HOW TO START PLANNING YOUR ROAD TRIP

Nobody ever talks about Road trips as being the best therapy in the world, but they are. Nothing can get you out of a rut like hopping in the car and driving somewhere unknown. I’ve been doing it my whole life and now hold the Guinness World Record for Longest Journey by Car in a Single Country. During that Trip, I drove nearly every Interstate and highway in America, going through hundreds of small towns and cool cities all over the country. So, I’ve done my best to make this the ultimate Road Trip planner for your next trip. We’ll go through this in many different ways… so, let’s get started.

WHICH ROUTE IS BEST FOR YOU?

Every route shows you a different place. The saying, “wherever you go, there you are,” doesn’t always apply to me, because in my experience, location has a major influence on how I feel. I don’t want to head to the Loneliest Highway in America (Highway 50, as it’s nicknamed) if I’m feeling disconnected… but I might want to head to Lake Tahoe or wander around Seattle talking to locals. There’s a reason you want to take a road trip right now, so… what is it? That will dictate which direction to drive, where you stop off, and how long of a trip you take. 

That is the goal of this post: To help you plan your road trip based around why you’re taking it to begin with.

I came to one very real conclusion: How you feel right now, and what you want from your road trip is the best way to plan your route, because there’s a trip for every personality type and every mood you’re in; we 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… The type of person you are determines what trip might rattle your soul the most. Your inner psyche is actually the best road trip planner in the world, and I’m going to walk you through how to use that psyche to plan the trip of your needs.

If you don’t won’t to read this post online, GOOD NEWS! I’ve formatted it for you in a pleasant e-book.

PLAN YOUR ROAD TRIP BY ASTROLOGICAL SIGN

Think astrology is bullshit? Well, it might be. But my last roommate in LA was a professional astrologer at one point–now model and actress (yeah, I know… this is off to a bad start). But I just want you to know, I swear I call bullshit on so many bullshit things, but this chick, my ex-roommate and now very close friend, she fucking swears by it… So, I’ve included it as a compass that you may wanna use, or chuck in the trash. Either way, you got the table of contents above so you can skip all over this post and find the best chunk that suits your inner thirst.

Aquarius

Apparently you’ve got a humanitarian spirit, which is why I think one of the many Southwestern Trips I’ve mapped out in my Road Trip PDF would be best for you, and I’ll tell you why: The Southwest is riddled with controversy–cowboys vs Native Americans to name just one–but it’s also the most arid section of the country and most populated with natural beauty. So, you can quench your thirst for nature and be kind along the way by paying respects to all the local businesses that keep the communities afloat.

Pisces (fantasy)

In your head about how the world should be? Well, I’ve got just the place for you. It’s in the Fantasy Road Trip map section, and it ranges from Montana’s Glacier National Park down to Big Bend National Park in southern Texas. You’ll feel like you’re in make-believe land going from Glacier to Big Bend. It’s the most diverse of all the maps.

Aries (challenging)

National Park camping trip

Taurus (relaxing)

Try the Northwestern routes or the Southwestern routes, depending on if you enjoy greenery or desert more.

Gemini (tries to do too many things)

Since you have a fear of missing out, you should just do the entire country with one of my full trip routes.

Cancer (intuitive, adjustable)

Since you can exist equally in many settings, I suggest one of the West to East routes, or North to South routes. You’ll go through many types of weather, geography, and cultures.

Leo (loves the spotlight)

Since you’re so theatrical and passionate, why don’t you try out of the many themed routes and carve your own path? Make sure you pick a theme before you leave or you’ll drive too far and miss your exit.

Virgo (practical)

Since you rely on logic, how about the most cost effective route you can take. Take a look at the Most Bang for your Buck trips I’ve put together for you.

Libra (need for balance)

Don’t want too much of one thing? Try out one of the Culture to Culture road trips I’ve planned out for you.

Scorpio (full of passion and power)

Vivacious are ya? Pick a couple Themed Trips and combine them into the fiery beast of route that you want.

Sagittarius (quest for knowledge)

Want to make a pilgrimage? Well, how about you pick a Boom Blast trip. That way you can enjoy a beautiful route and accomplish a major challenge at the end for spiritual growth.

Capricorn (well-adjusted):

Not thrown off easily? Try an East Coast trip. You’ll get the deep and dark history of the South, not to mention the humid weather, and the no-bullshit, straight-to-the-point personalities of the Northeast all in one.

