The Vacation Mistake I Finally Stopped Making

For years, it's been eating away at my enjoyment.

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Published September 04, 2026
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Since I was a little kid, I have always been a planner. I like planning ahead, knowing the plan, making the plan, and having the plan.

My need to plan used to be especially intense when it came to vacations. From packing lists to places to go and where to eat, I was a planning machine. It wasn’t uncommon for me to start thinking and planning the next vacation on my way home.

But as I’ve gotten older, I’ve realized that one of the best parts of being on vacation is the unplanned moments. Overplanning was actually taking away from the experience and reducing my enjoyment.

Why Do We Overplan?

For some people, the ideal vacation is sightseeing in Spain. For others, it’s sipping tropical drinks with mini umbrellas on a beach. Regardless of the destination or activities, vacation is an opportunity to get away from home and take a break from “real” life.

But while the idea of a vacation is to relax and have fun, that may be easier said than done. “It’s natural to feel that a vacation needs to be ‘worth it’,” explains Dr. Gail Saltz, Associate Professor of Psychiatry at the NY Presbyterian Hospital Weill-Cornell School of Medicine and host of the How Can I Help? Podcast. “You're spending time and money, you're planning and anticipating, you want the vacation to be a ‘success,’ whatever that means to you.”

The desire for a successful trip is why people may overplan their vacations. As we get older, we may worry that we are running out of time to do the things we want. This feeling can be amplified on vacation. Saltz says, “With aging can come some anxiety. ‘What if I never come back here? I have to do everything because this may be my only chance.’”

Finding Balance

Most vacations do require some advance planning. Flights, accommodations, popular restaurants, and certain sights need to be booked ahead of time, or you risk something being sold out or not getting the best price because you booked late. “Planning ahead can make a trip a lot smoother,” says Melissa Nagelberg, owner of MN Signature Escapes.

But overplanning can have the opposite effect. “Trying to plan a ‘perfect’ vacation can be very stressful,” says Saltz. “Going into a trip with the mindset that it needs to be ‘perfect’ to be successful will probably result in disappointment. A goal of having a ‘good enough’ vacation, where you realize some things may go wrong but it will still be successful, is much more attainable.”

Limit The Must-Dos

“When a client tells me they have 10 days and want to see everything in Europe, I know I need to reset their expectations,” explains Shari Erasmus, travel expert and owner of Inspired Escapes. “The reality is, it’s not possible to see everything, and it’s certainly not fun to attempt to do so.”

In addition to being physically and emotionally exhausting, an overpacked agenda will lead to disappointment.

While planning creates a sense of control, the reality is it’s rare that a trip will go totally according to the plan. Flights get delayed, trains get canceled, lines are longer than anticipated, and the weather is unpredictable. Nagelberg says, “You want to plan a vacation with room for flexibility. Have your list of ‘must do’s’ but realize you may need to pivot from the original plan.”

Be Present

A packed agenda means moving from one thing to the next rather than immersing yourself in the experience. “When you plan a zillion things to do, it’s hard to absorb anything,” explains Saltz. “Instead of taking it in, your focus is on getting to the next thing.”

It can be less stressful and more meaningful to do less. Saltz says, “Rather than rushing on vacation, try to slow down. Take in the sights, smells, and sounds around you. Being present will create better memories than seeing everything just to check it off the list.”

Know Thyself

Getting out of your usual routine is an opportunity to see new sights, enjoy different activities, and try local cuisines that might not be available to you at home.

But keep in mind, you are still yourself on vacation. “Vacation can be exhausting," explains Nagelberg. “It’s important to plan a realistic trip that takes into account your fitness, mobility issues, and need for downtime.”

Be open to new experiences, but also true to yourself. “Just because everyone goes to the top of the Eiffel Tower doesn’t mean that you need to,” says Nagelberg. “It can take up a lot of your time and may not be worth the time and effort. For many, it’s actually more enjoyable and magical to watch the tower sparkling in the evening from a distance, away from the crowds.”

The Magic of The Unplanned

Perhaps the biggest problem with an overplanned vacation is that it doesn’t allow for spontaneity. Erasmus says, “You might get some great suggestions from a tour guide or a local you meet, and you want to allow time for those experiences. Some of the best vacation moments tend to happen off the beaten path, not online at a 'must-see' attraction.”

One of the most memorable moments of my recent trip to Italy was a simple lunch of pizza and Aperol spritzes overlooking the water. I don’t know whether the place was recommended by guidebooks or if it was the “best” view on the Amalfi Coast. It didn't matter — it was a perfect way to spend a vacation afternoon. And we only got to experience it because I allowed time for the possibilities rather than "planning" the perfect afternoon.

Do you tend to over-schedule yourself when on vacation? Let us know in the comments below.

Randi Mazzella is a freelance writer and journalist. Her work has appeared in numerous online and print publications The Washington Post, Next Avenue, Your Teen for Parents, SheKnows and New Jersey Family. She writes about a wide range of topics including parenting, mental health, wellness, pop-culture, teens, finance and midlife issues. She is a wife and mother of three children who inspire her every day. To read more of her work, go to randimazzella.com.