Road Trip Planner – An Odd Way of Planning a Road Trip

Written by: Greg Cayea

October 12, 2019


Road Trip Planner Driving Through Water

You don’t want some bullshit TripAdvisor forum tellin you where to go, right? Don’t you wanna hit the road and experience the thrill of getting lost in adventure the vagabond way? YES! That’s why you need a road trip planner that’ll spark inspiration to pave your own path.

I gotta an idea for ya. How about we plan a trip according to your personality? That way you won’t run the risk of spending valuable time visiting places you don’t give a shit about. This is the Vagabond Way – crackin open a fortune cookie that just might change your life…


Am I the only one that needs road trips to survive? Getting on the road is the best therapy I ever didn’t pay for and boy do I need a good dose of therpay every six weeks. Nothin gets me outta my ruts like hoppin in my car and driving somewhere strange; been doin it my whole life and now hold the Guinness World Record for Longest Journey by Car in a Single Country. How the fuck did that happen? Well… that’s another story you’ll find here. But anyway, during that trip and on the millions of road trips prior to that particular trip, I drove nearly every interstate and highway in America, going through hundreds of small towns and major cities all over the country. So, I’m a damn professional and I’ve always thought: Different people like different shit, right? I’ve always been obsessed with personality type tests… and I thought man, wouldn’t it be fun if you could choose your own adventure based on personality type?


Here’s what we did, we created an entire road trip planning post so that you can drive to the perfect place and find the perfect inspiration along the way based on what you like, where you’re going, your personality type, astrological sign (if you’re into that bullshit), how many days you wanna be on the road, how many hours you wanna drive per day, and your starting point–all that shit.

It’s all done, just for you.


Road Trip Planner Sports Car

ONE THAT GETS YOU OUTTA YOUR HEAD AND ONTO THE ROAD. I mean, no route is better than another, but every direction leads you somewhere different.

The saying, “Wherever you go, there you are,” is bullshit. I mean, philosophically I get it. Sure, if you have marital problems in San Antonio then they’ll probably still be there when you get to Greenland., but location does have a major influence on how you feel, right? How do you feel at the laundromat?

Now how do you feel at Thanksgiving dinner?

What about the dentist’s office?

All I’m sayin is that I don’t want to head to the Loneliest Highway in America (Highway 50) if I’m feeling disconnected, but I might wanna chill by Lake Tahoe seeking sexual relief. Is that a bad example? How about this… I don’t wanna be flooded with conversation at a New Orleans hostel if I needa clear my head and think, but a random truck stop outside Albuquerque where I can park my car, pop the back of my Subaru open, and stare at the stars till 1AM does the trick perfectly.

Can I ask you somethin?

Why you doin this? What’s the reason you wanna hop in your car and onto the road? Why not opt for some other way to spend your time? There’s a reason you want to take this road trip right now, AND I WANNA KNOW WHAT IT IS! Why? Cause that’ll dictate everything. 

My goal is to help you plan your road trip by making this process so damn fun that ideas you never knew you had will come outta nowhere.


Road Trip Planner Mountain Trip

To know how you feel right now and what you want from your road trip is the best way for us to get started. There’s a route for every mood in the atmosphere. To get started, I just need to know how you feel right now, your astrological sign, your personality type, and have your social security number. That’s a joke. You laughing? Anyway… Your inner psyche is the best road trip planner in the world and I’m gonna walk you through how to tap into it.


Gettin in your car without a clue of where you’re going is easy, I’ve done it a million times. But it can leave me feeling a bit empty when I scramble to find a motel in the middle of Utah at 7PM as the sun is setting without a clue of why I hopped in my car to begin with or why the hell I drove to Utah. Basically, when I drift aimlessly it feels off.

If you take a road trip because you think it’s the right thing to do, that’s a bad starting point AND YOU’RE ALREADY FUCKING THIS UP–sorry, I’m just kidding. You’re doing fine. But don’t try to take the all-American road trip cause movies say so. You’ll end up scarring your kids for life with terrible memories or setting a tempo for your vagabond lifestyle that says: I’m lost, and not: I’m fucking awesome and have true freedom.

Here’s what to do…

Wander with direction and know what you wanna accomplish. Here’s what I mean, know your goal! Like one of these might be close to it:

  • You want a great family outing
  • Need to get through a breakup/ divorce
  • Graduating school with no idea how to proceed in life
  • Losing a job and no idea what to do
  • Broke and need to save money on transportation to get to a destination
  • You want some kinda adventure in life
  • Quarter-life/ midlife crisis – I get these every few years
  • Romantic adventure with a lover or rekindle a romance
  • Testing out #vanlife to see if you’re cut out to live on the road
  • Thirst for meaning
  • Unhappy with life
  • Lonely
  • You need creative inspiration
  • You want a better Instagram profile than your friends
  • Seems like a great vacation
  • Maybe you wanna experience the unknown or what you don’t know
  • Personal growth


Road Trip Planner Open Road

Certainly you don’t just want to put miles on your car and spend money on gas to say you did a road trip. Whattaya tryin to do here? What’s at the end of the road trip rainbow? You goin skiing? National Park hopping? Hiking adventures? WHERE YOU GOING?

