The Best Family Road Trip Ever. (10 ways to truly enjoy the journey) Great tips and awesome insight from our 29 day, 4,000 mile road trip with the family. Don't even think about planning a road trip without reading this post first!

If you follow along on Instagram or Facebook, you probably already know that my family just got back from a whopping 29 day road trip. We drove more than 4,000 miles, visited 15 different states, visited lots of friends and family along the way, and made lots of fun memories that I know will cherish for years to come. After our ill-fated first attempt at a road trip back in May, we were frankly just happy to finish our journey in one piece.

Throughout our trip we had more than a few people tell us in love that they thought we were absolutely crazy, usually declaring that they could never spend that much time cramped in a car with their family. And while I must say that so much “quality” time on the road does not come without a few speed bumps, we genuinely enjoyed our time together.

As I’ve been pondering the trip and what made it so much fun, I realized that following a few important “rules” throughout the trip really helped us keep our sanity. If you are planning a road trip in the near future, or even in the distant future, here are our 10 tips for making the most of your time on the road:

Our family enjoying the best road trip ever.

1. Preparation begins at home

As far as our actual trip agenda was concerned, we couldn’t have been less prepared. We didn’t make a single hotel reservation, we didn’t let friends or family know we were coming ahead of time, and we had very few set-in-stone dates along the way. We literally took it one day at a time. We wanted much of our trip to be spontaneous, and for the most part it was.

But we did prepare in other ways. The first, and most important, way is just in our general philosophy of parenting. Taking their toys away last year was one of those pivotal moments that has forever changed us. At home they watch very little TV and instead spend most of their time coloring or reading or using their imaginations. For the most part, they don’t get bored easily and don’t constantly need to be entertained. In the car, this translated to two kids who were pretty content hanging out in the backseat. They had books to read, coloring supplies, a few figurines, and their American Girl dolls to play with, and, for the most part, that was enough.

From a work standpoint, I also spent a lot of time pre-preparing all my blog posts and finishing other assignments ahead of time so that I would have less to do on the road. I am blessed to be able to work from everywhere, but I also didn’t want to spend my entire vacation on the computer. Getting a lot done before we left helped take a lot of pressure off.

Grab a road atlas and get ready to hit the road. You'll never know what's on the horizon.

2. Take it slow

While we did have a couple of power days where we were in the car for ten hours or more, we generally tried to give ourselves lots of time and leeway to make it to our next destination. We found that keeping our daily mileage to 300 or less was usually best. In our fast-paced world where we are seemingly always late for something, it can be hard to just slow down and take it easy. It definitely took us a few days to get into the groove of not being in a hurry.

All the states we visited on our family road trip: Tennessee, Mississippi, Missouri and Florida.

3. Create family traditions

Husband and I have traveled cross-country several times, and one of our favorite road trip traditions is that we always (at least when it is possible) stop at the state lines to take a picture with the state welcome signs. We’ve now passed this tradition torch to our girls and have made it our goal to get the two of them in front of every state sign by the time they turn eighteen. Although we knocked out quite a few on this latest trip, we’ve still got a long way to go!

Trying different kinds of pie at every cafe we passed: a great family road trip tradition.

4. Always stop for pie

Small towns and out-of-the way places are the best. Our other road trip rule is that if we happen to see some small diner or cafe along the way, one of us will say, “I bet they have good pie,” and then we have to stop, just to check. Sometimes it really is great, sometimes not so much, but it is just one of those fun and silly stops that makes a road trip memorable.

Family road trips are all about visiting friends and family, while making memories that will last a lifetime.

5. Try to visit everyone you know along the way

Husband and I have both lived in many different places, and now through blogging I have been blessed to meet friends who live all over the country. (Including Crystal, Edie, and Patty pictured above.)  Thus, when we travel, we make every effort to see as many friends and family as we can. Because this trip was so minute-to-minute, that often meant calling people the day before and saying, “hey we are going to be passing through, do you mind if we stop by?” More often than not, that spur-of-the-moment meet-up was better than anything we could’ve ever tried to plan ahead of time. For the girls, meeting up with other kids along the way was definitely the highlight of the trip. They made lots of new friends and reconnected with others they hadn’t seen in a while. When all is said and done, all they really want to do is play!

