How to Plan a Road Trip
Hi friends! How have y'all been? Y'all been well? Y'all been coming back to this page every few weeks to watch our trip video? Is that just me? Nah ok cool cool cool.
Anyway kids, it's that time of year again. The heat index in DC is ten billion degrees. We are deep into a short and busy offseason (after a VERY EXCITING POSTSEASON for the CAPITALS) at work. I grow exceedingly tired of doing nothing with my life but working, working out, working out what shows I want to watch on Netflix, and sleeping. It is time for us to plan our next road trip!
I think somewhere around 20 minutes into the trip last year, Dyl and I made the decision that we would probably have to do this every year, likely forever. Even reading back over our posts and seeing how much we did and didn't get to do, the trip was one of the most life-changing and euphoric experiences of my life. Blame it on my parents; I was given the gift of travel at a very young age and have rarely shied away from a new adventure in a new place. So once we got a taste of travel on our terms, how were we supposed to stop?
Deep into the throes of planning this year's trip, I figured I'd share with y'all a little bit about the process we go through in putting together a cross-country road trip, as I have now done it once before and therefore am officially an expert on the topic. It really can be intimidating not knowing where to start, especially if you have time restrictions, are traveling with a dog, have no clue where to go, or any other thing that can make planning a road trip more complicated. It's a lot of information -- I am many things but brief is not one of them -- but hopefully it'll give you everything you need to know to plan a road trip. Here's a little list of a few things I go through and a few pieces of advice I can offer to anyone interested in taking valuable attention away from me by getting in their car and seeing some cool shit of their own ☺️ (I am kidding, honestly everyone should do something like this at least once, it will wreck you in the best way).
1. Check Your Calendar
Your calendar determines three main factors of your trip -- where you can go, when you can go, and how long you can be there. Knowing how much time you truly have is absolutely key. I'm fortunate enough to have a generous vacation policy at work and to love my job enough that I never really use it. I am a hoarder in most things in life and vacation time is no different. Dylan, however, has a very traditional two weeks of vacation and his work can be a little more strict about his time off, so it's important to us that we keep our trips in a two-week window.
Fortunately, we live very centrally on the east coast, and we know from experience that we can do a loop around most of the country in a two-week span. However, two weeks coast to coast still puts your Oregon Trail pace at grueling. It's very feasible if you do what we did and plan to spend no more than a day in each location, but just know... it's a fast pace. We averaged 7-8 hour drives, maxing out at our deeply traumatic 14-hour trek through Montana. The pace and time in each location was generally enough, and we managed to fit most of what we wanted to do in the afternoons when we arrived in a new location. There were times, of course, where we had to cut some things out in order to make it to other things, like ditching Yellowstone so we would have light in Bonneville. There were other times that nature cut things out for us, like when the gates of hell opened inside Glacier, and it wound up working out. The beauty of a road trip is that you'll probably be seeing enough awesome stuff that missing one thing won't totally ruin everything. Ultimately for us, the pace worked...but it's not for everyone.
Branching off that, it's important to figure out when you can go. As I touched on in my very first post here, as an employee of a professional sports team I have a very short window of when it's a good time to take an extended vacation. On top of that, we're traveling with a dog, which is extremely significant when it comes to time of year. On top of that, we have two weeks to cross the country and come back, so we need as much light as we can.
Last year, going in September made the most logical sense for us and the things we wanted to see. I wanted to see Lake Louise not frozen (no spring). I wanted to see snow (no summer). I also wanted to travel northwestern National Parks while the roads were still functioning, since many close in mid-late October when the weather turns (no winter). Since we knew we were going to be in the south and southwest and traveling with a dog built to herd sheep in the plains with the fur coat to match, summer was almost entirely out of the question for us. (Also summer is the worst and everyone is on vacation and we're very sweaty people.) It is absolutely invaluable having the peace of mind that G would be ok in the car for 10 minutes if we had to run in somewhere to grab bagels or something. Finally, the days were still long enough in the fall that we would still have a substantial amount of daylight to do everything we needed to do, which is especially important considering you're spending 8 hours in a car every day. Your needs and wants may definitely vary! For us, fall is the superior season for road trips (and literally everything else).
2. Use Technology
We are extremely #blessed to live in a society so technologically advanced that planning an elaborate road trip can be as easy as scrolling your Insta feed until your fingers fall off. That being said, I plan every location I want to visit on a trip through Instagram, Google Maps, and Buzzfeed. If your road trip goal is to see cool shit, all the cool shit lives on Instagram. Get scrolling. Find inspiration from bloggers and photographers whose job it is go to cool places and share it with people. So many of these influencers aren't only advertising their hiking gear and their Sony cameras (since when did everyone go all #AlphaCollective btw?), they're advertising locations too. Most photographers have locations geotagged. If you see something awesome, tap the location. Does it fit on your route? Can you make it fit?
