The least clever AI prompt was the one that saved my trip

Reading Time: 4 min

I’ve been blown away by the clever AI prompts Points Path writers use to maximize their travel, from finding the best airport lounge access options to saving hundreds of dollars on family flights. In comparison, my trip-related conversations with Claude tend to be extremely basic — but as it turned out, that approach literally saved my latest trip.

Here’s how a pre-trip conversation uncovered a major blocker with my upcoming travel, and the prompt I reverse-engineered to prevent this from happening again.

I was debating the merits of several different checked luggage options for an upcoming Europe trip, using Claude as my sounding board. (I usually try to go the carry-on-only route, but the length of this trip demanded a step up.) After I settled on an option, I asked AI the following, almost as an afterthought:

What else do I need to do pre-trip?

Most of the items were no-brainers. Pack my travel gear a day or two before? Check. Break in new shoes so my feet don’t hurt on heavy walking days? Sure. But Claude also told me to do a 30-second passport check to confirm I had three months of validity past my return date.

… I did not.

I’m embarrassed to admit this, but I completely forgot that passport validity isn’t just a matter of the expiration date on your booklet! Depending on where you’re traveling, your passport may need to stay valid well past your trip: three months beyond your departure from the Schengen Area in Europe, six months in much of Asia, the Middle East, and Africa, and nothing beyond your stay for Canada, Mexico, or the U.K. My younger, more frequently jet-setting self would be ashamed.

My passport was expiring just about two months after my return flight from Germany, leaving me about one month short. Oh, and this was five days before leaving the country.

This wasn’t a small detail, because if you’re short, airlines can refuse boarding. I went into panic mode.

I was inside the 14-day window that qualifies you for an urgent travel appointment at a passport agency, and I got a slot for the following day.

A few hours and a frantic trip to CVS for a passport photo later, I was all set. It wasn’t cheap, especially with the expedited fee of $60 tacked on, but I was able to pick up my new passport the next day.

Working backwards, I worked with Claude to craft this prompt, which will henceforth be a staple of my pre-travel planning:

I'm traveling to [destination] from [origin], departing [date] and returning [date]. Don't help me optimize anything. List every document, enrollment, expiration date, or approval that could stop this trip from happening or cost me money at the airport — including the ones I've probably assumed are fine. For each one, tell me what to verify, where to verify it, and the last date I could still fix it if it turns out to be wrong.

The last line — with the cutoff date for fixing any problems — is especially useful. I recommend pairing this prompt with one that focuses on maximizing your credit cards or points and miles, so you’re attacking your trip from all sides.

While Claude saved the day by surfacing the passport validity problem in the first place, I didn’t leave anything up to chance. After making my appointment at travel.state.gov and filling out the renewal form, I relied on that website as my official source of information.

Claude didn’t get anything wrong. It told me to bring photocopies of my passport and license, and while the agent didn’t end up asking for them, the U.S. Department of State website does list photocopies of your citizenship evidence and photo ID as required — so bring them anyway.

But I wouldn’t count on AI as the final authority for anything like how many months of passport validity you need based on your destinations. It could have out-of-date or simply wrong information, so take the extra few minutes to confirm it with the official U.S. government website.

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