I'm Sorry, What?!

As travel professionals, we hear all kinds of questions—most are completely reasonable, but now and then we get asked something so out of left field it stops us in our tracks. While we’d never mock anyone (travel is complex and everyone starts somewhere), sometimes we just have to laugh. What follows is a lighthearted peek into some of the strangest, most amusing questions our industry colleagues have encountered. All in good fun—and all very real!

One client asked if we could block off the seat next to them on the plane so they could stretch out. Technically, yes—but it’s called buying a second ticket! Another asked if the beach at their resort would be “all sand.” We assume so... but mother nature likes to keep things interesting.

A favorite? The client who wanted two rooms in different parts of a resort—one for him and his wife, and another for his girlfriend. No, we didn’t ask follow-up questions, but yes, someone did later ask if their relationship with us was as confidential as attorney–client privilege. We’re guessing it was the same person.

One traveler sincerely wanted to get to Europe without flying or cruising. Unless you have wings or a sailboat and plenty of time, that’s a hard no. Another wanted to bring his mom along on the honeymoon. We quietly wished the bride good luck.

Then there are the cruise questions. Yes, the crew sleeps onboard—no, they’re not paddling behind in lifeboats. And yes, gambling is legal in the ship’s casino. No undercover sting ops here, we promise.

A sweet one: someone asked to avoid the window seat because they’d just had their hair done and didn’t want the wind to mess it up. (We loved this—she was flying to her granddaughter’s wedding and was absolutely precious.)

And then there’s the request that really takes the cake: “Can you watch my pet while I’m away?” We’re all for going above and beyond... but maybe not that far.

We share these stories not to poke fun, but to remind you that no question is truly off-limits—though some may earn a chuckle over cocktails at the next travel conference. So ask away... just don’t be surprised if you end up as a legendary tale in a travel agent’s next blog!