Get Your Kicks… and Then Some

Part 1: Planning a cross country family trip

We’re a homeschooling family – Mom, Dad and 4 kids – and we love to learn on the go. We’ve explored Washington, D.C., Williamsburg, VA, and several sites in our historically rich native South Carolina. Our kids range in age from 5-14 years old and this year seemed like the perfect time to go on a BIG trip. Having only planned short trips and single destination trips, I quickly realized I had to have a plan for a cross country, multi-stop, road trip. I’m sharing how we chose our timing, route, budget and more!


As a homeschooling family, we love the flexibility it allows us when it comes to traveling. We typically vacation during the traditional school year so we can find good rates and beat the crowds. However, when my husband took a job as an adjunct professor, that threw a whole kink in our plan to travel cross country in the fall. Being the super ever-flexible wife that I am (insert mild sarcastic tone here), I rolled with the punches. Grabbing the university calendar, I figured out we can do the entire trip we wanted between the time of his last class at the university and Memorial Day-ish. So, not too shabby.

Route Planning

Once that was established, then came the route planning. We’re an East Coast family and can pretty much visit most places east of the Mississippi in a long weekend/week. So, we’re concentrating our planning on places we’re not likely to re-visit in the near future. Somewhat jokingly, my husband suggested we drive Route 66. I blew that off at first, but once I started looking at a map, I began to come around. We also knew we wanted to try to fit Mt. Rushmore into the trip somehow, which was the one big kink in the plan. So, we adapted the plan. What we came up with is a plan to drive and be gone 17 nights from our home…the longest vacation we’ve ever taken as a family. The only close rival is a previous Disney Trip and so much of that trip plans itself for us. I knew we’d need a serious plan for this trip.


Another intimidating task for me, after deciding where all we wanted to go, was setting a budget. We live pretty frugally throughout the year so we can splurge a little on memory making. To set our budget, I broke down the expenses in the following categories: Gas, Vehicle Rental, Food, Accommodations, and Experiences/Attractions. I’m almost certain that I’ll realize I’ve left out a glaringly obvious one about a day into our trip! For that reason, I overestimated in every area. Figuring the budget took some calculating and Googling.


I researched average fuel prices plus miles per gallon of the rental. Then I took the estimated miles traveled and did a little nerdy math. When I came up with a number, I inflated it a little to account for any crazy detours or rise in gas prices.

Vehicle Rental

We chose to rent a 15 passenger van because it has lots of room to switch around seats during our MANY hours on the road. It seemed a much better option than “He’s touching me!” for 17 days! We rented through Enterprise. Interestingly enough, by chosing an Enterprise location a little farther away, I saved almost $600 on the same vehicle available at the closer location.


I always plan big for food, too. Because we’re visiting so many different parts of the country, we like to taste our destinations, too. We’ll likely do some snacks in the car and a few days where we eat on the cheap in our home/room, but we’re going to check out some good eats along our path.


For accommodations, I just searched for rooms at decent hotels on booking sites and made that my goal price. With only 1 exception, I was able to find places within my budget.


This line item was simply a shot in the dark. We have a fourth grader this year, so our whole family gets into to National Parks for free. That’s pretty cool! We’ll certainly take advantage of that where we can.

Getting Organized and Finding Assistance

We’re not super high tech people. We like to use technology to enhance our experiences, but we always want to enjoy our physical environment as much as possible. I work on a computer far more than I work on my phone, but I wanted to find a tool helpful in planning our trip and figuring out stops. After some searching, I found Roadtrippers. Roadtrippers allows you to map and save a trip and plug in different stops along the way. It shows a mileage tally – both between stops and for the total trip – to help figure out how to balance covering lots of ground as well as enjoying stops along the way. I’m sure it has many features I haven’t explored yet, but so far, I’m loving the app. It also plugs in new destinations where they make the most sense along your route, but allows you to change it if you so desire. We also grabbed a road atlas (affiliate link) to have a hard copy of maps in case we’re without service or just need to unplug a little.

Booking Accommodations

By looking at our route, the stops and the number of hours driving between cities, we established how many nights we’d stay in each place. Any cities that had us staying one night, I booked hotel rooms through or directly through the hotels – depending on which had the better rates. The cities that had us staying 2 or more nights, I booked a house on Airbnb or VRBO. Laundry facilities were a factor because we’ll only pack for about 4 or 5 days and do laundry at our stops. There were a couple of cities (Salt Lake City and Nashville) that were difficult to find accommodations within our budget. I accepted the challenge and thought outside of the box a little. In the Salt Lake City area, we booked a condo at a ski resort. Since it will be the off season, our rate for a 3 bedroom condo was a little over $100 a night. In Nashville,I found a state park with really nice furnished cabins. Since we’ll be there during the week, before schools let out for summer break, I got a great rate there as well.

Figuring Out What to Do

I had no idea how much of an inner nerd I actually have until I started planning this trip. A novel series I was reading led me to this book (affiliate link) which contains TONS of tips and tourist attractions along Route 66. It’s intended more for folks who are serious about traveling the Route, but it has some great information.

When we DO Disney, we go, go, go until we can’t go anymore. On this trip, we want a balance of activity and leisurely exploration. I’ve found myself fighting the temptation to plan to do ALL THE THINGS in each city. Trip Advisor has been a great resource for figuring out some of the things we don’t want to miss. At this point in our planning, my motivation is beginning to wane and I’m considering just winging it, but I know that will likely be a terrible idea in the long run. My procrastination will kick in and I’ll spend a few late nights adding to the list.

Waiting Well

Now that the hard parts are done, we just wait. Since we started early in our planning, it’s easy to almost forget about the trip. We’ve got a few life stresses happening right now with trying to build a house and having to move from our rental before we build. It’s thrown us for a bit of a loop. We needed a boost! I love a good countdown to help build excitement for a trip, so I threw this one together real quickly using a puzzle and chalk board from the dollar store. It’s kept in a prominent place in our home and the kids are loving marking off the days. In our waiting, I’m also mentally packing bags. Stay tuned for more tips, tricks, struggles and/or surprises!

Any good tips for traveling cross country with your family? Comment below!!


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