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I’ve planned more than 100 trips with my family. As the designated travel planner, I sometimes find it challenging to enjoy vacation.

August 13, 2025
in News
I’ve planned more than 100 trips with my family. As the designated travel planner, I sometimes find it challenging to enjoy vacation.
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The author and her family in front of a trolley to Valley Forge.
The author has planned over 100 trips for her family.

Courtesy of Kris Ann Valdez

“So, what’s next?” my 12-year-old asked as he sucked down his caramel milkshake.

It was only 10 am on a June morning in Georgetown, and we’d already had to stop to get a cold treat to rally the troops in the muggy 100-degree weather. As desert rats, we’re accustomed to a dry heat, not what felt like an insufferable, sweat-inducing sauna.

I looked from my son’s flushed face to the rest of my family, fanning themselves, and knew the itinerary that day — frolicking through Georgetown’s historic streets — was doomed.

There was a heat wave during our trip and we had to pivot our plans.

The author and her family on Elfreth's Alley.
Everyone agreed Elfreth’s Alley was worth the long walk.

Courtesy of Kris Ann Valdez

As the designated trip planner, everyone waited for me to make a decision, so I called an audible. My husband and his father would take the older kids to visit the Spy Museum, while my toddler, mother-in-law, and I stuck to the original sightseeing plan.

Thankfully, my well-researched itinerary kept everyone happy. I’ve planned more than 100 trips for my family, but I’m not sure they know just how much time and effort go into it.

A lot happens behind the scenes when booking a family trip.

The author and her family at the Philadelphia waterfront.
Everyone was in high spirits at the Philadelphia waterfront.

Courtesy of Kris Ann Valdez

For our eight-day trip to Washington, DC, and Philadelphia, I spent hours considering flight options, choosing an affordable hotel in a prime location, and strategizing whether or not we needed a car.

Parking in the city would be a pain, so I opted for public transport. But we wanted to take a day trip to Mount Vernon, and the bus route was rumored to be arduous. That’s when I found a ferry option from DC to Mount Vernon.

Next, I had to consider how to get from DC to Philadelphia. I decided to book the Amtrak train, but read that they didn’t allow larger suitcases to be stowed on that particular route.

I had to research a lot to make this trip happen.

The author and her family in front of a trolley.
A lot went into the group’s travel plans, including a trolley to Valley Forge.

Courtesy of Kris Ann Valdez

After some research, I found a company, Ship & Play, that would allow me to bring a full-size suitcase on the first leg of the trip and then ship it home directly from our first hotel, along with any purchases and half of our clothes.

And what about a car seat? No sense lugging one around only to be used once on the day trip we planned from Philadelphia to Valley Forge. With another search, I discovered a baby rental company called Babyquip that would let me rent a car seat for the Philly portion of our itinerary.

Then I researched activities, museums, and restaurants in each city. Which tickets needed to be pre-booked? What was our threshold for activities? How could I creatively include everyone’s “must-do’s”?

This research and fact-finding took days.

As the family trip planner, I feel responsible for everyone’s fun.

The author's family sitting on the Amtrak train.
The family was able to re-book their Amtrak train.

Courtesy of Kris Ann Valdez

Even then, things didn’t turn out the way we intended. Although the car seat rental, luggage shipment, and ferry ride went smoothly, the unexpected heat wave and a costly missed train ate at everyone’s patience. And since I’d booked the train, I was the one who shouldered most of the disappointment at missing it, and I was also the one to speak to Amtrak on an hour-long call to work out the logistics of rescheduling.

I realized this trip that I tend to take every grumble, sigh, and frustration as a personal slight. After all, I’m the one dragging them around and “making” them do things.

I’m grateful to be the planner and wouldn’t swap roles if I could.

The author in Georgetown wearing a black and white shirt and a hat.
The author is working on recognizing it’s not her fault when things go wrong on a vacation.

Courtesy of Kris Ann Valdez

Admittedly, the heat was miserable. We ended up ducking into multiple museums not on our original list just for the cooling A.C. All this museum hopping, coupled with the high temperatures, left everyone worn out.

When things go wrong, I often feel like I am either the creative problem solver or the scapegoat.

Still, I am grateful to be the elected planner.

On our next trip, I’ve resolved to try harder to shake off everyone’s grumpiest moments and release the guilt of feeling responsible for their fun. It’s not my fault when things go wrong; it’s just part of traveling.

The post I’ve planned more than 100 trips with my family. As the designated travel planner, I sometimes find it challenging to enjoy vacation. appeared first on Business Insider.

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