Is there anything more idyllic and bucket-listy than a road trip? I recently posted a few pictures from our road trip last summer which was a two week, six states, road trip with a four-year-old and one-year-old. A question I was asked a lot through Instagram direct message was “How did we plan our road trip?” and “Where did you start?” Of course, that was followed by many people asking how we managed two weeks on the road with the little ones. Admittedly, planning a road trip can be daunting, but it is easy once you get started. Below you’ll see how we planned our road trip, and maybe it’ll encourage you to plan your own! We absolutely loved our trip, and it definitely inspired us to do it again this summer!
This is the first post of a series explaining how we went about planning our epic, two-week road trip throughout the South. Over the next few weeks, I’ll get into the nitty-gritty details about our adventure including how to plan, what to pack, how to survive two weeks on the road with kids, and some of our favorite stops along the way. Today, I wanted to talk about transitioning from the hypothetical road trip so many of us talk about to actually planning a road trip for real. It was a fun and exciting time for us with weeks of revisions, but ultimately it set us up for so much success.
What made us actually check this off our bucket list
We do the same vacations every summer. We go down the Jersey Shore and go up to the Pocono Mountains; we adore both of these places, but our world was feeling rather small. We live in a county that people rarely leave. We didn’t have passports until our wedding for our honeymoon. I was never west of Pittsburg before our honeymoon and I only crossed that line for our honeymoon. Last spring, we took our kids to Disney World which was everything we imagined it could be and more. One thing we learned along the way was that we could survive traveling with our kids. Hypothetical road trip conversations happened shortly after.
My wife and I talked about going on a road trip ever since we were teenagers--where’d we want to go, if we could last in the car for weeks, if we’d be planners or just get in the car and drive, and countless other things without ever fully committing to going. After our Disney trip, still riding the high of successfully traveling with kids, we saw one of those travel shows where they talk about cities and their awesome food. There was an episode of Cheap Eats where the host ate his way through Asheville, NC, a magical Southern town I never heard of. That night, I fell down a rabbit hole of searching hashtags and Instagram posts detailing all the amazing things in Asheville while my wife scoured blogs and started daydreaming of adventures. By the week’s end, we were making plans. Real plans.
Planning two separate trips
My goals were to climb a mountain, eat BBQ that is real BBQ, and eat all the biscuits.
My wife’s goals were to swim in the ocean, see picturesque Southern cities, and eat all the biscuits.
My wife found the app RoadTrippers, which is an app made for planning idyllic road trips. You can chunk your journey and find places to eat, interesting stops, and places to stay along the way. We both downloaded the app and planned separate road trips with our family in mind; turns out, we both had different families in mind. My trip was centered around family hikes that were several hours long and required real training, BBQ joints that had long lines and were open until they sold out for the day, and other “authentic experiences” that were a little gritty or adventurous which were (in hindsight) terrible ideas for children. I really wanted to check out this old, abandoned mining town that is supposedly haunted, for instance. My wife’s road trip was more sensical but involved no mountains, no weird “for the hell of it” experiences, and no restaurants already mapped out--a lot of children’s museums, historical landmarks, and picturesque small towns. We compared notes and made compromises.
Being the teachers that we are, we planned our road trip much like we plan units for English class. We started backward and with the essential question: “What do we want from this experience?” While we still both had a few priorities for the trip, we went into it with an agreement that the kids were always first, and we wanted to give them a world much larger than what we were used to. We mapped out the cities, pitched each other stops, and made a vague map. That map would have taken 3-4 weeks, so we needed to edit, but it was a start.
Plan around your family, not the best version of your family
The trip itself was defined on compromise. I’m woodsy-adventurous and I am my most content hiking or on a body of water. My wife is not. She is not one for hikes and likes the idea of nature, just not having to be immersed in said nature. My wife is at peace in the shade, engaged in a learning experience, or relaxing near a body of water or nature. I am not. I cannot relax or sit still, and would sleep in a tent all summer if my wife let me. Sure, it would be awesome doing a five hour hike as a family to see breathtaking views of mountain tops, but we had A BABY AND A FOUR YEAR OLD. Our oldest can’t even navigate the living room for 30 minutes without injury, so I don’t know why I was thinking an actual five hour hike would be a thing. We all wanted to enjoy our trip, but we (I) needed to be a little more realistic.