Of course just wanting to take a road trip is fair enough…

But we can do better than that. Wanna knock some bucket-list items off your notebook app? Go to every ghost town in America? Take a surfing road trip up the PCH? Have sex in every state? Go hostel-hopping and play music? We doin a photo shoot road trip? Is this a journalism typa thing? You need writing inspiration or what not? Maybe you need some Instagram content to make it appear like you’re doing better in life than you actually are, that’s cool too.

But we need to know where to go to make that facade appear real. Taking a photo in front of The Big Rig Doll House (a methed-out strip club) in Kingman, Arizona won’t impress the in-laws at all.

Know what you wanna do but not sure where you wanna do it? GREAT! Not sure where to go or what the hell you’re doing but quite certain you wanna be on the road and take a dope road trip? FANTASTIC! This is a road trip planning post so you’re in the right place. Keep reading.

I don’t know what I’m doin with my life

Road Trip Planner International

I hate when people say “focus on your goal.” No! That’s the point! I don’t know what my goal should be!

“Well what’s your passion?”


“Okay, well what do you want more than anything?”

I STILL DON’T KNOW! Those are my questions to begin with! I’m trying to find my goal or my passion or life purpose or whatever… I want to know how!

Here’s what helps me: I make lists.

I list out fifty items that I wanna gain in my life or that I would regret not doing, then I cross out ten of them, then another ten, then another ten, until finally I’m left with my top three goals. Then I stare at them and circle the one I want to achieve. After that, I stop thinking about it and just do it.

If you want a shortcut you can find your road trip route here, but I still recommend doing this exercise.

Okay now you design your dream trip

Write down fifty things that would be awesome if you did.

The first ten are easy, the next ten are a bit harder, then you’ll have no idea what to write, but keep writing. By the last five you’ll be writing the dumbest shit ever, but that’s okay, that’s where the magic happens.

You might end up with goals like: Become an American Ninja Warrior or make a movie about disabled squirrels or become a famous ukulele player on Youtube… whatever it is, well, that’s what it is. Just be honest.

They may look somethin like this…

Just to get your juices flowin, here are some random things I wrote down that sound pretty cool to me right now as I write this post. Don’t be afraid to start sounding nuts.

  • Go to every cattle farm
  • Take selfies with giant beetles
  • Collect national park brochures
  • Go to the top of every tall building
  • Explore caves
  • Scuba dive ten times in the Pacific
  • Live outta my van in Grass Valley
  • Snowboard everyday at a different mountain
  • Become a park ranger at my favorite park
  • Rock climb somewhere and do it again
  • Take surfing lessons with ten hot chicks
  • Get five rocks from the bottom of the Grand Canyon
  • Follow some shitty band on tour around the country
  • Become a local somewhere weird
  • Start a cult

That last one came outta nowhere, but anyway, let’s decide the best place for you to travel.


Road Trip Planner Lake

Okay, time to put in work and get wild. So many ways to make your life more interesting with road trips and so many ways to find the right spark to ignite your road trip blaze but here are a few. You can choose by adventure, region, astrological sign, Myers-Briggs personality type, or road trip theme.


Maybe I don’t know the end destination in the very beginning, but I know what type of adventure I wanna get into, and so should you. I like to keep some sort of goal in mind when I get behind the wheel. Or maybe I know exactly where I’m goin and wanna make it into a road trip even if it makes little sense economically. I always wanna make any trip into a road trip.

If I’m traveling to a conference for work across the country and I only have a week–I’ll STILL drive there. ROAD TRIP! Any time I can get on the road is a fuckin win. Maybe my girlfriend and I wanna take a vacation and the idea is NOT to do a road trip, but to do something else, like get a lodge upstate and be romantic and shit… I’ll STILL try to spin it into a road trip.

I’m addicted to the road.

Sometimes the only thing I know is that I wanna get in my car and go somewhere but I’m not sure of anything else. With all that said, here’re some ideas to spin your regular life into an exciting adventure.

Skiing or Snowboarding Trips

If you’re hopping behind the wheel to go skiing in Sun Valley or Jackson Hole, for example, and you’re leaving from Boston, you may want to hit up all the great ski or snowboard mountains along the way rather than just waiting till you get to your destination. This can make one ski trip into an entire ski adventure, whether you’re solo, with friends, or with the family.

Hiking or Camping Trips

Road Trip Planner National Park Road Trip

If you’re planning to hike Zion National Park and you’re leaving from Los Angeles or Dallas or wherever you’re leaving from, we’ve put together a fantastic road trip full of every national park in the lower 48 states that you can stop off at on your way to whichever park you plan to hike or camp at. Seeing all the national parks is a lifelong goal and you may as well stop off at the best parks along the way even if it’s just for a day hike or to drive through! It’s still worth it! Better than not going at all, right?

