7 Lessons I’ve Learned Road-Tripping Across the U.S.

I absolutely love travel. Maybe it’s because my parents prioritized it when I was a kid –whether it was a trip to Disney World or my dad taking us through the woods off the sidewalk path in local parks. Regardless, I love exploring new places.

I especially love being in a foreign place. A language I don’t understand, food I don’t know how to pinpoint the ingredients for, and people who look differently than I do. When it came to traveling, I often flew to new places that were walkable because I didn’t have a car myself. When I purchased my first car after graduating college, I packed up my belongings and set off on a drive from Dallas to Massachusetts with my dad.

My dad and I’s first stop on our road trip up to MA: Hot Springs National Park in Arkansas. This overlook hike is a must on your visit!

The drive itself takes a little over a day, but we split it up over a few days, staying in national parks along the way. Since then, I’ve ridden an Amtrak train from Denver back to Massachusetts, driven all around New England, and made my way around the U.S. on three longer road trips (to Missouri, Georgia, and Montana).

In all those hours spent in the car and the days spent on the road, I’ve learned a lot about preparing for a trip.

A trail view from Voyageurs National Park in Minnesota on the return home from our road trip last summer.

Here’s what I’ve learned from road-tripping across the U.S.

1. Things will go wrong with the perfect itinerary.

Anyone who knows me knows I’m a big planner. I use a color-coded Google sheet with multiple tabs varying from transportation, to housing addresses to packing lists, and sights to see. I love knowing I’ll see most of what a place has to offer by planning in advance.

However, there are things you can’t plan for. You can’t plan for forest fires to bring smoke to mountain ranges from the state over. You can’t plan for your pre-made food to go bad because the outside heat melted your ice sooner than expected. Since then I’ve learned to not pre-make several servings of mac and cheese to save time later since we ended up throwing it away.

Tip: Make a list of your non-negotiables, meaning the things you must do or places you absolutely must see. If you want to see the Mesa Arch in Canyonlands at sunrise and it’s an absolute dream of yours, then make that a priority. Maybe skip another attraction, or grab breakfast instead of cooking it if you’re short on time. Take out something in your “nice to do” bucket to ensure you fill up your “must do” bucket.

A year and a half ago, our flights to Kansas City were canceled due to the weather in Boston. We rented a car and turned the Conference Championship game into a road trip. A perfect example of how we couldn’t stick to the itinerary, yet it turned out to be an amazing weekend. We were even able to make it to Cuyahoga Falls in Ohio and the Gateway Arch in St. Louis since we drove!

2. Always add two hours to your estimated time of arrival on your GPS.

You can’t plan for NY/NJ traffic to add two hours to your drive. Okay, maybe you can because it always feels like driving through this area adds so much time.

This is just one example of something that’s gone “wrong” on my trips in the past, or not according to plan. I’ve learned to add about two hours to the GPS. You don’t realize how much time you actually spend getting gas, buying an extra snack, and using the restroom even though you thought it’d be a quick minute to use the bathroom.

3. When planning, add in filler time. Or be okay with taking a detour.

Since we’re on the topic of time and planning, it’s important to add in time for the unexpected. On one of our trips, we were driving through South Dakota and saw sign after sign for a place called Wall Drug. The signs were such a hoot, we detoured and stopped by this tiny little western town. It ended up being one of the highlights of our drive through South Dakota! Had we not planned for additional time to get to the Badlands, we would’ve felt a need to stick to the road. Thus, missing this cool little spot.

When we made it to the Gateway Arch, our only plan was to view it from the exterior, take a few pictures, and continue our drive to Kansas City. We decided to take a detour, head inside, and book the last tour of the night. The tour took us up to the top of the Gateway Arch for this incredible view for sunset and back down in forty-five minutes. Totally worth it.

4. Double check your bookings a week before your trip. Or at the very least, the night before.

You may have planned to hit the road at 10 AM as soon as you pick up the rental car. That’s part of your itinerary, so it only makes sense. That is, until, you arrive at the rental company and they tell you you booked your car for the day before and since you didn’t pick it up, they rented it out to someone else.

Turns out, you aren’t leaving at 10 AM as you planned. This could have been easily avoided if I checked with the rental company a few days earlier to confirm the dates, or reviewed the booking email confirmation. This also goes for any boat tours or planned excursions you have, along with any campgrounds you reserved. Last summer I mixed up the dates more than once, which left us car camping under the stars in the Tetons (not mad about it), but it meant our KOA campsite in Yellowstone was given to someone else so we didn’t have a home base in Yellowstone.

Here’s the view from our campsite in Yellowstone, overlooking Yellowstone Lake. Not the worst way for plans to go when you mess up reservations.

5. If you’re using a rental car, get the insurance.

Everyone tells you this and you never listen. And when I mean you, I mean me. Almost everyone I have talked to about road trips says nine times out of ten, their rental car was fine. However, there’s always that one time. Ask anyone who travels on the road and they’ll tell you the trouble they had with their car or the animal encounter they had that no one wished for.

This goes back to earlier where I mentioned you probably won’t remember paying for things you forgot to bring. You won’t look back on your road trip thinking how much money you wasted on insurance. I add in the insurance when budgeting so that I don’t get overwhelmed when it comes to the total cost of a rental.