When we both started being more realistic with our planning, we were able to whittle down our lists of things we wanted to accomplish on our trip while still being happy with the trip. I got some mountains, my wife got some culture, our kids had all the children’s museums, playgrounds, and swimming pools they could handle. Ultimately we ended up with a pretty awesome and fulfilling trip.
Planning a trip through Instagram
Okay, I know I’m a millennial. Aside from killing industries like the napkin industry and buying all the avocado toasts instead of houses, I used Instagram for a lot of my research for travel and food. It’s not to find out if it a place has good lighting or a big, bold wall to take a selfie in front of, but it is to see real world experiences from people who aren’t angrily shouting through online reviews. I see why people use Yelp, but I am not into it. There is a website where students can anonymously rate teachers or professors and it’s terrible. Teachers don’t sign up for it, yet students can anonymously post reviews of their teachers for the whole world to see. If a kid is going to create an account, verify their email, and write a review about a teacher, it’s either going to be a scathing or glowing review--never a “meh.” Usually, it’s negative because people don’t go out of their way to say positive things most times. I get the same vibe from apps like Yelp. If I am unhappy with a meal, I try to inform the manager so they can know and rectify it in the future.
Four Things I Look for When Planning Through Instagram
Instead of Yelp, I search for restaurants using hashtags like #philadelphia #philly #phillyfoodies #phillyfamily. Just replace Philly with a different city. Eventually you stumble across a couple of foodies and you’re bound to find some restaurants that way. Once I find a restaurant I’m interested in, I see if they have an Instagram account, see what people post when they do a geotag, and see what people post when they tag the restaurant. When I’m scrolling through pictures taken by strangers at restaurants I’ve never been to, I’m always searching for:
- If children are present - Family friendly is key because my kids are not the best at times.
- Dress code - We don’t bring our kids anywhere where it’s assumed men will have their shirts tucked in or women will be wearing heels and fancy dresses. This is also a good test to see if kids can come. I call it the sweat pants rule. If you can wear sweatpants there, you can bring kids.
- Menus with prices - I hate when places post menus without prices on their website (I mean, I get it, but still). Sometimes you can find a picture of a menu board or actual menu to help gauge prices.
- Different menu items - Nothing is worse than ordering food and it being a weirdly small portion or just something not at all what you hoped and dreamed it would be. Those of you with kids will also understand the struggle of ordering macaroni and cheese or chicken tenders to find they got extra creative with it.
I use the same strategy when planning activities for my family like hikes, museums, and other events. It helps you weigh options and plan accordingly. While our kids are pretty easy when it comes to adventures, we try to plan ahead to find out if things will be “worth it.” For hikes, similar to my sweatpants rule for restaurants, I’d search for small children and dogs. If dogs are capable of coming with, so can my kids.
Instagram Bookmarks > Your Mom’s Pinterest Board
If you are not using bookmarks in Instagram, you are not using it to its full potential. I started doing this when we planned for Disney, but it has become my own dream board of food and places to visit. Not only can you bookmark posts, but you can organize them into different groups. For the road trip, I organized my bookmarks into cities and stops along the way. By doing this, I was able to learn from other people’s experiences and plan my own trip around that. Why just follow food porn accounts if you never plan on experiencing the food one day? I still have countless posts for cities I have never been to, but one day I’ll get there and I’ll be prepared to gain ten pounds like a pro.
Here’s how you do it. First, find a post you love. You’ll see the little bookmark button above the caption. If you click it, you’ll automatically bookmark a post. If you want to organize your bookmarks, hold down the bookmark button and you’ll be prompted to put it in a folder. I organize my bookmarks based on cities, but that’s up to you. Another reason why I wanted to do it this way is because our kids and our interests were not things I could predict weeks out. Sometimes you just need something fast, other times you’re just not into the idea of tacos that you really liked a month ago. Having your own collection of visual options will allow you to be flexible but still in the know.
Go Make Plans!
We started planning our summer road trip shortly after spring break was over. If you’re reading this, go talk to your loved ones. Challenge them to make a road trip and compare notes. Get lost in a rabbit hole of hashtags. Our road trip was a life changing experience that we hope to do again this summer.
On my next post of this series, I’ll talk some of the prep work we did to get ready. We literally left the day after school was out for the summer, so we needed to be ready to go. We are also both type A people with over packing problems, a Subaru Forester, and a double stroller so important decisions had to be made.
