Learn to Plan the Ultimate Road Trip

Road trips can be the most memorable things you ever do with your family and also one of the most overwhelming. Traveling together is one of the best ways to solidify family culture – take off on the road for several weeks with no one but each other for company. Forced togetherness. Not only do you get to see great parts of the country, you work through struggles and come out stronger in the long run. Isn’t there a quote about family who camps together stays together?

Despite how much I enjoy planning road trips – seriously, a compulsion – it seems that not everyone feels the same way. Or has the time. Or energy. Or even brain width to manage it.

While planning trips relaxes and excites me, I’ve also realized that this shouldn’t be a drain on the time at home you have with your busy family. And if Mom and Dad are already annoyed before you ever get on the road, it’s only going to go downhill from there, and no one wants that.

“I don’t even know where to start!”

Where do you want to go? Back up. Way up.

How much can you spend? Nope. Back up further. There are always more expensive or cheaper ways to go. Let’s cross that bridge later.

While it’s fun to start daydreaming and looking at exotic locations and your bucket list, just stop for now.

How long can you be away from work or school? 

Growing up, I always wondered why anyone would ever fly somewhere. You miss out on so many sights along the way. But then, the adult-world hit and I realized that not everyone has three months off in the summer like we had with my teacher parents. That just means that maybe we just need to think outside the box!

• Does everyone in the family have the same time constraints?
• Could some of you drive, and Dad flies to meet you later?
• Are there special events or appointments that have to be worked around? Can you change them?
• Do you have friends or family you need to visit (or avoid) along the way?

What type of trip do we want?

Notice I said “we”. Remember, this is a FAMILY adventure not Mom’s adventure that everyone else gets to go on. 

• What is your travel goal? 
• Are you out for adventure and backpacking through the mountains while white-water rafting through a canyon?
• Has life been crazy and you really just need to veg on the beach?
• Are you history nerds who want to soak up all the American history on the way?
• Do you want to see everything you can do because this is your one chance?
• Or… Are you more of a rest on vacation because it’s the only time you get?

What is best for the family needs?

As a homeschooling family, I want to get out and go and see everywhere as part of our learning lifestyle. However, Dad doesn’t get to go places as often as we do because of work and wants to relax during his time off. Maybe both parents yearn for adventure, but the littles still need their afternoon nap and have never traveled longer than two hours to Grandma’s at Thanksgiving – a drive everyone remembers because they screamed the whole way.

• What distance can you drive in one day?
• How often do you need to stop for breaks?
• What level of busy do you want for your vacation days?
• Do you have any special food or medical requirements?
• Do you need room to run around like a rental house backyard or is a small hotel room okay?
• Who needs a nap? — Ignored sleep can sure mess up a trip!
• Did you over-plan before and regret it? Did you sit around the hotel bored too much?
• What did you do for your last vacation and how did that go?
• How long can the kid tolerate a museum before everyone wants to run out screaming?
• What is Dad’s tolerance of Mom’s side trips to see random things? (Maybe just a personal problem? Ha! )

What is our big budget?

And does money matter for this? This part of trip planning is the time for Mom and Dad to have “the talk”. The kids just want to go to the beach. You start daydreaming this has to mean Hawaii; the kids would be happy with the one four hours away. True?

If your family is like ours, Mom lives in reality world while Dad lives in money dream world. This will be a source of contention during the trip if you don’t get it out in the open right from the beginning. Remember, travel isn’t fun in the long term if you’re going into debt to do it!

• Have you set money aside for trips? If not, do you need to hold off and do this first?
• Do you have a membership reciprocity pass to save money?
• Have you saved up plane miles or hotel points?
• Are there bigger long-term travel plans that need to be saved for as well?
• Can you dream the big trip for a couple of years and focus on the do-able now?

What is our budget for extras?

If our recent Key West family trip taught me anything, it’s that some places will just require extra money on top of the cost of getting and staying there. If you’re going to the snorkel capital but don’t have money for a snorkel trip, maybe this isn’t the year. If you’re headed to a big city to see the sights but are too cheap to cough up at least an extra $100 per day for special tours or entrance fees or taxi rides, maybe this isn’t the year.

Don’t forget to take into account the extra purchases you might need like snorkel gear, travel stroller, hiking boots… The special zoom lens for your camera to take pictures of the humpback whales. You get it. See the all-encompassing picture and not only the big picture.

Where should we go?

Kids and parents alike get excited about vacationing if they know what’s in it for them. Everyone needs a specific thing to excite them.

• What are some places have you studied in school?
• Where did you go as a child that you want to share with your kids?
• Where have the kids heard friends go that sounded interesting to them?
• Watch some travel shows and daydream together.
• Open a map and figure out your furthest distance and narrow it down from there.
• Pull up the National Park website and find some national parks to explore. (Remember, fourth graders get a yearly free pass to get into National Park sites!)
• Scan through this website and other family travel websites for ideas.

Now is the time to pull out the big travel planning sites and apps. My favorites are TripAdvisor, RoadTrippers, and Pinterest. I have a list of potential places saved everywhere, and I’m always looking to add more. My most used weapon is probably TripAdvisor for the mere fact that I can save places as I hear about them and later pull them up in a map. Doing this allows me to go to the area we are considering, see the little hearts scattered around, and consider which ones are close to each other.

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