How to Plan a Road Trip Itinerary: Step by Step

When it comes to roadtrips with kids, the fine line between awesome and awful is in the planning. Anyone can plot a point between A and B, gas up and go, but with great roadtrips, it’s all about the journey. The destination is just the happy finality that points you in the right direction. What you do with the miles in between makes or breaks the trip.

Step One: Choose a beginning and end point.

Most often, roadtrips start and end at home, so half of the work in plotting the bare bones route is done. Your destination will depend upon your goals. Are you headed to see relatives or to visit a city you’ve never explored before? Pick an destination, even if it’s a general one, for the destination. Whether you are planning a lengthy road trip or a multi stop trip, plot out your initial route using an app like Mapquest. It helps to be able to see what area you will be traversing on your planned route and how many miles you will travel.

That’s when the fun begins!

Step Two: Set your dates

Once you know where you are going, you have to consider how long you can take to get there. Set your date points in a spreadsheet or a word document. It doesn’t have to be complicated, but you need a way to visually see how far you have to go to meet your calendar deadlines. I like to plot my road trips with a spreadsheet that shows the date, the destination for the day, the miles/hours I will travel that day etc… As I add more details to my planning, I can add a column for lodging confirmation and notes for stops and activities along with way.

At this stage of the game, I just add a column with a date for each day that will be traveling and leave the other details blank.

Step Three: Take a good look at the miles and consider your needs.

Kids- and the parents who drive them-have a road trip time limit that exponentially decreases based on the age of the child. Generally speaking, the younger the child, the shorter the time you can expect to spend in the car a day. When my boys were little, six hours was the absolutely outer limit that we could handle in the car. Over the years, they have built up enough resistance that we can do 10 hours easily, and can even push a 12-14 hour day when necessary.

It’s hard to know how your kids will do in the car until you give it a go, so start with some shorter trips and work up to the longer ones. Find the outer limit that your kids can tolerate in transit and try to stick with that each day.

*Important note: when figuring the travel time by car with kids, be sure to add in the amount of time you will spend stopping frequently. I usually add 15 minutes of travel time to every 2.5 hours of road time for potty breaks and wiggle breaks. Also don’t forget to add the time to stop for meals and a few good stretch breaks for the driver.  Be sure to know your total travel time, not just the miles on the road.

Once you know how far you can go in a day, that will help you plan the stops along the way.

Step Four: Decide where you need to stop for the night.

Knowing how long you can stand to be in the car will help make the next points on your route as your places to sleep for the night.  Geography and budget can both play a part in deciding where you lay your head.  If there is a major city along your route that matches the amount of time you want to be in the car, that is the best place to start your search for overnight accommodations.  Once I have pinpointed the major cities that fit my timeline, I like to do a little hotel search in that area, but I don’t just look at hotels in that city, but the smaller cities on the outskirts. Often there can be a big savings by stopping a few miles early or going a few miles past.

I also spend some time investigating whether my overnight city has a chance of being a mini-stopover city. The best way to do this is to do a simple search for “Things to Do in XYZ” and see what comes up. If you see something that appeals to you, it might be worth taking a day or two off the road and exploring in this area for a while before heading out.  Be sure to check the surrounding areas, as well to see if they hold any promise for a hidden gem that’s worth a stop.

*Important note about lodging in stopover cities: If I am just looking for a place to stay for the night, I look for a barebones lodging that is close to the major highway. Included breakfast is the one option that I really like to have, but other amenities are not important. I will very rarely spring for a suite or double rooms if I am just crashing there for the night. We always road trip with a blow-up mattress to have enough beds for everyone in these scenarios.  If I find that it is a city where I want to stay and explore for a few days, I am choosier about the amenities that I need and a space that allows our family to spread out.  

Step Five: Examine your route for worthwhile overnight stops

Once you know where you have to stop (she can’t take much more Captain!), then you need to decide if there are places where you could stop. Some of the best places are the smaller cities and towns between here and there. If it is big enough to be listed on the map, do a quick search and see if there is a worthwhile museum or unique attraction that warrants an extra stop. If you find several things to interest and occupy, it might be worth an overnight stop. Overnight stops with a fun itinerary make the time on the road much more bearable.

Step Six: Plan for extra fun stops along the way

Most roadtrippers get as far as step five and stop, missing the cherry on the sundae part of roadtripping. The weird and wacky detours to roadside attractions, or hole in the wall diners that serve pancakes the size of your head are what make the miles on the road worth driving.

Once you have your destinations in place and know where you are stopping for the night, do a little digging and see what fun surprises you can add along the way. For kids, these are often the most memorable parts and they certainly make the miles more bearable.

To find these hidden gems isn’t so hard, especially using the great collection of apps that are designed to help roadtrippers find the good stuff.  Roadtrippers and On the Way  are two great web-based route planner to help add all the fun details. Roadside America is another website that holds the key to the truly kitschy side of the road attractions. Personally, I never feel like I’ve completed my plans unless there is at least one oversized ball of string or giant soup can on the route. 

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