Music Festival or Concert Trips

Road Trip Planner Big City

I had a wild road trip on my way to Burning Man… so wild that I never even ended up going! That’s an entirely other story about my car being broken into in Montreal and my transmission breaking down in Kingman, Arizona.

The point is, instead of just Burning Man, I researched all the other festivals that were happening in the country during that time–festivals I would never go to if it weren’t for simple timing–and made a route around that. If you’re heading to Coachella or JazzFest then do a quick search to see all the other festivals happening around that time and see if you can hit more than one festival on your way there! Now that’s a road trip!

Work Trips

Let’s say you’ve got a conference you have to attend in Las Vegas or Aspen or Atlanta… Doesn’t really matter where you are. If you’d like to opt for roadtripping there rather than flying, instead of just stopping off at the Best Westerns on your way there, why not make it into a trip by stopping off at places you would never ever get to see if it weren’t for this work trip? That’s why you should have a good idea of the route you plan on taking wherever you’re starting to wherever you’re ending.


Let’s go over what each region of the United States has to offer. Here are the main sections of the country:

Here’s a brief breakdown of each of those regions (without going into too much detail yet).

Roadtripping the Southwest

Road Trip Planner Southwest Road Trip

You’ll find much solitude and time to think in this part of the country. If you like the open desert, dusty towns, and vast landscapes, the Southwest is where you want to be. This is also where you can squeeze in the most amount of national parks in the least amount of distance.

You might be thinking, well, there’s solitude everywhere… Sure, but there’s a big difference between the solitude you find in the Southwest and the solitude you find in the Rocky Mountains. In the mountains, you can’t see over the mountaintops that surround you and it feels quite snug.

But in the Southwest, I don’t feel a breath of life in any direction and the views are so vast it sends me chills of quiet. It’s the epitome of solitude.

Roadtripping the Pacific Northwest

If you’re looking for a getaway that’s not so isolated but still gives you a breather from society, head to the Pacific Northwest. This is probably–in my opinion–the most beautiful part of the country. The views are always scenic and filled with water and greenery and any trip in Washington or Idaho will give you enough Instagram content to last your great grandchildren a lifetime.

If there’s one thing the Pacific Northwest has that’s unique to the region it’s the rivers; they’re enormous, and they’re everywhere. If the color of the Southwest is dusty red, the color of the Pacific Northwest is turquoise green.

Roadtripping the Mountain Time Zone

Road Trip Planner Mountain Trip

If you’re looking for adventure, from Montana to New Mexico, the possibilities are endless. Kayaking, white-water rafting, hot air balloons, skydiving, horseback riding, skiing, snowboarding, mountain biking… it goes on forever; it’s nature’s playground.

But what I like most about Colorado and Wyoming and Montana and New Mexico are all those small mountain towns and wild wild west towns you stumble upon after miles of twists and turns up peaky mountains. I love going from a low elevation to 8,000 feet in a matter of hours.

Quick tidbit

Beartooth Mountain Pass is my favorite road in America, and you’ll find it at the exit of Yellowstone in Wyoming leading into Montana.

The hard part about this region is some of the roads are so windy it takes an hour to drive twenty miles. Plus, there’s nowhere to pull off and sleep if you’re car camping. Sometimes you’ll have to drive a long distance before finding anywhere to pull off and sleep.

Roadtripping the West Coast

I lived in Los Angeles for about six years and I can tell you that driving the Pacific Coast Highway (PCH) never gets old. I’ve driven that road (a mix between the PCH and Highway 101) starting on the boarder of Mexico and taken it up to the border of Canada and there’s not a road in the country like it.

I find it better to not take the coastal route for the entire trip if you opt for this route because you’ll miss some amazing stop-offs. You’ll have to drive inland for a bit every now and then to get to some of the awesome cities like Eugene and Portland.

You’ll start in San Diego and hit Los Angeles and then Santa Barbara and Big Sur, which is probably my favorite place in the country. Then you’ll hit San Francisco and up through the Napa Valley–but stop off in Grass Valley and–you know what?

Q: How do you sleep for free when driving the PCH since there are no rest areas, truck stops, or Walmarts? A: Just pay the parking tickets you get every now and then! It’s the cheapest way to car camp on the Pacific Coast! Click To Tweet

Roadtripping the Great Plains

There’re few characteristics that really stand out about The Great Plains. The first is the view. It feels like I’m driving on top of the horizon, and the sky looks like it’s sinking down on my face.

The second characteristic is the wind; it goes from zero to a hundred in millisecond and there’s nothing to shelter you for a thousand miles.

Quick Story

It was a dark and stormy night the night I made it to Williston, North Dakota. We couldn’t see shit as we pulled into a parking lot–or what we thought was a parking lot–to sleep for the night. The wind was blowing the car from side to side. It was so strong we had to setup the inside of the car without opening the doors. I tried to pee outside and the stream misted away the second it left my body.

