I just survived 15 hours in the car with my eight and five year old boys without losing my mind. Before the trip I was worried about how to keep them entertained and not crabby for two days on the road. Thankfully this idea worked like a charm.
Of course, we heard the age old question, “Are we there yet?” a gazillion times. But instead of an undertone of dread, the boys were asking with excitement the whole way.
My survival plan was a mashup of two gift ideas from my friend Lauren’s book. She just released the new edition of Thinking Outside the Gift Box*. I knew I wanted to bring it to read on the trip, but I’m so glad I flipped through it before we left.
What I love about Lauren’s book is the new ideas it sparks every time you read through it. Since I had road trip on the brain I instantly latched on to gift ideas that would keep the boys happy on a long car ride.
I knew gift idea #33 – Road Trip Survival Kit was a must. Then when I came across gift idea #43 – Gift A Day, the perfect mashup was born. The Gift a Day idea was the perfect way to to tweak the road trip survival kit to last the whole way from Minnesota to Texas.
Instead of a gift a day, I made it a gift per milestone. I tied each gift to a point on the map along our route. Every time we crossed a state border or hit a major city, the boys were allowed to open the designated gift.
I got most of the prizes in the Target dollar spot. I only splurged on the headphones and water bottles that would last beyond the car ride. The prizes don’t have to be fancy…when trapped in a car for two days, they boys were equally excited by a blank notebook and pencil as a pack of jelly beans.
Their road trip prizes included:
- Start: Headphones and water bottles
- Milestone 1 – Iowa Border: Chocolate Bar (This early surprise treat helped build excitement for future prizes.)
- Milestone 2 – Des Moines: Blank notebook and two mechanical pencils
- Milestone 3 – Missouri Border: National Geographic book
- Milestone 4 – Leaving Kansas City on Day 2: Star Wars stickers
- Milestone 5 – Oklahoma Border: Coloring book and crayons
- Milestone 6 – Oklahoma City: Star Wars Jelly Belly (These fended off any last leg crankiness. Plus they entertained the boys as they slowly worked through trying and guessing each flavor of jelly bean.)
All the prizes were individually wrapped, numbered, and stashed in each boys’ backpack. Every time we reached a milestone on the map, they opened the corresponding package. The numbers simultaneously served as a trip countdown, because they knew how many packages there were.
Whenever they asked, “Are we there yet?”, we were always less than two hours away from saying, “Yes and you can open your next prize.” They always had something to look forward to. It even seemed like the second day went better than the first. And once a prize was opened they had an activity or treat to keep them happy until the next milestone.
It worked so well, we’ll be hitting the dollar spot to wrap up some more prizes for the trip home.
As for me, I passed the time with the new edition of Thinking Outside the Gift Box* loaded on my iPhone, an unhealthy amount of Justin’s Peanut Butter Cups, and a notebook in my lap to plan out this year’s Christmas presents. I’m looking forward to some more gift idea mashups, especially for those hard to shop for people on my list.

Get your copy of Thinking Outside the Gift Box here* and be the one that gives the most thoughtful gifts.
*Disclosure: I am an affiliate for Thinking Outside the Gift Box and this post contains affiliate links. If you purchase Lauren’s book after following a link in this post, I will receive a small commission at no cost to you. I only share and recommend products I’ve used myself and love.
Jackie, this mash-up is AMAZING. I love that the gifts served not only as entertainment, but as a gauge of time, and even a little geography lesson! SO blown away by your creativity here. And thanks for the incredible shout-out for my book! So very glad that you’re able to take the ideas on those pages and make them your own. That’s what it’s all about! Off to share….
Flipping brilliant Jackie! We’ve done many road trips and none with anything as smart as this. Looking forward to doing this next summer. :)
Angela, It worked so well my boys were asking days ahead of the return trip if I had prizes ready and they had memorized the order of the borders or cities where they got prizes :)