Using the ‘$20 Rule’ to De-Stress Your Next Family Trip

Mar 18, 2019

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The “$20 rule” has historically been a travel tip used to score upgrades at hotels. Supposedly, as you pass over your credit card and ID when checking in, you slip a $20 bill between the cards and oh-so-casually ask if there are any upgrades available. While I’m skeptical that this $20 rule works all that frequently, there’s no denying that people still like to try it. Personally, I prefer to get my upgrades for free, either through hotel status or by emailing the hotel beforehand to try and snag a larger suite.

Today though, I want to share a different $20 rule — one whose adoption has resulted in a major de-stressing of our family’s vacations.

Using the $20 Rule to De-Stress Your Family’s Vacation

Here’s the $20 rule that our family uses to keep stress low while traveling:

If there’s anything that you can do to make things easier, or have things go smoother, that costs $20 or less, just do it.

I’ve been (rightfully) accused of being a cheapskate (I prefer the term “frugal.”) But after 40+ years, I am trying to get better at this — especially while on vacation. Beyond that, as a family of eight, keeping things on budget is extra important and we’re always looking for ways to keep costs down. Even spending $20 here or there at the beginning was difficult for us.

(See also: How to Save Money When Renting a Car for a Large Family)

Hopefully if you’re a frugal cheapskate like me, adopting a “rule” like this will give yourself permission to spend money in the name of keeping your family sane. (Note: Since budgets are different, your own “$20 threshold” might be a different number, but the principle remains the same.)

I’ll share an example of how this rule has helped our family, and one time when I didn’t follow my own advice and caused craziness (because reading about other people going crazy is much more fun than doing it yourself).

Should Have Followed My Own Advice in Dubai

Let’s start with a story from a few years ago when I didn’t follow this rule. My wife and I took a first class flight around the world (using American Airlines miles to fly JAL first class Chicago to Narita and then Alaska miles to fly Emirates First Class Singapore – Dubai – New York before the devaluation). We took advantage of the fact that you can get a free stopover, even on a one-way, when using Alaska miles in order to spend a few days in Dubai.

We checked into our hotel and then took a boat ride across Dubai Creek to spend some time exploring Old Dubai. It was getting to be dinner time, but I was so obsessed with finding a “good deal” on food that we literally wandered around for 30 to 45 minutes trying to find somewhere to eat before we ended up stopping back at … the first place we had seen.

My wife was a trooper about it (she’s used to me!) but I’m sure inside she was giving me a serious eye-roll.

Using the $20 Rule in Orlando

Last month, our family went to The Wizarding World of Harry Potter in Universal Orlando as a Christmas present. Nearly everyone in my family is a huge fan of the Harry Potter series, and I knew that Ollivander’s Wand Experience was going to be a huge draw.

(Photo by Summer Hull / The Points Guy)

With 10 of us in our party (the eight of us plus my dad and stepmom), I knew that we were really stacking the deck in terms of our odds of one of us being “chosen” to be featured in the wand selection show. Sure enough, my 12-year-old daughter was picked out of the crowd.

After the wand selection was over (and it really is a great show), the wand maker “gave” her the wand. And, of course, they don’t truly give you the wand … you still have to pay for it! As we waited in the cashier line, I mentally remarked on the genius marketing idea going on here. Because I mean who can possibly say no to a face like this?

So as we’re waiting in line, with no idea of how much this wand would cost, I started thinking to myself, “What is the maximum amount I’d pay for this? $100? $150? If it cost $200, would I still buy it?” I decided that I probably would, but thankfully it was “only” $52 plus tax.

While it was more than double the $20 threshold, mentally budgeting for this expense before we got to the park made me feel a lot better inside. (Same goes for the $60 I dropped on butterbeer for the whole family.)

A "butter beer" challenge well worth the cost (Summer Hull / The Points Guy)
A “butterbeer” challenge well worth the cost (Summer Hull / The Points Guy)

Remember, to make these sort of splurges even easier on the wallet, you could charge them to your theme park hotel room, then pay off that bulk charge with fixed-value points that work on travel (think Barclaycard Arrival Plus World Elite Mastercard or Discover it® Miles). The $20 trick doesn’t have to mean you are actually spending cash.

How Could the $20 Rule Help Your Family?

During a trip, we never know where the sources of strife may come from but here are a few scenarios in which the $20 rule may help:

Spring for a Cab or Uber: The kiddos are fading fast during a daylong exploration of a new city. Instead of making the gang walk back to the hotel or take a crowded subway, pull out that $20 and take a cab or Uber instead.

Buy the Better Tickets: Your family has their hearts set on seeing a musical but the best seats each cost a few dollars more than you were hoping to spend. If this event is one of the “signature” activities during your trip, go ahead and spend the extra cash for seats with better sight lines of the stage.

Spend a Bit More for a Sit-Down Meal: You’re at a theme park, midsummer, and temperatures are soaring. Everyone is getting hot, tired, cranky and hungry. Instead of settling on hot dogs from a stand and eating on the go, consider a fast-casual dining options where you all can sit comfortably in an air-conditioned dining room and take a few minutes out of the day to recharge while someone brings you food and drink refills.

Bottom Line

While you may not be quite as much of a penny-pincher as me, I hope that this “$20 rule” will help keep things a bit calmer for your next family trip.

If you’re looking for additional tips on how to de-stress your family vacation, check out how we use vacation schedules to let even little kids know what to expect on vacation.

What’s your best tip for keeping family vacations stress-free? Mention it in the comments.

Featured image by Bounce / Getty Images

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