PLAN YOUR ROAD TRIP BY MYERS-BRIGGS PERSONALITY TYPE

I’m obsessed with personality types, and not just Myers-Briggs, but the Big 5 also. I can’t stop taking these damn tests. I try to out-think them, but I generally always end up as either an INFP or ENFP, since I border extrovert and introvert. Anyway, I thought it might be fun to create a road trip planner exercise to plan a road trip based on your personality type, and this is just for fun, but it’s kinda like getting a fortune cookie for a great road trip based on who you are… So, fuck it. Let’s do this.

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?

I’m going to say that INFPs should gear towards the Southwest, because it’s so vast and whimsically real. A trip up the Pacific Coast Highway (PCH) from San Diego to Canada would also suit the dreamers as well. There’s just so much magic on the Pacific Coastal line and deep in the red rocks of the Southwest that places like Joshua Tree and Death Valley seem to be great starting points… but those are only a couple National Parks that everyone knows about. Try stopping off at Pioneertown CA, Jerome AZ, Flagstaff, Prescott, Sedona, Lake Powell and all the other awesome southwestern towns.

You can download Southwest and West Coast road trip maps here.

ENFP

INTJ

INTP

ENTJ

ENTP

ISTJ

ISNP

ISTP

BEST ROAD TRIPS IN THE USA

If you want to go all out and model my Guinness World Record route (don’t even think about breaking it–just kidding, have at it), you can download the full map above and fold it up to keep in your car because electronic maps just won’t cut it on the road. You need some real-deal maps, the ones you can hold in your hands and fold in seven million directions and shove between your seat and center console (that’s prime real estate when you’re on the road). A good map, atlas, and a travel notebook are the only key ingredients needed for a successful trip, so… now you’re one-third the way there.

STEP 1: DEFINING YOUR WHY

Getting in your car without a clue of where you’re going and driving somewhere is easy; I’ve done it a million times. But it can leave you feeling a bit empty when you scramble to find a motel in the middle of Utah at 7PM without a clue of why you are where you are. We don’t want to drift aimlessly, we want to wander with purpose. So, let’s start out on the right pedal here… Why are you doing this? Whether you’re with friends or solo, here are some reasons you might want to hop in your car right now.

• Family outing
• Going through a breakup/ divorce
• Graduating school
• Losing a job
• Save money on transportation
• Friends adventure
• Quarter-life/ midlife crisis
• Romantic adventure
• Testing out #vanlife
• Thirst for adventure
• Unhappy with life
• Lonely
• Creative inspiration
• Vacation
• Experience the unknown
• Personal growth

This list can go on forever, but it’s very important you know why you are traveling before you plan your trip. Driving to the middle of some southwestern desert or hiking to a lonely waterfall might not be the best place for you if you’re feeling shitty about yourself after a breakup or whatnot. In the same fashion, a trendy hostel in Brooklyn might not be the best fit if you’re looking to get some writing done. So, clarify your why then move onto step two.

STEP 2: WHAT IS YOUR ROAD TRIP GOAL?

What do you hope to achieve from this trip? Certainly you don’t just want to put miles on your car and spend money on gas. Writing exercises are always the best way to prepare for a trip. A lot of the time I like to use worksheets and prompts to help me get started, so here are some sample goals that might resonate with you to help get your juices flowing. Pick one and write a few pages about why you chose that goal.

• Get more out of life
• Get from point A to point B (or maybe point Z)
• Bond with girlfriend/ boyfriend/ wife/ husband/ son/ daughter
• Build confidence
• Make friends
• Find romance
• “Figure out life” AKA reflect
• Enjoy some peace and quiet
• Simply see the country
• Test out living on the road
• Experience new culture
• Write a book
• Take cool photos
• Come back with a story to tell
• Connect with nature
• Rejuvenate yourself
• Find a new place to live
• Finish a great audiobook

Once you know why you’re taking a road trip and what you hope to gain from it, you can decide the best place for you to travel.

STEP 3: PICKING YOUR ROAD TRIP ROUTE

Okay so what are we doing here? Do you want to shed your apartment, put your shit in storage, and head out on the open road with no intent on coming back any time soon? Or do you want to do a ten-day trip and make the most of your time? Either way, let’s break down the country into all the different sections and go over what each region of the USA has to offer. Here are the main regions of the country:

• The Southwest
• The Pacific Northwest
• The Mountain Time Zone
• The West Coast
• The Great Plains
• The Great Lakes and Rust Belt Trip
• The Midwest
• The Northeast
• The South
• The East Coast
• New England

Another way to decide on which road trip might be best for you is to pick a road trip theme:

• Roadside attractions
• National parks
• Tent camping
• Hiking
• National monuments

Let’s break down what each region of the USA has to offer.

