Road Trip Planning 101

I love planning vacations, particularly road trips. It’s so fun to look at a map and see the possibilities of educational and entertaining stops along the way to your final destination.

I didn’t grow up taking long road trips. Our longest trip was from our home in North Carolina to Disney World when I was ten years old. Most of our vacations consisted of 3 hour drives to the beaches of South Carolina or to visit relatives in Georgia. I’m jealous of those who took super long cross country road trips in their youth. It sounds so fun!

On most trips, I read in the backseat for the entire trip. When I was in my early teens, my mom handed me a road atlas and told me I needed to start paying attention to where we were going. I’m so glad she did, it instilled a love of maps in me that I still have to this day! 

Planning road trips can be easy – go from point A to point B and done. But if you do that, you might miss some of the amazing things along the way! I’ve put together a few tips that help me when planning a road trip whether in America or abroad. I’ll give some concrete examples using our recent Deep South road trip planning.


  1. When deciding on your final destination, look at a large map. Plot several routes there and avoid retracing your steps to ensure the maximum amount of new territory covered. Note if you’ll be near any must-see places you’ve always wanted to see. If you’re flying to a destination and then doing a road trip, be sure to investigate flying out of a different airport. That way, you won’t have to double back!

When planning our recent road trip, our main objectives were to visit both Seaside, Florida and the Delta Flight Museum in Atlanta. While plotting our route, I began to visualize the large loop we could do to get there and back, taking us through several historic cities and sites that were on my to-visit list. 

Our final route (Image taken from Google Maps)
  1. After deciding on your destination and the amount of time you plan to travel, use Google Maps to plot several different ways to get there using driveable segments. We’ve found that planning for 6 hours of driving is about all we can do in a day as a family. Your family’s tolerance may be shorter or longer but don’t forget to account for time spent at stops along the way. Also look for interesting drives – sometimes the shortest way isn’t the most fun. 

For the first leg of our trip, we were headed to Nashville from western Virginia. Google Maps gave me several different options, the quickest being I-81 through eastern Tennessee. But it also showed me that going through Lexington, KY was only 30 minutes longer. Since we had always wanted to visit the University of Kentucky, we made the decision to go that way. I never would have thought of that route on my own.

Image taken from Google Maps
  1. Plot the major cities or sites you’ll go through and begin your deep dive. 
    1. Visit the city’s tourism websites or trusted family travel sites
    2. Buy a guidebook about the destination. For US travel, Fodor’s, Frommers, and DK usually have good guides. For travel in Europe, Rick Steves is the ultimate authority. 
    3. Google “best historic sites/museums in XXXXX” or “family activities in XXXXX” 
    4. Use Google Maps and zoom in to see what it highlights
    5. Employ a travel agent to get access to vetted lodging and private tours/activities. We love our agent, Katie Brown, from Ciao Bambino
    6. Check out Historic Hotels of America to find unique, non-chain hotels 
    7. And of course, consult The History Mom using my destinations link and my Presidential sites checklist 

I’ve found some of my best stops using Google Maps. When looking for UK’s Rupp Arena in downtown Lexington, I stumbled across the Mary Todd Lincoln House right next door. 

Some of our best experiences on our travels have been the private guided tours set up by our travel agent, Katie. Much better than the crowded tours you’ll find at touristy spots.

  1. Start a Google document to keep all of the information you find in one place and which can be shared among family members. I’ve tried apps that do this but a Google doc works best for me since it’s easy to make changes and flip things around if needed. Once the trip is planned, I print this out and attach all of the tickets, brochures, etc. for the trip. Go with what works best for you but make sure to have all of the information available in one place.

I create a massive Google document where I list: 

*day and date (e.g. Day 2 – 7/5 Monday)

*destination and driving time (e.g. Nashville to Huntsville (2 hours) to Birmingham (1.5 hours)

*potential hotels, restaurants, and sites of interest (be sure to include hours of operations, especially during COVID)

As your plans finalize, you can add in hotel confirmation numbers or times of tours.

  1. Once I have a better idea of the plan and activities, get your family involved and put a family member in charge of one aspect of the trip. Let your kids explore the tourism sites with you and talk about what they want to get out of the trip. I usually take care of all of the historic sites or museum research but I need to find out what my husband and kids want to do outside of those. I print out my Google doc and let them add or delete items.

For our recent road trip, I put my husband in charge of the restaurant selection in New Orleans so that meant I didn’t have to do all of that research. My older son’s main requirement was beach time so I made sure we had three days at the beach.

  1. For road trips, it’s easy to think you’ll want to add in one more stop or museum. Or that if you’re driving by an attraction, you have to stop. More is better, in my opinion! However, in practice, I’ve found that it’s best to build in rest time or hotel pool time, especially with younger kids. I’m the type of traveler that always wants to be on the go, fitting in all of the historic sites and museums a city has to offer, while my kids can’t bear to spend all day touring – even as teens. It’s hard for me to hold back and not push but I try to keep in mind that this is their vacation too! Trade off with your spouse and take a solo excursion to that museum you’ve been eyeing. Or keep in mind you can always come back!

In Nashville, our kids just wanted some downtime in the room. After an hour of that, I was antsy so my husband and I visited the Tennessee State Museum on our own (it’s much easier to do this when your kids are old enough to stay by themselves!).

It was hard for me to hold back from trying to squeeze in every historic site on our trip. During our drive from Nashville to Huntsville, we drove right by President Polk’s house but didn’t stop. And I had planned a day in Mississippi to visit the Vicksburg battlefield but we decided it was just too much driving. I had to tell myself that I’d be back – someday! 

  1. My last piece of advice – go with the flow. As a planner, this is the hardest thing for me to do. I like to keep to a schedule and itinerary – and with some vacations like Yellowstone, you have to plan so far in advance that you can’t wing it. However with most road trips, you can leave a little up to how you’re feeling that day. That’s the one big advantage road trips have over flying – flexibility.

The last two days of our road trip ended up changing at the last minute. I had planned and planned but in the end, we were tired and just wanted to get close to home. Those last two hotels ended up being our favorites, even without the extensive research I usually do!

Road trips can be fun and give you lots of fun family memories. Let me know in the comments your best tips and some of your favorite road trip itineraries!

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