The 10 Travel Mistakes I See Most Often (and How to Avoid Every One)

Bad trips aren’t bad luck. They’re bad preparation.

That’s the line that opens the back cover of my new book, How to Avoid the Most Common Travel Mistakes, 2027 Edition, and it’s the thing I believe most about travel. Almost every travel disaster I hear about, the missed connection, the frozen card, the insurance claim that got denied, traces back to one of a small number of mistakes that travelers make over and over. Experienced travelers make them too. Sometimes experienced travelers make them more, because what worked in 2019 doesn’t necessarily work now.

Here are the ten I see most often, and the fix for each.

1. Assuming last year’s entry rules still apply

Entry requirements have changed more in the last two years than in the decade before. The United Kingdom now requires an Electronic Travel Authorization (ETA) for most visa-free visitors, including Americans. Europe’s Entry/Exit System (EES) replaced passport stamps with a face photo and fingerprint scan at your first Schengen border. And the EU’s separate ETIAS authorization is still on the way.

The fix: Check your government’s official travel advisory site (travel.state.gov for Americans) about six weeks before you leave, then again a week before. Don’t rely on blogs, forums or AI chatbots for entry rules. They change too fast.

2. Forgetting the six-month passport rule

Your passport can be perfectly valid and still get you turned away. Many countries require at least six months of validity beyond your travel dates.

The fix: If your passport expires within six months of your return date, renew it before you book anything.

3. Booking the cheapest fare without reading what you bought

Basic economy is cheap for a reason. Travelers book it, their plans change, and they discover they’re out the full fare. The same goes for hotel rates booked through third-party sites, where the cancellation policy you see may not match the hotel’s own.

The fix: Read the fare rules and cancellation terms before you click confirm. If anything’s unclear on a hotel booking, call the hotel directly.

4. Building a connection that’s too tight

A 45-minute layover looks fine on a booking screen. In a sprawling hub, it can mean sprinting between terminals and watching your plane leave without you. And if your flights are on separate tickets, the second airline owes you nothing when the first one is late. (If you’re flying to meet a cruise, a missed connection can cost you the whole trip, because ships don’t wait. Fly in the day before.)

The fix: Scrutinize anything under an hour on a domestic connection or two hours on an international one. Keep connections on a single ticket whenever you can, so the airline is responsible for rebooking you.

5. Buying travel insurance that skips the part that matters

Plenty of travelers buy insurance that covers trip cancellation and assume they’re protected. The most financially significant coverage is medical evacuation, which can cost $50,000 to $200,000 or more depending on where you are.

The fix: Make sure your policy covers emergency medical evacuation, not just cancellation, and read the exclusions for pre-existing conditions and adventure activities. A good policy typically runs one to five percent of your trip cost.

6. Paying in dollars when the card machine offers

You’re abroad, you tap your card, and the machine asks whether you’d like to pay in US dollars. It sounds helpful. It’s not. It’s called dynamic currency conversion, and it uses the merchant’s exchange rate instead of your bank’s, which is often three to five percent worse.

The fix: Always choose the local currency, at card terminals and ATMs alike.

7. Packing irreplaceable things in checked luggage

Medications, electronics, important documents, jewelry. Every one of these turns a lost bag from an inconvenience into a trip-ruining problem.

The fix: If it can’t be replaced, or losing it would derail your trip, it goes in your carry-on. Make digital copies of your passport, insurance and confirmations, and store them somewhere you can reach from any device.

8. Arriving with no plan to get from the airport

You land tired, you’re in an unfamiliar place, and someone offers you a ride. Unofficial airport taxis are among the most common ways travelers get overcharged, or worse.

The fix: Research airport transportation before you fly. Know the official taxi rank, the train or bus option, and the regulated rideshare apps. Use official, metered options only.

9. Budgeting only for flights and hotels

The flight and the room are the easy numbers. Food, local transportation, entrance fees, tours and tips can come close to doubling the real cost of a trip.

The fix: Build a daily budget that includes all of those, plus an honest contingency fund. And keep a couple hundred dollars or euros of emergency cash somewhere separate from your wallet.

10. Leaving the last day to chance

Checkout time, baggage, getting to the airport. Too many trips end with the final hours spent in rushed, stressful problem-solving.

The fix: Plan your last day as deliberately as your first. Confirm checkout and transportation the day before, and know exactly where your bags will be between checkout and departure.

The pattern behind all ten

Look at that list again and you’ll notice something. None of these mistakes is about being unlucky or careless. They’re about information: knowing the right thing at the right time. That’s what the 2027 Edition of How to Avoid the Most Common Travel Mistakes is built to give you. It’s organized around the life of a trip, from booking and packing through flights, money, health, scams and the trip home, with a clear fix for every error. It ends with the 50 Golden Rules of Smart Travel to review before every trip.

The 2027 Edition arrives November 16. The Kindle edition is available for pre-order now, and the paperback launches the same day. See the book in our bookstore →

And if you’re already planning where to go, start with our city guides. Every one is built for travelers who want to arrive informed.