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Want to Plan a Road Trip? Here’s 5 Steps to Get You Started!

05/21/2014 · 2 comments

Recently a Great Family Road Trips reader (and in-real-life friend) Shari asked:

“We are planning a short road trip from CT to Chicago at the end of June. We are giving ourselves 1 week. Where is a good place to start for finding family friendly hotels, activities, food, rest stops, etc.?”

How to Plan a Road Trip

YES! A road-trip in the making…. I love the planning stage- so full of possibility and adventure!  When I sit down to start working out the details- here’s how I like to plan a road trip:

Step 1: Map It!

Map It

How long is going to take to get to the final destination? All in one day or a stop (or more) in between? Pick your route and your rough itinerary. In the case of the CT-Chicago road trip- you are looking at 13+hours driving time, with stops and possible traffic you are looking at more like 15-16 hours. That’s quite a long haul.

Break it Up

So perhaps breaking it up with a stop in Cleveland on the way out (8 hrs to Cleveland on Day 1, 5 1/2 to Chicago on Day 2), and then maybe a day in Sandusky, Ohio on the way back to play at Cedar Point amusement park (4 3/4 hrs to Sandusky, 9 hrs to get the rest of the way home) would be a better way to break up your trip and have more fun along the way!

Step 2: Google It “with kids”!

Google It

When I am traveling to a new place- one of the first things I do is to Google the name of the destination followed by “with kids”, as in: “Chicago with Kids”. In the first 2-3 pages you will get a nice collection of articles written by travel sites or newspapers, bloggers who either live there or have taken the kids there on vacation, as well as tourism bureaus who offer up great lists of things for families to do for their location.

Take some time to scan through some of the articles and make a list of attractions that would be appealing to your kids. Then start plotting them into an itinerary:


Step 3: Think of One or Two Things That Would Make It Awesome for the Kids!

You might not be thinking about mini-golf while planning a trip through the midwest- but if it is on your kids’ summer bucket list- it would be great to find a mini golf place along the way and make it one of your rest stops. Again- here I would hit up Google for ideas… “mini golf off of I-80 in PA” turned up Fun Central right off of I-80 in Clearview PA (a town that I have driven past more than a dozen times in the past few years… and I never knew about this place!). It’s adding in little things like this that will go a long way into making this a vacation your kids will love!

Step 4: Check Out Favorite Web Sites for Hotel and Dining Recommendations

Mini Time

Now that you have a rough itinerary of where you want to go and things you’d like to do, it’s time to find the right place to stay and some great places to eat along the way! Of course some day I hope to be that resource for you! But until I have covered enough territory- I suggest you check out some of my favorite family travel sites:

Step 5: Next Exit

GPS vs Maps- Next Exit.jpg

I have written about this book before- but I truly think that Next Exit is one of the best items to have along with you in the car on a road trip. You simply look up the road you are traveling on, and you can see what fast food places, restaurants, or even hotels are up ahead!

So fellow road-trippers- this is how I plan a road trip! What tips do you have to add to this list?

{ 2 comments… read them below or add one }

Shari May 21, 2014 at 9:47 am

Great post!! Thank you for breaking it down into manageable pieces. The planning stage felt a little overwhelming:)


Manish Chaurasia December 6, 2017 at 12:55 am

Thanks for writing such an interesting article on how to plan a road trip in 5 steps.This article will surely help me in planning my future road trip .


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