Once you have a handful of places in mind, I usually flip to Google maps to get the numbers down. I start by picking two points on the map and seeing how long it takes to drive them. I like to use Google's "leave at" setting to see what the time is like around 6-7am, where there won't be so much traffic, since checking at whatever time of day it is at the time can make travel times less accurate. If my two cities are longer than around 10 hours apart, I start to look for any points of interest that might exist in between them. Literally by zooming in and seeing what cities show up first. This is how you can wind up in the most random places, but oftentimes they're super fun -- like sneaking onto the field at Oklahoma and then spending the night eating college pizza at a casino. Just be open to whatever makes your trip the most manageable!
As a general rule, I try to stick to 8 hours or less for most drives. You have no idea how fast a six-hour drive will feel once you get out there on the road. When you start getting more west, and things are farther apart, some long drives are necessary. One, maybe two excruciatingly long days are not the worst, depending on where you plan them in your trip. 10 hours on the same southwestern road with no other cars and an 80mph speed limit can feel like a breeze compared to 5 hours of bumper to bumper traffic once you cross back into eastern time.
Google maps only lets you plug in 10 locations at a time. However, you can make custom maps in Google Drive that allow you to stack multiple 10-location trips all in one map, which can be really helpful for visualization.
Once I have a general route, if there are some cities on it that I've never been to and don't know too much about, I flip back to social media. I check the Instagram geotag for the city, which on occasion will pull up some good stuff. Since geotags can be so specific though, and I don't know anything about the city, I don't always know what to search for to find the coolest thing (the geotag Banff, AB won't have photos of every cool lake and mountain, they'll be tagged under their specific location). That's when I usually go to a listicle site like Buzzfeed for inspiration. Searching locations there or even just browsing articles and videos can really help with finding cool stuff -- a Bring Me video is how we found Can Can Wonderland last year, which was awesome. Thrillist is also good for this, especially specific to cities. Finally, since food is vitally important, I search local foodies' instagram accounts for delicious looking things I want to eat in each city. Sometimes you'll get lucky and something will just pop up on the front page of Yelp, too, which is how we found Revival in Minneapolis. Long story short, the internet is your friend here. Use it!
3. Start Saving. Now.
This is the least fun one but probably the most important! Start a trip savings fund now. It's easy to trick yourself into thinking a road trip will be cheap because you're just driving around in a car, not flying, not necessarily staying in fancy hotels. But the costs really do add up when you think about it. Even with good gas mileage, you're probably filling up your tank at least once a day. You're eating out most meals. You need different lodging in every city. Not every attraction is free.
Last year, we invested in an America the Beautiful pass, which was only $80, lasts an entire calendar year, and afforded us entry to many National Parks we had on our list. We bought it at the Badlands -- I highly recommend waiting until your first park to buy it, since the longer you put it off the further into the next year it lasts. When we decided to invest in it, we had 4-5 National Parks on our list that added up to about $125 in entrance fees, so it made sense for us. When it came down to it though, it's not valid at Mt. Rushmore, Glacier was closed, we skipped Yellowstone and Grand Teton, and didn't wind up fitting Arches in, so we basically spent $80 to go to the Badlands. Lesson learned, but if you have a good amount of parks on your list this is a great cost-saving measure.
Last year we traveled during Canada's 150th anniversary, when Parks Canada allowed free entry to all of their national and provincial parks. I would not recommend waiting until their next national anniversary, so park entrance fees in Canada may apply too if that's where your trip takes you.
Before our trip we looked into a lot of apps with the purpose of finding affordable gas, but when it comes down to it, we never really wound up using them. As an east-coast native, I tend to operate under the idea that it's impossible to go more than like, 20 miles max without seeing an exit or a gas station on the road. Out west, that does not apply. I was truly baffled at how much nothing there was in Montana and South Dakota, and it definitely gave us a scare more than once that we'd run out of gas before finding somewhere to fuel up. Instead of trying to be strategic and buying gas only at the cheapest locations, buy gas when you need it and invest in a good rewards credit card to put it all on. You'll be happier spending a few more dollars and reaping the rewards than you will trying to contact AAA to get you gas when you don't have a cell signal.
4. Consider Your Lodging
Lodging is probably going to be your biggest expense on the trip next to gas, so if cutting costs is important to you, this is a place to start. We were really fortunate on our first time around -- Dylan had friends and family in many of the cities we stayed in, and staying with them helped us cut a ton of costs. We also had our parents contribute nights of our hotel stay as birthday presents and just because they're great parents. This time around, we're more on our own, so we're trying to be a little more frugal with our stays.
On the note of planning lodging in advance vs. going where the wind blows and stopping when you're tired: it's not for us. We move at such a fast pace and we travel with a dog; if we don't have the appropriate accommodations in the locations we need them when we need them, it could screw up the entire trip. We try and start booking lodging 2-3 months in advance because 1. It's committing to a plan 2. You can shop around for the best price and 3. It helps narrow down your route.
When looking for lodging, especially Airbnbs out west, I'm really flexible with location. I may have Bozeman listed as a stop, but if we find a cool place to stay a few miles or an hour away and it still fits in the route, that's totally fine. That's the new stop, and the trip can work around it.
