Planning vacations is one of my favorite things to do in my spare time. I genuinely love researching destinations, exploring places to stay and things to do, and figuring out an ideal itinerary. I try to farm out some of the planning to my family members, but they’re just not that into it.
Yes, I can be a “Type A” personality. Being a detailed planner comes in handy for this miles and points travel hobby. But, it can also be a hindrance.
Planning the “Perfect” Trip
As my family’s main trip planner, I deal with self-imposed pressure to get it right. I want to plan ahead so that we can get any reservations we need and not end up disappointed. Of course, social media and online trip boards add an extra layer of pressure. It’s easy to think we “have to” see certain places.
When my kids were younger, I remember planning a trip to Disney World. Our window for dining reservations just opened up, and the only time slot available at my desired character themed restaurant was like 3:30 p.m. That’s neither lunch nor dinner, so not ideal. As the trip got closer, I looked online and found an earlier lunch time slot. Perfect! Unfortunately, when I went to change the reservation, I got an error message and I lost not only the new time reservation but my original reservation as well. Now, we couldn’t even get into the restaurant at all.
I was so upset! I called Disney Dining, thinking they would at least reinstate my original reservation. Nope! I felt like I had just ruined my kids’ vacation.
Letting Go of Perfection
Now, looking back, it seems silly that I was so stressed and upset about a dining reservation. And the thing is, now I don’t even remember what restaurant it was! Maybe it’s because I’m getting older, or maybe it’s my anti-anxiety medicine, or both. But thankfully, I’ve evolved into a less-stressed vacation planner.
Last week, I realized just how far I’ve come. For our upcoming trip to Japan, I wanted to get tickets to Shibuya Sky, an observation deck above Shibuya Scramble. Many reviews say the best time to go is right before sunset, as the views are spectacular. Tickets go on sale 2 weeks prior at midnight Tokyo time and sell out quickly, according to my research.
Midnight Tokyo time is 10 a.m. at home. I would be unavailable at that time due to a work commitment, so I put my husband in charge of securing the tickets. I had him create an account, add a credit card, and get everything set up for a smooth transaction to get our ideal time slot at sunset or evening.
Well, the best laid plans….It turns out, in order to get the tickets, he had to enter passport information for all 6 of us. Say what?!?! And by the time he found the passports and got all of the info entered, the sunset and evening time slots had all disappeared. We “settled” on morning tickets.
My husband told me what happened, and he thought I’d be upset. But, I wasn’t. I’m chill about it. We still get to experience Shibuya Sky, even if it’s not at the “best” time of day. There are so many other cool things that we will experience in Japan.
I’m learning not to sweat the small stuff when it comes to trip planning. And of course, during the actual trip, I expect we will have hiccups. We always do. Hopefully, we can laugh about those hiccups someday.
Can anyone relate to this? Have you learned to let go of perfection when it comes to trip planning?

Author: Nancy
Nancy lives near Dallas, Texas, with her husband and three kids. Her favorite vacations include the beach, cruising and everything Disney.
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