We woke up the next morning in the middle of a random mud field. There was a small shop a half a mile ahead that served food. We ate at a place that felt like it wasn’t open for business and left. But I got off track…

The Black Hills of South Dakota is a deeply satisfying part of the country and one that many never see, except to see Mount Rushmore (and many forgetting that Crazy Horse is right around the corner).

Old western towns and tales of bandits crowd the gift shops… it’s quite the route of criminal American History.

Roadtripping the Great Lakes Region and the Rust Belt

If you love gritty America, the Great Lake Region and Rust Belt are where to go. No offense to anybody living there, I mean, I live in the rust belt technically (the Hudson Valley of upstate NY), but it’s the most rundown part of america. Old industrial cities left for ruin and abandoned hotels of the Poconos and Catskills in New York and Pennsylvania run rampant. Why is that?

Well, they used to be major vacation spots until airplanes and cars became mainstream and long-distance travel completely decimated its tourism industry, which is what made those towns once beautiful. Now they look like a pile of red bricks from Cleveland to Albany, but I love walking around deserted hotels and mill factories and taking pics.

The architecture of Detroit and Newburgh also add to your photo library quite nicely.

Roadtripping the Midwest

The midwest has some of my favorite cities. Minneapolis, Madison, Chicago, St. Louis, Lincoln and Omaha, Kansas City… So many artful cities with eclectic cultures in the midwest. The sprawling cornfields and tornado-like wind are the two characteristics that stand out the most to me.

Let’s Be Frank

Sometimes these are dubbed the fly-over states by asshole Americans… but on the flip-side, if you really want to under this country, the midwest is where you should go. Walk into any diner and have a conversation about life with the waiter and you’ll quickly learn that things work differently in the midwest. If you want to get to know your people, hop out of the coastal cities and over to the midwest to see the difference in culture.

What’s so pleasant about the midwest are the surprises that you run into along the way. The art scene in Kansas City (MO) and Springfield (MO) totally caught me off guard. The nightlife in Minneapolis was a shock. The liberal vibe in Lincoln was surprising, the hills of Cincinnati was pleasant…

Anyway, there’s a ton to learn about what you don’t know if you’ve never really driven around the midwest and stopped off in their cities to dine and dance. Talk to the people while there; make friends and ask questions.

Roadtripping Down South

Road trips are very popular down south, probably because the weather always permits a quickie road trip as does the southwest, so in that respect they are similar. The one characteristic that the south has that no other region can compete with is cuisine. Good food everywhere. Music is right there with the cooking. Nashville, Atlanta, Memphis, New Orleans–tasty bbq and cajun cuisine, and music in the air on every corner.

There are so many different historical landmarks all over and so much history that happened in all these great cities that were once (and some still are) riddled with racism and other suppressive institutions, which we (used) to call history. But the to truly understand the magnitude of how that history still remains relevant today, you have to go down there and speak to the people of the south.

Southerners are polite like no other people are in the country. They are always so welcoming no matter how shitty of a mood you’re in. Whenever I’m down there it’s like I can’t even be irritated for a moment because there’s such gratitude in the air. And that cooking… and that music…

Roadtripping the Northeast

If it’s Autumn, think no further. You need to be in the Northeast. From Pennsylvania and upstate NY to Connecticut and Massachusetts to Rhode Island and New Hampshire to Vermont and Maine, there’s nothing like seeing the trees on fire with reds and oranges in the Fall.

Fishing towns, beautiful beaches, hippie culture, thick-wooded drives with great lobster rolls alongside artsy farms with free dairy barns (take some milk and eggs, leave a dollar) are what make this area unique.

So many little towns to stop off at and they’re all so close together, so you really don’t find yourself driving for very long before stopping off at another destination.

If you come up this way, feel free to give me a ring and we’ll grab a cup of coffee!


You either think astrology is bullshit or use it to guide your life, and this section is for the latter. If you’re not an astrology type of person (like me) then skip down to another section.

Don’t feel like reading all these right now? You can download this post as a PDF.


You’re progressive, original, and independent. Sometimes you can get lost in your need to promote humanitarian causes, even if it seems like it’s taking over your life, and what I mean by that is you’re totally unwilling to compromise about what you believe in. Those are admirable traits and perfect for many types of adventures.

So, I’ve put together some road trip maps that’ll help propel you in the right direction.

  • The Southwest Road Trip
  • The National Park Road Trip
  • The Music Festival Road Trip
  • The Ghost Town Road Trip


You’re compassionate and artistic and music has a major influence in your life. Pisces can often be hopeless romantics, which is perfect for the vagabond road-tripper because there’re so many places to find irresistible and unconventional romance. I’ve fallen in love ten times in one trip before, and it’s fantastic.

So, with that being said, I’ve got just the right routes to fulfill your spirited soul.

