I Forgot The Most Important Thing When Booking A Trip For A Couple

by joeheg

When it comes to travel planning, I do most of the work. Don’t misunderstand; Sharon’s fully capable of making plans for herself, as she proved when she flew to NC to surprise me during one of my business trips.

It’s more of a mutual decision as she knows that I enjoy doing the planning and I know more about the options we have with our points and miles. We’ve known each other for more than half our lives (what a shocker that was when we did the math!), so I have a degree of certainty about what Sharon’s going to say when I present travel plans.

Once I’ve completed the initial searches, I usually provide multiple options with their respective advantages and disadvantages. Although I may have a hunch about which one she’ll choose, sometimes she surprises me. That’s why I always follow the process, as I understand that my assumptions may not always be accurate.

Sharon makes it easier by giving me leeway with the plans. For instance, she didn’t bat an eye when I said I wanted to fly to Germany on Singapore Airlines from JFK when there were faster options. I built things into the trip that made it more palatable for her, like renting a car so we could drive around and look at Christmas lights for an evening, and a stay at the TWA Hotel. Give and take.

a plane parked next to a luggage cartSharon took a larger role in planning our trips during the pandemic, when our travels shifted to road trips and staying at Airbnb. She did the research about the different places, distilling the choices down to a few that met our needs.  I’m not going to lie; it was kinda nice. Since we weren’t using points to pay for the cabins and condos, the only thing I needed to worry about was making sure we used the correct credit card.

Now that things are back to relative normalcy, I’m back to doing the planning. When booking trips for two people using points and miles, there are some advantages and challenges you don’t have when only booking for one person. It’s how things are when you’re using two-player mode. But when I was getting back to planning our trips, I forgot the most important thing when planning trips as a couple.

I followed my usual process when setting up our trip to Hawaii. The first thing was to decide on the dates for the trip. The next step was booking flights, for which Sharon gave me carte blanche, as long as I didn’t get too crazy with the routing.

Once I had the flights, it was on to the hotels. The first big decision came after I messed up our reservation at the Grand Hyatt Kauai and booked for the wrong dates. I could re-book a room with club access and an ocean view, but it would cost 8,000 more points a night.

a view of a golf course from a window

View from our balcony at the Grand Hyatt Kauai

I’m bad at making decisions, so I’ll work through options by talking it over with Sharon. That forces me to think about the decision at hand. Sharon stopped me after going over why I wanted to book the club room and why I thought it was too much to spend on a reservation.

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

Me: “Uhhhhh”

Yeah, I totally left her out of the process.

Me: “So, what do you think?”

Sharon: “Book it!”

That was easy. When I got back to my computer, I transferred the necessary points from Chase to Hyatt and booked the club room. Looking back, it was the right decision as that stay at the Grand Hyatt Kauai was one of the most memorable hotels we’ve ever visited.

Here’s a little advice if you’re the one who makes the travel plans. Don’t forget that you’re not the only one going on the trip. Even though the others are not as involved in the plans, they need to have input into what’s going to happen.

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This post first appeared on Your Mileage May Vary


Gene January 7, 2024 - 2:50 pm

@ Joe — I guessed the answer was two plane tickets (versus one).

Billy Bob January 7, 2024 - 5:54 pm

Happened to me too: forgot the wife. Oops.


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