The Travel Planning Mistake I Should’ve Known Better Than to Make

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Travel Planning Isn’t Always a Solo Job

When it comes to planning our travels, I usually take the lead. It’s not that my wife Sharon can’t do it—far from it. She once flew to North Carolina and surprised me on a business trip without me suspecting a thing. She’s more than capable.

It’s just that we’ve found our rhythm. I enjoy planning, and I know the ins and outs of using our points and miles. Sharon trusts me to handle the details, and I try to build itineraries that I know we’ll both enjoy. It’s a good system, especially after knowing each other for more than half our lives (which, yes, was a bit of a shock when we did the math).

Typically, I research our options and present a few solid choices, along with their pros and cons. I usually have a hunch about which one she’ll pick, but she manages to surprise me sometimes. That’s why I follow the process—because assumptions, even good ones, aren’t the same as actually asking.

Give and Take

Sharon gives me a lot of leeway. She didn’t question it when I said I wanted to fly Singapore Airlines from JFK to Germany, even though there were faster options. I made it worthwhile by renting a car, so we could drive around and look at the Christmas lights, and I added a stay at the TWA Hotel—give and take.

There was even a stretch during the pandemic when she took the reins. We weren’t flying, and instead of using points for hotel chains, we were staying in cabins and Airbnbs. She did the research, narrowed down the choices, and presented the short list. It was kind of refreshing to take the back seat for once, and all I had to do was pick the right credit card.

Now that travel has mostly gone back to the way it was before, I’ve resumed handling most of the logistics, especially when points and miles are involved. Booking for two people comes with its own set of complications, as anyone familiar with the “two-player mode” strategy can tell you. There are definite pros and cons to traveling on points and miles as a couple. Still, after falling back into my old routine, I made a mistake.

The Reminder I Needed

I was setting up a trip to Hawaii. Flights first, then hotels. I had carte blanche as long as I didn’t go overboard with routing. Everything was going smoothly—until I messed up the reservation dates for one of the hotels.

I found a replacement option that would cost 8,000 more Hyatt points per night but included club access and an ocean view. I hemmed and hawed. I ran through the justification out loud, as I usually do when I’m working through a tough call. That’s when Sharon said something that stopped me cold:

“You know, you haven’t asked me what I think.”

Touché.

“So, what do you think?”

“Book it!”

Just like that, decision made. I transferred points from Chase to Hyatt and locked in the reservation. And you know what? It was the right call. That stay ended up being one of the most memorable we’ve ever had.

Final Thought

If you’re the primary planner in your travel duo, don’t forget that you’re not the only one going on the trip. Even if your partner prefers to let you handle the research and booking, their opinion still matters, sometimes more than you realize. It’s not just about maximizing points or getting the best deal. It’s about making decisions together, so the trip feels like ours, not just yours.

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This post first appeared on Your Mileage May Vary