Tip: Book your rental in advance. If possible, pay upfront so your rental is reserved if you’re late and the cost is often cheaper. I use websites like Priceline to find the cheapest option. I also always double check for two things: 1) unlimited mileage (almost all rentals are, but vans/RVs often charge over 100 miles/day) and 2) restrictions.

More on restrictions - In Maui, most rental car companies don’t cover you if you drive a specific part of the Road to Hana. On a map, that part of the road looks like it saves you a great deal of time, but the conditions aren’t ideally suitable for driving.

On the Big Island, companies also don’t cover your drive to the summit of Mauna Kea. Always read the fine print or simply ask the representative which roads or attractions may be off limits to not lead to financial issues later.

 6. You will forget things. Just buy it along the way!

I used to get so stressed about forgetting something, as if there wasn’t a store along the way at some point to pick it up. In the grand scheme of your road trip, one purchase of q-tips won’t break your budget, and you surely won’t remember spending the money on it in the long run.

My very first road trip with my dad across Texas heading toward Big Bend National Park back in 2016. It’s safe to say I’ve been enjoying these drives for quite some time.

7. Embrace life on the road.

What initially was frustrating about mixing up dates and losing out on a campground in Yellowstone led to us finding out that each day Yellowstone offers first come first serve campsites. Had we had our original campground, we never would have landed a campsite directly across Yellowstone Lake, waking up to neighbors like elk casually walking past our tent.

Tip: Talk to locals or park rangers when visiting somewhere new. We pulled over to ask a ranger about campsites to snag the one I mentioned above.

These are just a handful of the lessons I’ve picked up driving across this beautiful country, and I’m sure there are plenty more for me to learn.

What lessons have you learned while traveling? Would you add any to this list?

Planning a Trip to Hawaii

How to Plan a Hawaii Trip: 4 useful tips to get started planning your island getaway!

1. Narrow in your days.

As a teacher, I’m limited to what times of year I can travel. However, that isn’t the case for everyone. Consider if you can possibly fly out on a Thursday, when flights are cheaper. Gauge whether you will need time to recover from the time changes and consider if a night in California is affordable and worthwhile for you. It turned out that our flights were cheaper if we flew direct to California, stayed the night, and flew out the following morning. A win-win.

2. Map out your experiences.

We knew we wanted to bike down from Haleakalā National Park in Maui, but we also wanted to night dive with manta rays on the Big Island. These excursions are not offered daily, so we needed to map out what days and times they were offered and go from there.

My favorite way to map things out visually is with Google sheets. I have used the same template for trip planning for a few years now thanks to a tech savvy friend of mine. Here’s what our first two days in Maui looked like, mapped out: times, dates, experiences included.

If you’re interested in the template above, subscribe to my blog at the bottom of this page, and I’ll send you my template for free!

3. Read up on safety precautions.

Since we’re still living in a Covid world, it’s important to minimize any surprises (some are inevitable!) while traveling. Going into Hawaii, I knew we would need a negative Covid test to enter Maui. Here’s what we needed to do:

• Create a Hawaii Safe Travels profile.

• Enter in all the information for where you will be staying. Since we were island hopping, we spent a bit of time entering all of this in.

• When booking a Covid test, we read through Hawaii’s Trusted Partners to determine which ones were close by. We landed on CVS because of convenience, but it did cost us $139.

• After receiving a negative test, we uploaded it to the Safe Travels profile. The website suggests you print a copy, but I strongly recommend you do. If for some reason your QR code doesn’t get sent to you (which it did for one of my friends), then the printed negative test allows you a stress-free passage through.

• Finally, 24 hours before your departure to Hawaii, fill out the pre-travel form and you’ll receive a QR code. Save this email or screenshot it for easy access when you land.

• That’s it! Unless you are island hopping. If you’re staying in Oahu the entire time, you’re good to go. If you are going to Oahu after another island, you’re also in the clear. If, like us, you decide to go elsewhere, like Big Island, we needed another negative result within 72 hours of departing to Big Island (meaning our original negative results to Maui would no longer suffice). We budgeted and booked time in our itinerary to take a CVS test while in Maui.

*This post was written in early May, after a week spent in Hawaii at the end of April. Hawaii officials are in talks about a vaccine passport, which would allow mainland travelers to bypass several of the above protocols. During my trip, this was not made official yet. *

4. Leave room for unplanned adventures AND for driving time.

We wanted to visit a black sand beach in Maui, but it didn’t work out, so we added one in last minute in Big Island (pictured above). My next tip is to leave time in your itinerary for unplanned adventures like this one, and for driving from place to place.

One thing we did not realize when booking airbnbs is the distance to what we wanted to do. On Big Island, we had this incredible, off-the-grid Airbnb right outside Volcanoes National Park. The only setback was that our manta rays excursion and the airport we were flying out of were two hours away.

If we had done more research, we would have stayed in that Airbnb for one night to explore Volcanoes National Park, then stayed near Kona the next couple nights to save on driving time.

Lastly, leave room for the unexpected: someone wants a snack, a picture, a pee break. It all adds up, so be sure to leave time in your itinerary for these little stops that often are forgotten about until it’s in the moment.

I hope these tips help you plan your adventure to the beautiful islands of Hawaii! Stay tuned for the next few posts where I take you with me into craters, volcanoes, and underwater. Subscribe to my email list below to be the first to find out when I post!