  • The Hostel Hopping Road Trip
  • The Cuisine Road Trip


You’re courageous, confident, and optimistic. You like a good challenge and taking on leadership goals. I have a feeling you’re always looking for speed and competition, and so I thought what better competitor for you than the open road? That’s why I’ve put together some challenging routes for you to accomplish, and if you can do it, please report back with evidence.

  • The National Park Road Trip
  • The Big Kahuna Road Trip
  • The Interstate Road Trips (any of them will do)
  • The Adventurers Road Trip


You’re reliable, patient, and practical. Music, cooking, and gardening might be attractive to your type of personality, or maybe some other form of working with your hands. In general, you’re probably pretty artful, which is why I put together the perfect road trip maps for all you Tauri (no, not a real word) out there.

These routes form perfectly to fit your personality.

  • The Cool Small Town Road Trip
  • The Down South Road Trip
  • The Cuisine Road Trip
  • The Big City Road Trip


You’re gentle, affectionate, and curious. The ability to learn new things quickly and efficiently, as well as share your ideas with the world is simply the type of person you are. Sometimes you might be indecisive, which can plague Geminis with decision paralysis. That’s why I think it’s important for you to commit one of these wild adventures. They are all closely-knit routes (as opposed to immensely spread out) and jam-packed with variety to keep you from getting bored–if that’s even possible when on the road! Pick your map wisely and commit, commit, commit!

  • The West Coast Road Trip
  • The National Park Road Trip


You’re tenacious and highly imaginative, but you’re also very emotional and maybe at times overly sympathetic (at the cost of your well-being). You might be a bit of a homebody and prefer hobbies and creative endeavors that can be done in the comfort of your home, like small dinner gatherings with friends, cooking, or gardening. Taking all that into account, here are the best road trips that will give you the adventure you need.

  • The Friends Road Trip
  • The National Park Road Trip
  • The Cuisine Road Trip


You’re creative and passionate and probably have a good sense of humor. People generally enjoy being around your cheerful spirit. The activities you enjoy may be eccentric or energy-driven, like theatre of any sort, concerts, or social gatherings like parties and big dinners. Bright colors and shiny things might capture your attention often. So, with all that being said, I’ve got the perfect road trip routes for you.

  • The Hostel Road Trip
  • The Pub Crawl Road Trip
  • The Music Festival Road Trip


You’re loyal and hardworking. My guess is you’re quite rational, analytical, and like to keep your belongings in order. This might lead to being overly critical of yourself and others, working too hard, or maybe worrying a bit too much. It might be that you have an affinity towards animals, healthy foods, or reading books. If any of these nail the truth, then I’ve put together some routes that should really vibe with your personality.

  • Bang For Buck Trip
  • The Quickie (any one of them will do)
  • The Interstate Ride (any one of them will do)


I’m a libra so I’m partial to this one. I know the reason I take road trips are to balance out my life with nature and business and give me stories to write about. I like to be on the road no matter where I am and honestly have no preference for where I go. As a Libra, I’m very curious and that can often lead to indecisiveness. I’m quite cooperative, which makes road-tripping with others easy or staying at hostels enjoyable. I like to get out of my head at times, and at other times spend my hours pondering the best way to steer my life, and the road is the best place I’ve found to do that. So, here are the best road trips for Libras.

  • The Hostel Road Trip
  • The Roadside Attraction Road Trip
  • Cool Small Towns
  • The Greg and Heather Road Trip


You’re passionate and resourceful. If you have little to work with you somehow make it work, but you also love being right and cling onto truth and facts even if it interferes with family or friendships. With that being said, long-term friendships are one of the gifts of life that you value above all else, and you prove that with your immense loyalty and friendship you offer others. So, I’ve created a few routes that work well with your sign.

  • The History Road Trip
  • The Pub Crawl (if you drink)
  • The Big City Road Trip


You’ve got a great sense of humor and can be quite idealistic at times. This may cause you to overpromise–not because you’re lying, but possibly because you truly believe it’s doable. You love freedom and travel, philosophy and the outdoors. The road is actually your best friend, whether you know it or not. With that being said, here are some routes that will really go well with your general perspectives.

  • The National Park Road Trip
  • The Big Kahuna
  • Cool Small Towns
  • Big Cities


You’re responsible and disciplined where others aren’t. You exhibit great self-control and might be proficient managers. This may give you an air of humility and cause you to highly value family, tradition, and details like quality craftsmanship. Sometimes you love something, and other times you might hate it. A love-hate relationship with many things in life may not be foreign to you. With that being said, here are some great trips that you may resonate with quite well.

  • The Roadside Attraction Road Trip
  • Tunnels and Bridges
  • Old Hotels of America


I’m obsessed with personality types, and not just Myers-Briggs, but the Big 5, the HEXACO test… I love them all. I can’t stop taking these damn tests and try to out-think them all, but generally always end up with the same results. For the Myers-Briggs Personality Test (MBPT), I usually end up as either an INFP or ENFP, since I border extrovert and introvert (unless I take the Big 5–in which case I’m an extreme extravert, or the HEXACO, in which case I’m a bit of an introvert).