Taking time the to see people is important to us because we know what it is like to be on the other end. We live in Florida, vacation capital of the world, and have often been hurt after finding out that friends or family visited the Sunshine State without bothering to let us know they were nearby. While it doesn’t always work out, at least make an attempt!

Staying with friends and family is not only a good way to re-connect, is also a great way to save money on food and hotel costs. On this particular trip, we only stayed in a hotel for 9 of the 29 nights. We are so grateful for such incredible hospitality!

No matter where you go from Tennessee to Chicago be sure to take plenty of pictures as you see the sights.

6. Stop to see the sites

This is a pretty amazing country filled with more sites than you could ever see in a lifetime. Slowing down the pace of your trip also means allowing time to stop for roadside attractions, historic sites, scenic overlooks, or famous landmarks. Never be in such a hurry that you can’t stop to explore. You never know what pit stop could end up being the highlight of your trip!

7. Play interactive games

We do have two Kindle Fire tablets that are loaded with lots of books and a few movies for the girls to use in the car. For Princess, who is a voracious reader and apparently has a stomach made of steel, a Kindle full of books was more than enough to keep her happy. Trouble, on the other hand, gets carsick very easily. Looking down at the Kindle screen for any length of time only exacerbates the problem.

Luckily we discovered the best road trip game app ever, On The Go Bingo, which we loaded onto both our iPhones and the Kindles so that we could all play at the same time. I am not even kidding when I tell you that we must have played at least a thousand rounds of that game! It was such a great way to take advantage of technology but still interact as a family, and we had so much fun playing together that even now that we are home we are constantly pointing out “bingo” sightings along the way.

Our family at a scenic overlook during our road trip.

8. Take lots of pictures

I love the quality of photos I get from my DSLR camera, but I really love the convenience of my iPhone. On this trip in particular I ended up taking most of our photos on my phone, simply because it was always close at hand. Instagram and Facebook make it super easy to share your memories and progress with friends and family back home, too. The one thing I wish I would’ve done differently is come up with our own Instagram hashtag, such as #SoukupsOntheRoad or #LWSLBestFamilyRoadTripEver. Sigh. Maybe next time!

My girls sleeping during our family road trip.

9. Rest

Travel is exhausting. Be sure to stop at rest stops while driving. On longer driving days, we would make the kids run around and do some races and jumping jacks on the grass, just to get their blood flowing. Getting enough sleep at night is really important too! Staying up late then getting up early will take its toll quickly, so try to only do one or the other.

One of the best parts of a road trip is the food, from po' boys to beignets to a classic crawfish boil. Try it all!

10. Eat well

The best part of a road trip? Definitely the FOOD! We took a cooler along filled with drinks, easy breakfast items, and sandwich fixings. This allowed us to save some money by eating “in” for two meals a day, then splurging on regional specialties whenever we could. We enjoyed Shrimp Po’ Boys at Pirate’s Cove in Mississippi,  Beignets at Cafe Du Monde in New Orleans, barbecue at Corky’s in Memphis and Jack Stack in Kansas City, and pizza at Home Run Inn in Chicago. But honestly the best–and downright incredible–meals (Bourbon glazed ham! Low Country Boil! Shrimp & Grits!) courtesy of our awesome, talented, and amazingly hospitable friends.

Granted after 29 days of really good eating, we are now in full-blown diet mode! Oh, but those 10+ pounds were worth every calorie! 🙂

The Best Family Road Trip Ever. (10 ways to truly enjoy the journey) Great tips and awesome insight from our 29 day, 4,000 mile road trip with the family. Don't even think about planning a road trip without reading this post first!


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