1. The weather
2. Lodging (car-camping or hostel hopping or hotel crashing)?
3. The experience you want

You might want to start by considering when you’ll be traveling, which would mean starting with the weather. If you’re wide open and can travel whenever you want, start with the experience you want. For most people, I think the window of time available for travel is stringent, so I’ll start with the time of year, which will denote the type of weather you can expect, and the type of weather you can expect should influence where you travel and the route you take.

THE WEATHER

If you’re gonna be sleeping in your car–or “car camping” to make it less trashy sounding, you gotta take the weather into consideration. 70 degrees may sound nice and breezy, but in that Houston humidity, you’re not gonna sleep very well. However, 70 degrees feel quite different if you’re in Missoula, Montana… where 70 degrees is perfect outdoor sleeping weather.

If you’re going to be driving during the winter, you drive through the Midwest, but you better have all-wheel drive and be prepared for Minnesota’s black ice at night.

You might wanna stick to the I-10 route for a warmer drive.

WHAT DO THE INTERSTATES NUMBERS MEANS?

ANSWER: Interstates ending in odd numbers run North and South. Interstates ending in even numbers run West to East. Rumor has it that West to East Interstates denote the amount of land south of the highway. For instance, below I-94 is 94% of the USA. Below I-10 is 10% of the USA. Same goes with North to South Interstates. To the west of I-95 is 95% of the country. The exception is for the three-digit Interstates. Three-digit Interstates are related to a two-digit Interstate. For instance, I-495 is related to I-95. The even number in front of it means it will run into another Interstate or go in a loop. Three-digit Interstates starting with an odd number usually mean they end in a city… But here is a much better post about the meaning of Interstate numbers. Back to why the weather is so important…

If you’re on the West Coast, the weather is always perfect, in winter or summer, but is best during the Spring, so you’re better off saving this route for April or May. Down south you’ve got only a few windows to take advantage of, because it gets cold in the Appalachians during the winter but during the summer it’s far too hot. The best way to do the South is to start in the mountains at the end of summer and make your way to the flat land of Mississippi and Louisiana closer to Autumn, or vice versa and start on the flat lands during the end of winter and make your way to the mountains as the weather gets warmer.

LODGING

If you’re sleeping in hotels it doesn’t quite matter, but you’ll want to add some camping in the mix, right? In any case, let’s begin by breaking down all of the routes that you can take. We’ll start with regional road trips to see which region best suits your goals and experiences that you want to have. If you’re intent on traveling the whole country, you can skip down to that section here.

THE EXPERIENCE

REGIONAL ROAD TRIPS

If you don’t want to go from one side of the country to the other and only have an interest in a specific part of the country–maybe you want to see all the national parks or fun roadside attractions or some cool thingy you saw in that movie once… then here are your options:

1. The Southwest Trip
2. The Northwest Trip
3. The Mountain Time Zone Trip
4. The West Coast Trip
5. The Great Plains Trip
6. The Great Lakes and Rust Belt Trip
7. The Northeast Trip
8. The Down South Trip
9. The East Coast Trip

ROAD TRIPPING THE SOUTHWEST

If you like the wide open desert towns and landscapes, the Southwest is where you want to be. This is also where you can squeeze in as many national parks in the least amount of distance. Make sure you get the annual pass so you’re not paying admission to every park you go into. More on that later, but the Southwest is where you’ll see shooting stars in the desert night and find that extreme solitude you might be craving.

There’s a difference between the solitude you find in the Southwest and the solitude you find in the Rocky Mountains. In the mountains you feel like there’re animals and plants and life all over. If you’re in Arizona you won’t feel a breath of life in any direction and the views are so broad that life feels vast and your part in it feels tiny. It’s quite a different feel hiking in the Mohave Desert than it is in Durango. The Southwest has a way of giving you complete solitude. If you want to see rocks the size of dinosaurs every turn, make your way to five national parks in three weeks, drive by canyons dipping into the Earth and old cowboy towns left deserted with few tourists around, then the Southwest is the region for you.

ROAD TRIPPING THE NORTHWEST

If you’re looking for water, go to the Northwest. It’s the only place in America you’ll find massive rivers and giant waterfalls on every turn, even when you’re just trying to find a gas station you’ll always be surrounded by rivers and greenery.

