Five hard truths of vacation planning


Brace yourselves. Summer is coming.

That doesn’t sound very ominous and it shouldn’t be. Summer is very often the time of year when families go on vacation. Kids are off school. The sun is shining. It’s time to pack up and have fun.

Vacations, however, have a tendency to be expensive, and expensive things have a tendency to be stress-inducing, and before you know it, you’ve completely neglected to have any fun at all. Don’t let that be you. Vacations are hard to budget for, but if you’re smart and honest with yourself you can plan a vacation that fits your budget and leaves you with lasting, happy memories. Or at the very least doesn’t cause you to immediately disband your family.

But as I said, getting that plan together requires work and honesty. That means accepting and understanding the Five Hard Truths of Vacation Planning, which are as follows:


You can only have one priority

All other truths flow from this one. When it comes to planning, budgeting, experiencing, and enjoying your vacation, you have to accept that there can be only one true priority. There can be many goals, multiple ideals, infinite wishes…but at the end of the day, you can serve only one priority with complete satisfaction.

That means you must decide, early on, what the real priority of your vacation must be. If your top priority is saving money, so be it. If it’s having eating a lot of great food, so it shall be. If it’s taking one of those pictures where it looks like you’re holding up the Leaning Tower of Piza…that’s a reasonable priority as well, I suppose.

The point of this truth is that some priorities will be at odds with one another. Sometimes you’ll say your priority is X, but it’s really, secretly Y, and you’ll accidentally sabotage yourself trying to make these two conflicting priorities work out.

Pick one and live with it. It makes decision-making easier and helps you accept and adapt to any unforeseen occurrences that pop up.


Flexible and spontaneous are not the same thing

Going to the airport with a packed bag and no ticket can be one of two things – spontaneous or flexible. One’s expensive, the other can be pretty cheap if you play your cards right.

Being a spontaneous traveler is a romantic idea. You decide to go somewhere and then drop everything and do just that. If money’s not an object, go for it. At any rate, you’ll probably end up with a pretty good story. But if you’re reading this, most of the time money is in fact an object, so spontaneous probably isn’t your best play.

Flexible, on the other hand, is spontaneous’ slightly more pragmatic cousin. Being flexible means giving up choice in favor of discount. If you’re flexible you can catch great details on last second plane tickets, unsold hotel rooms, and everything else you need for a fun vacation. You just have to accept that the deals that pop up may not be for the kinds of things you had your heart set on. (In other words, don't set your heart on anything.) 

The right place at the wrong time is still wrong

Perfect moments are usually a combination of the right people in the right place at the right time. When you’re vacationing, you’re usually bringing the right people with you, and hopefully you’ve picked the right place, but that third element can be pretty elusive.

If you're completely set on where you're going to go, try to be a bit flexible about the when. If you don’t love crushingly crowded amusement parks, summer might not be the best time to visit some of the more popular destinations. Maybe you don’t really have a choice, but if you do, be sure to put a little strategy into when you go on vacation.


Check twice, book once

This should actually be Check six or seven times, then you can book. If you’ve booked a flight or a rental car or a hotel or a pontoon boat or basically anything in recent memory, you’ll know that there are a lot of travel websites out there. Rather than being put out by all the options, use that diversity to your advantage.

Check multiple sites to see what offers are available. Play with the dates. You’re going to get a lot of different numbers. That’s good. Pick the best one. You win! (For a more detailed examination of how you can use multiple travel sites to your advantage, check out this article from the New York Times.)


Fun is what you make of it

Finally, just remember that ultimately you’re the only one who decides whether or not your vacation is going to be any fun. That’s hard to remember when things don’t quite go the way you want them to and your toddler is crying or your teenager is sulking, but it really is true.

As soon as you stop planning your vacation and start living it, a lot of things – almost all of them, in fact – are going to be out of your control. All you can do is accept that. And then you have to decide if you’re going to roll with all the unexpected setbacks or if you going to let yourself have a rotten time.

No matter what, if you’re going on vacation this summer it will probably be memorable. You have the power to make those memories good ones. It just takes time, thought, honesty, and a good attitude. Good luck!

Jesse Campbell photo.

Jesse Campbell is the Content Manager at MMI, with over ten years of experience creating valuable educational materials that help families through everyday and extraordinary financial challenges.

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