An Ass-Backwards Approach to Road Trip Planning

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Written By Colin Graves

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It’s mid-April, and planning for the 3rd Annual ‘Super Frugal Road Trip’ has begun in earnest.

In actuality, it’s closer to our family’s 15th road trip of a frugal nature, but they received a fancy title when I started blogging about them two summers ago.


In our home, road trip planning usually follows a similar pattern, and when you’ve done it as many times as we have, you have the process down to a science.

While I’m all for adventure and spontaneity when we hit the open road, it’s the detailed advanced planning that enables us to pull off 5000 mile journeys with our three kids with relative ease, not to mention on less than $1000.


This year, to borrow a term once used by my dearly departed grandmother, I took an ‘ass-backwards’ approach.  Unlike my beloved Gran however, I’m referring to road trip planning, not the order in which certain offspring once decided to approach procreation and matrimony.  Bless her soul.

Normally, the process begins something like this:

  1. Select the preferred dates for our trip.
  2. Coordinate said dates with any family/friends we plan to visit along the way.
  3. Find a house sitter to care for our two dogs.  This is VERY important, and our dates need to work for them as well.

…and on it goes from there.


So, did I follow my simple 3 step process this year?  Nope.

This year, I bought tickets to a rock concert.  In Chicago.  1000 miles from home.

Before finalizing my vacation dates at work.  Before coordinating with family we plan to visit, and definitely before checking to see that we had a house sitter available.

It all started when my son texted me to let me know that one of our favourite bands was playing in Chicago in July.  As a side note, rightly or wrongly, I hold the fact that my kids share my taste in music as one of my greatest parenting achievements.

In a moment of impulse (I’m not immune), I went online and bought tickets for my son and me, and my youngest daughter.  My wife and other daughter aren’t as interested, and will be more than happy lounging by the pool back at the hotel.

I don’t normally recommend constructing a two-week vacation around a moment of impulse, but sometimes you have to shake things up!

It does however, throw into question the frugal aspect of our road trip.

Each of the past two years, we’ve managed to pull off 16-day, 5000-mile road trip vacations for our family of five for less than $750!  If you’re wondering how in the world we made it happen, you can read more about it here and here.

Doing it for a third straight year will be more of a challenge.

WORKING FROM BEHIND (you don’t have to say it, I know…)

For starters, I’ve already committed $225 to the aforementioned concert.  Because of this ass-backwards approach to road trip planning, it could drive up our expenses in other areas as well, namely:


It looks like we’ll spend 1-2 extra nights in hotels at the beginning of our journey.  Thankfully, I’ve already managed to reserve a Hyatt in the Chicago area for $89/night!  Complete with a pool, continental breakfast, and a kitchenette in our suite where we can easily prep a few of our meals.

In case you’re interested, here’s my secret to saving so much money on hotels:

I book almost all of my hotels on this site, and highly recommend it!  If you have an upcoming trip planned, it’s worth your time to create an account, and check out the incredible savings.

If you’re interested, you can use my exclusive link.  There isn’t the space here to detail everything that makes so great, (one of these days I’ll write an in-depth review), but you will save a ton of money booking your hotel stays through them, period.  

Meal Planning

Eating out is something we always look forward to when we’re travelling.  But with a family of five it would get real expensive, real quick if we ate every meal in a restaurant.  Instead, we mix a few nice restaurant meals in with more frugal food options.

For example, we always stay at hotels that offer continental breakfasts (preferably hot), and pack sandwiches, fruit and healthy snacks in a plug-in cooler for our long driving days.  This also helps us reach our destination that much faster.

This year, spending extra time on the road may require more restaurant stops, so we’ll need to find some creative ways to stay within budget.

House/Dog Sitting

When we travel for any length of time, we usually have a family friend stay in our home to care for our two dogs while we’re gone.  It’s a great arrangement all around.

The young guy who usually helps out loves having a place of his own for a couple of weeks (he lives at home with his parents), and we feel good knowing our dogs are being well cared for.  We fill the fridge with food for him, and buy him a gift card when we get back.

This year, I didn’t check his availability in advance.  I just booked a concert.  Remember?  Ass-backwards.  Anyways, as it turns out he’s travelling at the same time we are.  Because of this, we’re now scrambling to find another house sitter.

If we aren’t successful, we may need to leave our dogs at a kennel, which would not only be expensive, but something we prefer not to do.  The kennel is actually really nice, but it’s a long time to to leave them there.

There you have it.  Three potential budgeting complications due to my ass-backwards approach to road trip planning.  Stay tuned to see how things turn out!

PS.  As for the concert details…. Foster The People & Paramore, outdoors, downtown Chicago in July.   It doesn’t get much better! ?

Question:  What are your vacation/stay-cation plans for Summer 2018?  I’d love to hear about them.



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8 thoughts on “An Ass-Backwards Approach to Road Trip Planning”

  1. I’ve loved seeing how you guys structure your trips and keep them frugal – it definitely gives us something to strive for!

    Hope we are able to meet up when you drive through – we’ve got a bit of a change in our travel plans so we should almost certainly be around!

    • Thanks Chris! Definitely hoping we can connect on our way through! I’ll send you a DM and let you know how things are looking date-wise at this point. Looking forward to hearing all about your travel plans as well! 🙂

  2. Oh enjoy your trip MMM. We have a dog and making sure we have someone to care for her whenever we go away is always such a stress. We too would prefer not to leave her in a kennel. Luckily my babysitter will usually take her for me when we are away for a reasonable sum. Finding people in your life who can play these roles is so important for being able to enjoy time with your family and get away. It will work out one way or another, I am sure!! Your trip was epic last year, can’t wait to hear about your next one!

    • Hi Linda, Sounds like you’ve got a really great babysitter! We love our dogs, but they can make travel planning a challenge. We used to bring our small one along with us, but doing so really limits our activities when we’re on the road. Yes, can’t wait for our trip, feeling the need to get away! 🙂

    • Hey Troy! That’s a good thought. I find that if I don’t plan at least a good portion of the trip, I end up not making the most of the time. That said, I think if I was travelling solo I would do less planning, take things as they come. : )

  3. I adore your road trips. This sounds something I want to adapt, just have to wait a couple of years for the girls to become a little bit older and become able to process and enjoy the awesome places we could visit. Our “little” Europe is not like your giant US but still has some interesting views.
    This year we plan to visit Greece in the late summer. We are practicing booking early for season end dates which cuts vacation prices into half at least.
    Keep us informed and thanks for sharing!

    • Thanks HCF! I’ve never been to Europe, would absolutely love to go…someday. Greece sounds amazing, by the way. I’d love to hear more about the plans for your trip, if you’re ever so inspired to write a post about it! As for us, our plans are coming together. It looks like we’ve found a house sitter for our dogs. That’s one big hurdle out of the way!


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