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FUN FACT: What’s the most mountainous state in America? Nevada. #VagabondSecrets
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Even though Nevada is the most mountainous state, you’ll wonder how that could be possible after driving around Washington. It seems like they never end! You’ve national parks and beautiful cities and you can cross over to Canada and check out Vancouver. Though the mountains are really spectacular, you’ll notice in eastern Oregon that it feels like you’ve been transported to somewhere in Indiana with its flat land and real country vibe. Western Idaho is a place you’ll never forget. It’s probably my favorite spot in America. I just love those little towns and beautiful rivers and fun-to-talk-to fishermen. It’s such an amazing place. Anyway, if you’re looking for water and greenery, you’re going to the Northwest.

ROAD TRIPPING THE MOUNTAIN TIME ZONE

If you like small mountain towns and lots of twists and turns, the mountain time zone is where to go. There’s so much to see in so little time! I say so little time because it takes an hour to drive ten miles when you’re driving on roads like the Bear Tooth Mountain Pass (which I believe is not even open during the winter), which is the road that takes you out of Yellowstone National Park in Wyoming and into Montana. Every road from Montana down to New Mexico is riddled with Rocky Mountains, and if you don’t want the Rocky Mountains, you can drive west for a day and get lost in The Sierras. The hard part about the Rockies is if you’re car camping. Some of those roads are so windy you’ll have to drive sometimes a long distance before you arrive at anywhere you can pull off to sleep.

ROAD TRIPPING THE WEST COAST

I lived in Los Angeles for about six years and I can tell you that driving the PCH (Pacific Coast Highway) never gets old. I’ve driven that road 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. You go by some of the most insanely amazing shit. The cities you’ll see are awesome…

You’ll have to get off the road and drive inland for a bit to get to these cities, but assuming you do that, you’ll start in San Diego and hit Los Angeles and then Santa Barbara and Big Sir–probably my favorite place–and San Francisco up through the Napa Valley and Eugene and Portland and Seattle… it’s really a spectacular drive.If you want to feel like you’re driving through vacation town after vacation town and really live that beach life, the west coast is where to be.

FUN FACT: How do you sleep for free on the PCH if since there are no rest areas, truck stops, or Walmarts?
ANSWER: You park by the beach and pay the parking ticket that you’ll get every now and then. It’s the cheapest way to do it!

ROAD TRIPPING THE GREAT PLAINS

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ROAD TRIPPING THE GREAT LAKES AND RUST BELT

If you love gritty America, the great lake regions is where to go. No offense to anybody living there… I mean, I live in the rust belt technically… but it’s the most rundown part of america. Old industrial cities left for ruin and the abandoned hotels in the Poconos of Pennsylvania and the Catskills in New York are everywhere. 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 kept those beautiful town afloat. Now it’s sad to say they looks like a pile of red bricks from Cleveland to Albany, but I love that shit. I find the history so amazingly interesting and walking around deserted hotels and mill factories is creepy, but also fucking awesome. It just depends on what you’re going after. There really is no “best part” of the US… every part has a unique capability to make you feel a certain way. The architecture of Detroit and Newburgh are beautifully destroyed. There’s no place like it.

ROAD TRIPPING THE NORTHEAST

If you want fishing towns and cape cod, you’ll want the northeast. If you love good food and immersive culture, head down south. And then there’s Texas. You can drive for nearly a day straight (I mean 24 hours) and still not be out of the state.

WHICH ROAD TRIP SHOULD I TAKE?

THE NATIONAL PARK ROAD TRIP

Most people want to stop off at a few or all of the parks. That makes total sense, I mean… they’re awesome. Some of the national parks are overplayed (IMO) and some seem to be completely forgotten about in all those “top 10 lists.”

The southwest AKA the wild wild west has the most National Parks in the closest vicinity. When I say southwest I’m referring to eastern California, New Mexico, Arizona, Utah, western Colorado, and West Texas. You can knock out all these parks in a relatively short distance of land:

1. Death Valley (California)
2. Joshua Tree (California)
3. The Grand Canyon (Arizona)
4. Bryce Canyon (Utah)
5. Arches (Utah)
6. Capital Reef (Utah)
7. Canyonlands (Utah)
8. Great Sand Dudes (Colorado)
9. Big Bend, Guadalupe (Texas)
10. Saguaro (Arizona)
11. Carlsbad Caverns (New Mexico)

1. ROAD TRIP HACKS

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