Updated on 04.05.12

How We Plan for a Summer Vacation

Trent Hamm

A few days ago, I mentioned that my family and I are going on a summer vacation to South Dakota and eastern Wyoming, where we intend to see Badlands National Park, Black Hills National Forest, Devil’s Tower, Mount Rushmore, and several other things in the area.

Several people wrote to me after that post asking for details on our trip planning. Most of them were from people who were also planning trips to the South Dakota area in the next year or two, but at least a few were looking for some strong general tactics for frugal family vacation planning.

We’ve become fairly adept at planning out affordable and memorable family vacations over the years, even with young children. Just in our oldest son’s lifetime, we’ve taken long trips to the Chicagoland area, Lake Superior, Texas, western Washington state (this was the only non-road trip), and now to South Dakota and Wyoming. Each of these trips has been affordable and enjoyable for everyone involved.

I’m usually the one in charge of planning our family vacations. Here’s the process I use for planning them.

Pick a location, not a destination
If you center your vacation around a specific destination (say, Disneyworld), that becomes the focus of the trip. Other opportunities in and around that area become secondary to the destination, and the destination is often an expensive one.

Whenever we plan a trip, we try to make the location of the trip as general as possible. For example, we could easily say that this trip was to the Black Hills National Forest, but instead we’re thinking of it as a trip to South Dakota and eastern Wyoming. That way, the trip’s focus isn’t just on the Black Hills.

Look for everything of interest within that location
One great way to do this is to order a state or regional visitor’s guide (or look one up online). Almost every state has a department of tourism that produces a wonderful traveler’s guide for their state.

For example, South Dakota has a great website listing things worth seeing and doing within the state.

Over a period of a few weeks, we looked through these guides and marked everything of interest to us, which was quite a lot. I made special note of things that seemed interesting that were also free (or very low cost), as these activities would provide the backbone of our trip.

Use Google Maps to plan the route
After a while, I started marking locations of interest within Google Maps. This helped me to eliminate locations that were outliers. For example, there was some interest in visiting Wounded Knee, but there was nothing else marked within two or three hours of driving of that location, so we eliminated it from consideration.

Eventually, we recognized that most of the things we wanted to see (at least, ones that weren’t outliers) were fairly close to a single driving path, so we set that as our driving path.

Be loose with the trip planning
For each of the “pins” marked on Google Maps, I will be printing off an address and a page of information describing what it is and why it’s interesting. We’ll assemble these (along with the maps) in a “trip binder,” which we’ll take along on the trip.

To this point, we haven’t scheduled anything with a specific time or date. There may be things that require a specific time or date when you travel, but you’re better off minimizing those and allow your schedule to be flexible, because there will always be interesting impromptu things to see on an open-ended trip.

Look at a wide variety of housing
Housing on vacation doesn’t have to simply mean booking a hotel room. If you’re driving in the area, camping is a possibility, too. If you have a large group, a cabin in the area might be less expensive, considering you can make some of your meals there.

Rather than just hitting something like hotels.com when looking for housing, we use things like TripAdvisor and look at options like camping, cabins, rental homes, and other options.

Which one is the right choice? It depends on your group composition, really. For some groups, camping would be the best option (this is certainly true if it’s just my wife, my children, and myself). For larger groups, a cabin might be the best option as it might reduce the cost per person to a level lower than a hotel. There may also be people with special needs in the group that lean you toward one option or another.

The key is to not limit yourself to just hotels. There are many less expensive housing options if you expand your horizons, particularly when you consider places that enable you to make most of your own food instead of constantly eating at restaurants, which can really add up.

Use the “peak-end” rule
On our trips, we usually let everyone select one thing that they really want to do out of the options and we make sure that we do that thing, no matter what it is.

For example, I really want to see the Crazy Horse Monument, while my wife is very excited about going to Devil’s Tower. Our oldest son wants to hike in the Black Hills, and our daughter wants to see Mount Rushmore. All of these are things we will definitely see on the trip.

Simply put, we make sure everyone has a great “peak” experience for the trip.

Similarly, we try to figure out one thing that we all have a strong interest in doing. For the parents and the two older children, the one thing we all really want to see is a gold mine. (Yes, seriously. We’re kind of quirky.) We plan on doing this on the last day of the trip, providing our “end” experience.

Everything else we do is really secondary to these things, because most of our memories from the trip will come from our “peak” experience and our “end” experience, and as long as we’re all happy with those, the rest of the trip can be filled with whatever may come. That’s why we have a trip binder with many free options to fill our days.

The result of this planning is a family vacation we’ll all enjoy that’s not loaded down with expensive destinations. It’s worked wonderfully for our last several family vacations, and we don’t see it changing for this one.

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  1. kc says:

    Trent, I realize you sold the site, but I find it curious that you haven’t commented at all on the stringent comment moderation that’s in place and how it’s impacting the site.

  2. Arianna says:

    I highly recommend Custer State Park too — SO MUCH wildlife, in a nice, driveable loop that takes less than 2 hours, and it’s less than an hour from Mount Rushmore. Also not too crowded. My mom and I did these things on a road trip almost 10 years ago and I still remember gaping in awe at the giant buffalo that was taller than my Honda — and right outside the car window!

  3. mary w says:

    Nice post. Decently written. Good info. This is the type of post that brought me to TSD originally.

  4. Stacey says:

    Chamberlain rest stop is a must if u r traveling the interstate. There is also a native American museum at st joes Indian school there worth seeing.

  5. Troy says:


    That would require acknowledgement that the comments are more valuable than the posts. With the comments, this site is “entertaining.” Without, it’s nothing

  6. Katie says:

    I’m genuinely curious whether cultivating an active comments section is necessary to the financial success of the site. Maybe not?

  7. Katie says:

    Though, that is the first comment I’ve had go through in a long time, so maybe Cut Media is tweaking things to work a little better.

  8. Kevin says:

    Most people come to this site for the comments – you would think they would want to keep them working.

  9. jim says:

    Frankly I see no reason to see why the comments would make this site any money. Its mostly just a handful of people arguing with each other and bashing Trent. (yes that includes me) I mean seriously…

  10. Johanna says:

    Most people who *comment* are here for the comments.

  11. Jackson says:

    Many of the comments are more interesting, more knowledgable and better written than Trent’s posts.

  12. Katie says:

    Whoops, moderation. Posting in bits: “Johanna: Yes, exactly!”

  13. Katie says:

    Maybe commenters and comment readers really are a small portion of the page views (income) here,

  14. Katie says:

    …so it’s not important at all to cater to them by trying to make comment moderation work well, or even to try to cultivate a less crabby comment section by banning people who are consistently negative. : )

  15. Katie says:

    I like the peak-end idea, though.

  16. Joan says:

    #6,7,12,13,14,15 Katie What great interesting comments you take the time to write.

  17. Johanna says:

    But it’s scary that people come here for Trent’s wisdom.

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