Travel Advisor Corner: Travel Mistakes Smart People Make

One of my clients is the editor of a top U.S. metropolitan area newspaper. Wicked smart. Fast thinking. Super resourceful. Very well traveled.

But inevitably, when he volunteers to handle parts of his family vacation on his own, he winds up telling me horror stories of what happened.

Here are the most common travel mistakes we’ve seen smart people make.

Plan too late: A month before the holidays is no time to start making travel arrangements. While there may be the chance cancellation (and in some cases, great savings), the more common scenario is the client winds up overpaying for accommodations (“Only the penthouse is available”) and taking unpleasant connecting flights (four hours in the Miami airport) or worse, sitting in a back row seat in economy for an 8-hour flight.

• Book complicated flights for savings: Booking that inexpensive flight to and from Rome may at first seem to be a great savings. But how are you going to get to FCO by 7 a.m. if you are staying on the Amalfi Coast? Inevitably, we have to book airport hotels for these do-it-yourself bookings, bringing the price up and adding the inconvenience of another hotel check-in/check-out.

• Waste time shopping for best hotel deal: We’ve all had the client who got caught up in trying to find the cheapest price for their room. In the end, they may save $14 a night, but they’ve spent five evenings of their own time doing so.

• Go through security motions mindlessly: That moment of going through security is a vulnerable one. One in which you need to be on high alert at all times. All too often, travelers toss passports, phones and wallets in the security bins. Then they stand on line for the machine, get patted down and the next thing they know—no sign of their lose items.

• Take a taxi from the airport: While it’s cheaper to take a taxi from the airport to your hotel than have a driver meet you, the price one may pay in aggravation is just not worth it (and can more than double the fare). The rip-offs come in all varieties—the broken meter, the round-about route that doubles the time and distance, the language barrier resulting in the wrong hotel or the wrong side of town.

• Fall for free guides and other street “sales”: All over Prague, you see young adults (maybe students, maybe not) with signs that say “Free Tours.” Follow along and not only will you learn all sorts of fictional stories about the city, but in the end, feel obligated to give the self-proclaimed, non-licensed “tour guide” 5 or 10 Euros. Not a bad profit for an hour’s walk with 20 people.

• Not learning from mistakes: With all of the above experiences, you would think a smart traveler would change their ways. Not necessarily. Time tends to dull the memories and we’ve seen people time again make the same mistakes.

• Thinking they can do it all: Your clients may be able to do a lot of exceptional things themselves. Maybe they’re able to teach their kids the piano or build a treehouse that sleeps four. But the really smart ones are those who have figured out the best way to have things done right and in a timely fashion is to bring in the pros. Nowhere does this apply more than in organizing travel. Handle your client’s trip plans well and they’ll never be tempted to do it themselves again.

Susan Farewell is the owner of Farewell Travels LLC (, a travel design firm based in Westport, CT. Follow her on Twitter and Instagram @FarewellTravels.