Family Vacations: An Exercise in Accepting Reality

I don’t love to admit this, but vacations are one element of parenting that I will sometimes lie about. When I tell friends or coworkers that I’m planning a family vacation or staycation, I feel somehow like I owe it to everyone to have an amazing time. After all, we’re lucky to be able to take time off–the last thing we want to do is complain about it. So, when I come back and everyone asks, “How was the trip?”, before I can even consider giving an honest response, I’ve already witnessed the word, “Wonderful!” leave my mouth. I can’t always bring myself to admit that after making plans, saving money, and taking time off, I’m absolutely exhausted and disappointed by the end. (I desperately wanted to amend that sentence to say “a little disappointed,” but I’m trying to be honest here, and the disappointment rarely feels “little”.) If I could manufacture magical experiences through sheer will, every vacation my family ever took would be perfect. That is, of course, impossible, but, with limited time and  finances, it feels like there’s an immense pressure to do just that (and the whole ‘you only get 18 summers’ thing did not really help things).

This may not resonate with you. If you are the super laid-back, take-it-as-it-comes type of person that I wish I was, you might read this and think, “good lord, this up-tight psycho needs to chill out.” And, you know what, hypothetical reader? You’re not wrong, but that’s not going to happen. So, how is a frequently anxious, Type-A-ish, people-pleaser who just wants everyone to have a magical time supposed to relax and enjoy vacation?

The answer is deceptively simple. Know yourself. Know your family. Who you are and how you are are not things to overcome, they’re things to lovingly factor into your plans.

“Vacation You” is still just you.
You’re going to be the same you whether you’re at home or in Rome, and this can be kind of a bummer until you learn to wield this knowledge like the glorious gift that it is. If I imagine myself vacationing in Rome, I’m suddenly thinner, cuter, wearing a perfect little black dress, smiling condescendingly at the other obvious tourists walking past my table as I sip the espresso I ordered in flawless Italian. Movies and social media have taught me to think that this is what a holiday experience should be. Except, guess what? I don’t like espresso, don’t speak Italian, would way rather in be comfortable clothes and a sports bra, love doing cheesy touristy stuff, and look how I look. Knowing these things about myself is actually helpful, because now instead of trying to emulate some version of what I think a vacation should be, I can plan a vacation that my family and I might actually enjoy. Where can we go that will be comfortable for everyone? Where will everyone feel included, safe, and free to have fun? If you’re kids are high-energy, loud, and boisterous, maybe don’t plan a week-long tour of America’s quietest libraries. If you hate humidity and reptiles, don’t trick yourself into thinking you’ll love the rainforest.

Over pack (if you want to).
If it’s going to help you to relax to know that you and your kids have an outfit for every possible weather event, do it. If you depend on your particular morning coffee to get your day started right, bring it. If you’re probably not going to start your period while you’re gone but there’s a slim chance you might, pack the appropriate supplies. Do what it takes to lighten some of that mental load before you even leave your house. Obviously if you’re flying or backpacking, you’re going to have to disregard this point, but, especially if you’re the parent that does most of the planning, if you think there’s something you might end up needing, pack it. Again, if you’re not a laid-back, ‘we’ll cross that bridge when we come it to it’ type person, don’t pretend to be! Own your control-freakishness and make a packing list!

Look for ways to say yes.
On vacation breaks, our kids have different rules. They can stay up later, they get to eat cereal (Lucky Charms is the current favorite), and when they ask to do something, I try to look for a way to say yes. My parents did this for my brother and I on family vacations when we were growing up, and simple things like getting to stay up late watching a movie or having a popsicle at 10am made a huge difference to us. We weren’t just along for our parents’ vacation, we were on vacation too! Normally, if my kiddos ask to have a s’more at 8:00pm on a Tuesday, the answer’s ‘no.’ But on vacation, it is probably a yes. Every family dynamic is different, but this is what we do, and we feel like everybody wins. The kids feel like they’re enjoying a very special moment in time, and mom and dad don’t have to be the constant rule-enforcers.

Do what you actually want to do.
Okay, so you’ve decided to do a beach trip. You’ve saved money, banked vacation time, packed up the car and have driven hours and hours to get to the beach—now you better make every moment count, right?! Everyone needs to be outside, laughing in the sun, swimming with dolphins every second of every day. Soak up every moment, or else. But what if you wake up late and want to do a puzzle? What if 2pm rolls around and everybody wants to take a nap? Try to give yourselves the freedom to do what you actually want to do instead of what you think you should want to do. Yes, you only have a finite number of days at the beach, but trying to force a ‘fun’ agenda or experience has pretty mediocre results, in my experience. Guilt ruins many a vacation—don’t let it get yours.

Try to catch the great moments as they’re happening.
Life is life, even on vacation. You’re going to have moments of bliss mixed in with temper tantrums, nights of little or weird sleep, and times you laugh so hard that your abs hurt. The whole spectrum’s always there, and it follows us anywhere we might go. But, the magical thing about vacation is that, hopefully, outside of your normal work-day routine, you’re a little freer to observe and appreciate what’s going on around you. Are your kids laughing hysterically as they fill their bathing suits up with sand? Is your partner smiling ear-to-ear because they’re out of an office and in the warm sun? Did you start happy hour at 3:30pm with a glass of wine you’ve been waiting to open? Put a mental anchor in at those moments; try to remember the sounds, smells, and sights. Try to make those moments vivid memories. You’ll come back to them.

Long story long, let the person that you actually are plan a vacation you and your family will enjoy. Not aspirational you, but regular you. If you want to post pictures of your vacations, of course, do it! But, also, you don’t have to.  Not publicly documenting a trip doesn’t make it less meaningful, and, sometimes, flipping through photos after-the-fact, trying to find the picture where I think I look the prettiest can cheapen the whole experience. I hope you have so much fun this summer, and I hope you do it while being your you-iest self. I’ll try too.


  1. My new go-to response to “how was vacation?” Is “there kids had a great time!”

    I feel more honest saying it, because they do have fun on vacation. And it avoids my truth, which is that we had some good family time, but it was exhausting, not rejuvenating, too expensive, and I have 1000 loads of laundry to catch up on.


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