Since we travel with G, it's easiest for us to stay largely in Airbnbs. Many Airbnb hosts are open to dogs, especially when they meet G and realize how chill he is. While there are tons of pet friendly hotels and motels, the fees associated with bringing a pet in a hotel can be totally astronomical -- up to $100 in a lot of chains, which is more than we even want to spend on a night's stay alone.
We know us, we know what we need. We like nature but we're not campers -- we literally don't know how. We have a live animal with us and we're scared of bears and the cold. I like falling asleep with the TV on. We're also in our 20s and don't have piles of money to spend on the most luxurious amenities. We find Airbnb the most cost effective for us, and oftentimes we wind up having really unique or special experiences with our lodging and hosts (shoutout to our Santa Fe Airbnb hosts, y'all were all time). Our standards aren't so oppressively high that we're too bougie to crash in a Motel 6 for the night either. The important thing to remember about a road trip is that it's about the things you see along the way. Your hotel is not going to be the focal point of your vacation. It's just a place to lay your head.
That being said, we do like to incorporate a splurge on a nice hotel or unique location once or twice on the trip because we're worth it and staying in strangers houses can get exhausting.
5. Plan, Be Flexible, Be Honest
Once you have an idea of where you're going, how long you're gonna be there, where you're gonna stay, and how you're gonna pay for it, you can get down to the nitty gritty. Start planning specific activities to do and landmarks to see. Think about your driving times, when you're going to leave and when you're going to arrive on each individual day. If you're crossing the border with an animal, make sure to request all the appropriate paperwork from your vet. But once the details are down, remember to just be flexible and honest with yourself.
It's like the number one rule of both road trips and life, but it bears repeating yet again. You can plan as much as you want, but nothing is going to happen exactly how you think it will. It's important to prepare yourself for the unexpected and be ready to go with the flow. Did I know when we got to the treehouse in Montana that there would be no shower, no mirror, and a foot of snow on the way when we had to get photos done in Utah that afternoon? Did I know when we stopped at a Chili's in Helena that I would wind up locked out of our car with G for 45 minutes in the cold? Did I know it would be 95 degrees in Chicago and 25 in Canada three days later? Nope. But you deal with it, you roll with the punches, and you move on.
Flexibility is important, but being honest with who you are, what you need to be comfortable, and what you're capable of is paramount when undertaking something like this. I touched on this earlier, but to get into more detail, it's really important to know how you want your trip to go, and not base it on anyone else's choices or experiences. We're fine in motels and airbnbs. You may not be comfortable in that situation and prefer top-of-the-line accommodations. Or you may love nature or the van life and be tight with bugs and pooping in the woods.
At the beginning of our trip, we were so sure we were gonna save on food money by stocking up on groceries and filling the car with bread, peanut butter, and protein bars. It was noble of us, but in reality, we like fast food and we are perfectly ok beginning each morning with a bagel and an iced coffee -- so we did. Not everyone is trash people like we are and can survive that way! We however, can and did. I personally am still trying to get through the box of quest bars I bought for the trip.
All of that is ok. Just cause we're broke, scared of bears, and addicted to Starbucks doesn't mean doing something a different way from us is wrong. Just be true to yourself. Don't plan multiple 10-hour drives if you hate driving and just tell yourself you can get through it. Don't lie to yourself about eating healthy and working out on the trip if you know you don't want to prioritize that. Don't think you have to travel a certain way just because that's how someone else is doing it.
6. Travel with a Partner
The biggest running joke of Dylan and I going on this trip together is would we kill each other before we hit Canada? I think we were both nervous about that going into it, but it honestly worked out so well for us and I really do believe it brought us closer together.
Aside from us generally tolerating each other, our personalities mesh in ways that are very important when you're taking on a cross-country road trip. We like the same podcasts (pro tip: stop listening to podcasts 3 months in advance so you have enough new content for the long drives; also Casefile is the best true crime podcast and it's not even close), we both need morning coffees to function, and the excitement from traveling to a new place every day is enough to keep us both in really great spirits. He is a ferocious overpacker while years of traveling standby has trained me to pack as light as possible. He'll take over after I start falling asleep an hour into my morning shift, and I'm fine driving the night shift through the rain. Also, he has AT&T and I have T-Mobile, so I have cell service in Canada and he has it literally everywhere else.
I had aggressive amounts of anxiety about being sure I would have the right clothes for the trip, since we had the potential to hit so much weather. I literally gave myself analysis paralysis over it and just wound up convincing myself we would be fine because the coldest weather we saw forecasted was the high 50s. I should've been honest with myself, but I am delusional and stubborn, so I wound up WRONG AND COLD, and if I didn't have boots from Sylven I would've been freezing there too.
So, my final piece of advice is to travel with someone who is truly your partner, someone that balances you out, and someone that packs three winter coats when you pack zero.
If you made it this far THANK YOU, and stop enabling me. This is officially everything I know about planning the ~Great American Road Trip~ and hopefully it helped you get a clearer picture of what goes into making it work!