Anyway, even though these tests vary and are very difficult to take objectively at times, I thought it might be fun to create a road trip planner exercise to plan a road trip based on your MBPT personality type. These are all just for fun, but it’s kinda like getting a fortune cookie for a great road trip based on who you are.

INFP – The Idealist

According to Personality Perfect, Idealists love analyzing signs and find metaphors to relate symbols to the deeper meaning of life. They are lost in their imagination and daydreams (guilty), and are always drowned in the depth of their thoughts, fantasies, and ideas. So what type of road trip would make for great experience for INFPs?

  • The National Park Road Trip
  • The Southwest Road Trip
  • The Pacific Northwest Road Trip
  • The West Coast Road Trip

Don’t break your routines just because you’re on the road.

If you meditate in the mornings, bring your yoga mat and be prepared to look silly in front of morning shoppers at Walmart. Also take your alone time if you’re with someone. Get up early and drink some coffee at the coffee bar at Dennys before your partner wakes up and do your journaling exercise or whatever it is you do in the mornings. Keep your systems in place.

ENFP – The Champion

Well, I’m an ENFP and according to Myers-Briggs, I (and other ENFPs) like to create my own methods, looks, actions, habits, and ideas. ENFPs hate cookie-cutter people and never want to live inside a box. ENFPs are highly reactive towards feelings and extremely thoughtful. So, after some careful consideration, this one was quite easy. I simply put together my favorite road trips and I’ll assume anyone like me will also enjoy them.

  • The Cool Small Town Road Trip
  • The Roadside Attraction Road Trip
  • The Hostel- Hopping Road Trip
  • The National Park Road Trip
  • The West Coast Road Trip

If you’re traveling with someone, let them be the DJ.

Small price to pay for a happy passenger. A happy passenger is a happy driver. Just focus on keeping your road trip partner happy. One of the best ways to do that is to let them control the music or podcasts. Pay attention to when the people you’re with need some alone time. Be wary of this as you make friends or travel with family.

INTJ – The Mastermind

You’re quiet and reserved and comfortable being alone. Most likely you’re self-sufficient and prefer working alone. Sometimes socializing can drain your energy. You might be very intrigued by ideas and theories and might always question why things operate the way they do. Here are some road trips that you might find inspiring:

  • The Yellowstone Road Trip
  • The Cave Road Trip
  • The Big City Road Trip – East Coast

Never debate in the car.

Debating in the car is like a pillow fight in a closet… you’ll suffocate pretty quickly. You’re going to find so much inspo (did you know that word was just added to the dictionary?) and have so many ideas to share that you might get too heavy. Keep it light!

INTP – The Thinker

INTPs are usually incredibly logical, love patterns, and can easily see when something is awry. You’re constantly looking for the perfect environment to allow your creative genius to thrive. so, with all that being said, there are a few road trips that I think work well for your personality type.

  • The Bang for Buck Road Trip
  • The Small Distance Road Trip
  • The Interstate Road Trips (any of them are good choices)

Choose by season.

If you’re gonna take one of the Interstate Road Trips to get a good lay of the land, choose by season. For instance, if it’s winter, take the I-10 trip or maybe I-40 trip, or if it’s spring or fall take the I-95, PCH, I-5, or I-70 road trips. And if it’s summer, take the I-94, I-90, or I-80 road trips.

Keep it light when you’re traveling with a partner and take some time to process what you’ve just seen before heading off to the next stop-off

ENFJ – The Giver

You can connect with absolutely anyone no matter the difference of background. There’s nobody more extraverted than The Givers. That’s why you’re so charismatic and are able to connect with your fellow people effortlessly. Sometimes you can future trip about all the many ways your life might end up if you don’t do certain things. Maybe it comes in the form of indecisiveness or procrastination. For all these reasons, you’ve got some great options as far as which trips suit your soul the best.

  • The Hostel Hopping Road Trip
  • The Sexcapades Road Trip
  • The Highway Road Trip
  • The Diner Road Trip

Focus on being present.

If you find your mind wandering too much look at the trees and bring yourself back to whatever is in front of you. Oh, and just go the speed limit, it’s simply not worth it to shave off twenty minutes by going fifteen over the limit…

ESFP – The Performer

You love the spotlight; to entertain people and be the center of attention. You’re a born performer. You’re a thoughtful explorer and love to share your findings with others. Any of these road trips would suit you well:

  • The Hostel Hopping Road Trip
  • The Instagram Road Trip
  • The Group Road Trip
  • The West Coast Road Trip

One of the tips I think all ESFPs should follow is this: make sure you don’t spend too much time documenting your trip. Also, whenever you see something that interests you, make sure you investigate it. If you’re driving a hundred miles an hour and pass a sign that piques your curiosity, get off at the next exit, turn around and go back! Don’t keep driving and pass it by

ENTJ – The Commander

Did you know that you’re most likely to make the most money out of all the other fifteen Myers-Briggs personality types? Yup. It used to drive me crazy because I was likely to make the least amount of money and I was dating a girl from Minneapolis that was an ENTJ and clearly making Commander moves… So, relish in that. That’s you. You’re a natural leader and the people need you. I think all great leaders need to see the whole country and understand many different cultures of the land. That’s why I’ve suggested these road trips below, because I know it’ll build your character while also giving you the opportunity to see the entire country.

