The Secret of Inverse Vacation Planning

Last summer, Sarah and I took our family to Cuyahoga Valley National Park for a couple of days as part of our summer vacation looping around most of the Great Lakes.

This summer, Sarah and I are taking our family to Yellowstone National Park and Grand Tetons National Park as the centerpiece of our family vacation.

Why did we choose those places? A big part of the reason was that our two oldest children are in upper elementary school and the National Park Foundation offers a wonderful program (that I truly hope continues in the future) called the Every Kid in a Park program.

Basically, if you’re a fourth grader in America, you can visit the Every Kid in a Park website and download a free national parks pass for you and your family that lasts for a full year. This enables us to bypass the cost of entry at our national parks, which means that a summer vacation that involves or is centered around a national park now comes at a discount.

Thus, this past summer, this coming summer, and a summer or two down the road (when our youngest child reaches fourth grade) will all involve stops in or will focus on a national park or two.

A few days ago, while listening to an old podcast of Clark Howard’s radio show, he was discussing vacations and said, “Buy the deal, then figure out why you want to go there.” I realized immediately that, to an extent, we did exactly what he was talking about. We found the deal first, then planned our vacation around the deal. It’s something we do most years, actually.

Planning your vacation in that way is the exact inverse of how most people plan their vacations. Typically, vacation travel planning starts with a destination in mind, then moves onto finding deals centered around that destination.

For example, several of our summer vacations have been launched by a friend or relative inviting us to visit and stay with them for several days while we see them and enjoy their city and the area around them. I have an extremely hospitable cousin in the greater Chicagoland area, for example, and she absolutely insisted multiple times that we spend several days in the Chicago area, where she took care of almost all of our meals and our housing for us. That’s a huge bargain and it allowed us to have a much smaller vacation budget and to focus on a handful of experiences we really wanted to have (like visiting the Art Institute).

Another example: we once spent our summer vacation staying for free at a cabin that was owned by a friend of a friend who basically just let us stay there without paying a dime. When the offer came up, we planned our summer vacation around it.

We’ve flown our entire family of five to the West Coast and back for less than $600 in the past, straight from Des Moines. I’ve flown round trip to Texas and back for less than $80 in the past. Both of those were the starting points for family travel.

How do you plan for vacations like this? It’s actually pretty simple.

First, pay attention to the events in your life. We found out about the Every Kid in a Park program thanks to our oldest child’s fourth grade teacher, who told us about it early in the school year. We found out about opportunities to visit family and stay in the cabins of friends simply by being present and paying attention at family events and weddings and dinner parties.

It’s easy for things like those to slip right through the cracks. Don’t let it happen. Whenever I hear about an offer like that, I make a note of it in Evernote so I can return to that idea later on. I try to keep the idea front and center in my mind so that when vacation planning begins to happen, I recall that idea first and start there.

Whatever tool you use to remember stuff for the future, whether it’s a notebook or emails or a calendar or whatever, take advantage of it and write deals you’ll want to revisit in the future down in that storage tool. That way, you have a strong chance of seeing it when you start planning for vacations.

Another strategy I use is to start searching for huge flight discounts far in advance of any vacation days. I’ll go to SkyScanner and Kayak and simply search for all flights departing from Des Moines or Chicago (which is convenient for us thanks to the accommodating relative I mentioned above) to anywhere over a huge range of dates. Just choose dates that are anywhere within the possible span of when you could take time for a vacation and see what pops up.

Almost always, I’ll find a ludicrous deal or two, like a domestic flight to a city for way less than $100 a person or even sometimes flights to Europe for $100 to $200 a person for everyone in our family. Note that these deals are irregular, but they do show up if you search with very wide parameters. (Although we haven’t traveled internationally yet, it’s very likely that such a tool will help us with a cheap international trip in coming years.)

Between those two strategies, you should have some discounted destinations in mind for your summer vacation. Center your vacation around that enormous discount. If you can fly round trip to the UK for $150, then plan a vacation in the UK and start bargain hunting for the other things you’ll need at that location, like cheap lodging. If you have a free pass to Disney World, figure out how to make the other elements of that trip as cheap as possible.

Maybe you’ve found a huge discount on travel to a particular destination that you don’t know much about. Well, start researching that destination! What’s there that might interest you? What could you do or see there? Start learning about what’s available in a particular area and what might make for a pleasurable vacation for you in that area. Everyone’s got their own thing that they like when traveling – I personally just like to wander around cities and visit art museums – and you should center your research around that. Look at travel guides for the area and focus on things you can see for free.

The goal is to center your trip around a huge discount, then plan outwards from there. Once you’ve found a cheap flight for your family that’s within the bounds of when you can travel, or if you have a great deal on lodging thanks to a friend or another connection, or a bargain of some kind that’s well worth a side journey on your vacation or even the destination itself, start there. Figure out what’s nearby that you would enjoy. Figure out the other elements of the trip that you might need, like how you’ll get there or where you’ll stay, and bargain-hunt those elements, too.

Doing this can turn a trip that would cost thousands into a trip that costs hundreds surprisingly fast.

The key thing behind all of this is flexibility. Inverse vacation planning does not work if you’re fixated on a particular destination at all costs or you absolutely must have a particular experience on your trip. The more constraints you add to inverse vacation planning, the harder it becomes to find a good deal.

Another challenge is knowing when to bite. You’re going to see lots of good bargains when searching. The question then becomes: when does a good bargain become a great one that you should snatch up?

My best advice in terms of knowing when to strike at a travel bargain is to not bite immediately and search for a while so that you get a sense of what good bargains are – of which there are plenty – so that you have a sense of what a great bargain looks like. A flight to Europe for $300 is a good bargain, but if you wait a while, you might just find a great bargain and save another $50 or $100 or even more.

Also, don’t shy away from unexpected places. You might end up on a trip to a place that you never expected to travel to, but what you’ll find is that if you’re flexible, you’ll discover new places and new experiences and do it all at an incredible discount, whether you’re alone, just traveling with a partner or a friend, or going with an entire family.

Good luck on your inverse vacation planning!

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