and find coverage that fits your specific needs—whether that’s medical coverage, lost baggage protection, or trip interruption benefits.
Travel mistakes happen to everyone. The key is learning from them—either through your own experiences or, better yet, by learning from ours. Now get out there and make some better-informed travel decisions. And if you do make a mistake? Take a deep breath, fix what you can, and remember that sometimes the best travel stories come from the things that go wrong.
What travel mistakes have you made? We’d love to hear your stories and lessons learned.
Thanks for stopping by! Check out our Go See Do Explore Podcast, available wherever you listen to podcasts. To read about some of our previous trips, visit my Trips Page. If you like my photos be sure to “like” my Facebook Page and follow me on Instagram! For my list of gadgets to make your travels easier, click here.