  • The Big Kahuna Road Trip
  • The Multi-Regional Road Trip
  • The Greg and Heather Road Trip

All of these road trips take you on a tour of the entire country, and if you’re feeling like you want a challenge, which I know you are, you can try to top my Guinness World Record road trip… I’ve even provided the route. Good luck.

ISTP – The Craftsman (or Craftswoman)

You’re logical and rational, sure, but then there are those times you surprise the world with irrational spontaneity–the best kind. You can come outta nowhere with wild ideas and extreme passions, and that’s what makes you so interesting; nobody knows what you’ll do next! Even the people that are close to you. It’s in your nature to be unpredictable, but you don’t show it all the time. That’s why the road is such a great fit for your personality. When you get on the road you can be anyone you want, and the more you choose to be anyone you want, the more you become exactly who you’re meant to be.

This is your time to be wild.

So, with all that being said, I think there are some great road trips that’ll help you uncover your dark side and turn it bright. I think the way to do that is for you to get out and see the part of the country that you know nothing about. Choose any of the following maps–so long as you know nothing about the region.

  • The West Coast Road Trip
  • The Pacific Northwest Road Trip
  • The Mountain Time Zone Road Trip
  • The Great Plains Road Trip
  • The Rust Belt Road Trip
  • The Southwest Road Trip
  • The New England Road Trip
  • The Down South Road Trip

Now that’s a lot to choose from, but remember, the goal is to go where you’ve never been before. Go wherever the exact opposite of your life is. If you’re born and bred in Texas, head over to Brooklyn, or if you’re from Boston, try Jackson Mississippi… The point is: be bad.

ESFJ – The Provider

You’re a social bluejay. I’m tired of the term social butterfly, so today you get to be a bird… but that’s generally where you fall. Basically, ESFJs are the stereotypical extroverts on the spectrum, which means there’s so much to gain from the road. There’s solitude mixed with pleasure… Like taking a dip in the Ouray, Colorado hot springs then spending the night at a smokey den hostel where you can meet all the other vagabonds chasing their wanderlusts. Maybe you’ll even organize a pub crawl, ask the Irish girl to hop in your ride with you till LA then leave your car parked in San Diego to take a quick detour to Hawaii with some Australian you met in Seattle.

The road is your playground.

You need to be around people but also somewhere that’ll give you some nature to reflect on your next big move. That’s why I’ve got these suggestions for your next trip:

  • The Southwest Road Trip
  • The Hostel Hopping Road Trip – West Coast
  • The Pacific Northwest Road Trip
  • The Music Festival Road Trip
  • The Pub Crawl Road Trip

Of course, these are only suggestions. Feel free to peruse the road trip map (there are 100 routes) and pick anywhere that’ll rev you up. You can choose by astrological sign, or mood, or theme, or adventure–whatever you want. But I think these will suit you just fine in case you get overwhelmed with choices.

ESTJ – The Supervisor

Some may say you’re organized and traditional; others may say you’re moral and honest. Above all you believe in what is right and what is good. You don’t fall into peer pressure as you are firm in your faith–not necessarily religious faith, simply faith in what you’re doing. For this reason people turn to you for advice and ask what is the best thing to be done. These personality traits make for a great leader and like all leaders, it’s important to understand the people they lead. That’s why I think the lay of the land road trips might serve you best, so you can see as many cultures as possible and see how people are living from Brownsville, Texas to Bemidji, Minnesota. Here are some routes that may suit your soul.

  • The Big Kahuna Road Trip
  • The Interstate Road Road Trip (any of them are good choices)
  • The Highway Road Trip

All these trips give you the ability to go from one extreme to the next.

Now you can experience the entirety of the country without compromising your organizational nature. One bit of advice to all ESTJs is to keep the counsel to a minimum when in the car with someone else. If you’re solo, you’re gold. If with someone else, make sure to keep it light while driving!

ISFJ – The Nurturer

You’re a humanitarian and philanthropist, always searching for a way to make it better for your fellow humans and animals around you. You might be the most selfless of all the personality types, and given your warmness and kindness to others, you may be the friendliest. Since sensitivity runs in your blood, what better of a place to be than around nature and smaller communities that try their best to live in harmony? That’s why I’ve chosen these trips for your kinda people.

  • The Cool Small Town Road Trip
  • The National Park Road Trip West
  • The River Road Trip
  • The National Park Road Trip East
  • The Pacific Coast Road Trip
  • The National Forest Road Trip
  • The Atlantic Coast Road Trip

Keep a bit of skepticism in your back pocket when you’re on the road.

