6 Travel Mistakes I Keep Making (and always regret!)
read this before your next trip
I have a list of tried-and-true travel tips I share with my clients—little rules that make life easier and more pleasant on the road. But lately? I’ve caught myself breaking some of them. And every time, I end up regretting it.
If you’ve ever ignored your own good advice while traveling, you’ll probably relate to at least one of these. And yes, I saved the worst for last!
Discover the travel mistakes I make again and again - and the easy fixes to make your next trip smoother. Photo by Gary Lopeter, Unsplash
skipping the elastic pants on the plane
I have a travel uniform that makes prepping for trips so easy—comfortable, predictable, and always plane-approved. But every now and then, I think, “It’s just a short flight” or “I want to wear something cuter.”
Every. Single. Time. I regret it.
Jeans on a plane always sound better in theory. But the minute I sit down, I somehow gain five pounds, the waistband digs in, and I’m miserable for hours. No outfit is worth that. So take it from me—comfort wins every time when it comes to long flights or short hops.
Elastic pants are a necessity for every trip! Don’t get caught without them.
2. forgetting to refill my water bottle before boarding
This one hurts because I know better. My go-to airport hack is stopping by one of the Coca-Cola Freestyle machines to fill my reusable bottle with ice and cold water before a flight. That way, I have icy water both on the plane and when I land abroad.
When I forget? I end up with an empty bottle and nothing but warm, room-temp water waiting for me. It’s such a small thing, but trust me—hydration matters when you travel. If you’re not an ice person, skip that part, but never skip refilling.
3. leaving my detergent sheets at home
If you’re traveling for more than a week or two, laundry detergent sheets are a total game-changer. They’re compact, eco-friendly, and—unlike liquid or capsule detergents—they won’t leak or explode in your bag.
When I forget them, it’s always a hassle. I either end up hunting down a laundromat and overpaying for detergent from a vending machine or buying a huge bottle I’ll never finish. It’s not a big mistake, but it’s one of those little travel annoyances that’s easy to avoid.
4. forgetting a scarf or wrap for an extra layer
Does anyone actually like being cold? A scarf or wrap is one of the most versatile travel accessories you can bring. It works as a blanket on the plane, an extra layer in a chilly restaurant, or a cover-up for visiting churches or temples that require modest clothing.
Lately, I’ve been forgetting mine—and every time, I end up buying a new one on the road. The good news? My growing collection of scarves from around the world is lovely. The bad news? I could’ve saved money (and suitcase space) by just remembering to pack one.
5. forgetting slippers or flip flops for the hotel
You know that icky feeling when you realize you have to walk barefoot on a hotel room floor? I hate it. Yet somehow, I keep forgetting to pack my slip-on sandals or hotel slippers.
It’s such a small convenience, but it makes a huge difference—especially when you want to pop downstairs for coffee or ice without putting on real shoes. Since I live in my Birkenstocks at home, you’d think this would be second nature, but apparently not!
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6. the biggest travel mistake: skipping the insurance
This one makes me cringe — because I tell every client to buy travel insurance. Yet twice recently, I didn’t follow my own rule, and both times it came back to bite me.
The first time: I was heading to Napa for a short trip and thought, “It’s domestic, what could happen?” Four days, Delta flight, rental car (insured), all good — until I fell on the last day and broke my elbow. Thankfully, I was heading home anyway, but insurance would’ve covered the medical costs my health plan didn’t.
The second time: My husband and I had a dream trip planned to Croatia with friends. Everything was booked — hotels, transfers, tours — and I kept reminding myself, “Buy travel insurance!” But I didn’t.
Four days before departure, my mom fell and broke her shoulder. Instead of sipping wine on the Adriatic, I was in Vermont helping her through hospital stays and rehab. We had to cancel everything. Some hotels were refundable, others weren’t. I lost hundreds on prepaid tours that insurance would’ve covered.
The truth is, you can’t predict what will go wrong when you travel. Flights get canceled. People get sick. Strikes happen. Weather shifts. Entire countries pause operations.
Travel insurance doesn’t prevent the unexpected — it just protects you from losing money when it happens. Most of the time, you’ll never need it. But when you do? It’s worth every penny.
I’m finally learning my lesson — our next trip is to Panama, and yes, my policy is already purchased.
Even seasoned travelers slip up! From skipping the water refill to forgetting travel insurance, these are the lessons learned the hard way. Save this list before your next trip!
final thoughts
Even the most seasoned travelers make mistakes—I just happen to make mine in very repeatable fashion. The good news? Each one is fixable with a little preparation and a lot of humility.
So learn from me: wear the comfy pants, pack the scarf, refill your bottle, bring your slippers, and always, always buy the insurance.
And if you are planning a trip and want to avoid other mistakes, that’s where I come in! I’m here to use my experience, partnerships, and knowledge to help make a seamless vacation for you and your loved ones. You can learn more about what it’s like to work with me here.
Happy travels, friends!
Celebrate and Explore with ease!