Just for protection… I once had someone with a junkie-ass car ask my then-girlfriend, Heather, to give him a jumpstart. Given her ISFJ persona, she said sure! But here’s the thing… jumping that car coulda ruined my battery! And I was pissed about it! But we jumped it anyway and then argued for a bit of miles… The point is: don’t do everything for everyone when you’re on the road. Grow a tiny mean-bone and I promise you’ll only have to use it sometimes.

ISFP – The Composer

You love to explore and experience new adventures and you can be spontaneous at times. Most people would never think you’re an introvert, but you are. You gain a majority of your energy from alone time even though you love to socialize. That’s because you find the best way to learn about life and yourself is through other people.. For that reason I think it’s important you enjoy a healthy mix of introvert and extrovert activities. Here are some trips that have that balance you need.

  • Extreme Adventure Road Trip
  • Mild Adventure Road Trip
  • Camping Road Trip
  • Cuisine Road Trip

All these trips allow you to meet people during the day and exert yourself as an extrovert when the sun is up, but allows you to reflect and process the people you’ve met throughout your trip at night and be alone with the open road. People might be offended by your practice of retreating to yourself after a full day of socializing, but that’s okay. They will get over it and realize that’s just the way you operate. You don’t need to explain yourself to anyone.

ISTJ – The Inspector

Some people find you intimidating at first because of blips of seriousness. You’re hardworking and patient, two qualities most people don’t have. This might catch people off-guard at times given your ability to handle social and cultural responsibility. You may also be calm and reserved, which makes it difficult for people to gauge what you’re thinking–maybe that’s why you come off as intimidating at times. In general, you’re often misunderstood. So, I think the road would be a great place for people to see the real you, and the adventurous you. That’s why the trips I picked for ISTJs are as follows.

  • The Instagram Road Trip
  • The Adventurer’s Road Trip (mild or extreme depending on your preference)
  • The Diner Road Trip

These road trips all play into your introvert nature but give you a chance to show a side of you most don’t always see. You can be whoever you want on the road, so, my question to you is this: if you could play the best game of pretend, what would that game look like? That’s the trip you want to resemble because it’ll be a life-changing adventure.

ESTP – The Doer

You’re a true entrepreneur… fixing the mistakes as you go, keeping busy with new endeavors. I doubt you have any interest in philosophical mumbo jumbo or playing it safe and are more concerned with going for the big picture and not slowing down till you get there. If I’m wrong, well… blame it on the personality test–or just go with it anyway! Maybe it’s a sign. Look, you need to get shit done and that’s why I think you need a goal-oriented road trip. So, here are a few goal-oriented road trips that might tickle your pickle.

  • The National Park Road Trip
  • The Collectors Road Trip
  • The Big Kahuna Road Trip
  • The Instagram Road Trip

All of these trips have one specific goal in mind.

For instance, to visit every national park on the west coast, or to collect a rock from every national forest, or to see all 48 of the lower states, or maybe to take the most photogenic road trip possible. But if you’re not into any of them, try choosing from the other maps and see which one stops you in your scroll and makes you giddy… cause that’s the one to take.

INFJ – The Counselor

You’re one of the most creative thinkers of all the personality types and have grandiose visions that others might not be capable of dreaming up. You have a profound way of viewing the world and a depth in the way you think that keeps you from accepting that things must be the way they currently are. Sometimes people may find you confusing because of your different outlook on life, but that’s just you. For that reason, giving you time to really craft your ideas into a vision will be helpful, so I’ve planned these trips for you to choose from.

  • The Big City Road Trip
  • The Cool Small Town Road Trip
  • The Route 66 Road Trip
  • The Interstate Road Trip (any of them will suffice)

Keep it basic when you’re interacting with others on the road.

Don’t unleash your full vision of why things are the way they are and how you can change them; keep those theories to yourself until you’ve gotten to know the basics. Talk about things everyone can relate to, like family, heartache, accomplishments, and adolescence. Even work will do for now, just be basic for a tiny bit of your life. It’s good practice in making small convo.

ENTP – the Visionary

You are one of the rarest personality types out there, did ya know that? Well, here’s what we know about ENTPs: You’re an extrovert but don’t like small talk and actually, you might not even like many social settings, especially if you’re not with your tribe. You need constant mental stimulation and like a good challenge every now and then. Your ability to breakdown comprehensive theories and facts into tiny details may frighten the average socialite, but that’s your cup of tea. So, with that being said, given your need for mental stimulation, I thought of the perfect routes for you.

  • The Scavenger Hunt Road Trip
  • The Collectors Road Trip
  • The American History Road Trip

Now you can really dig your teeth into a project and be on the road at the same time. Make it meaningful and share your findings with the world. We’re all waiting for you to discover the meaning of life, so have at it and give us a shoutout when you’re done.


Want to hear how other vagabonds travel the world? Good news, I’ve got the perfect Travel Podcast for you to add to your already-too-many podcast subscription database…


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