11 Vehicles for a Free and Spontaneous Life


A vehicle is usually the largest product purchase you ever make. Consider these options to optimize your life for adventure.

Some of these choices are unconventional and you’ll be thinking, “Why didn’t I think of that?!”

01 Jeep Gladiator (Coming 2020)

Jeep Gladiator
Jeep is re-entering the popular midsize truck market for the first time in more than two decades.

I owned a Jeep Wrangler for over 10 years. They are the most capable off road vehicles on the market, insanely fun, and girls love to jump in them.

However, a standard Wrangler is an impractical vehicle. The main shortcoming being lack of storage area.

Finally, Jeep is addressing this by introducing the Gladiator – a Jeep with a pickup bed. It is a modern hybrid of two older Jeep vehicles – the CJ-8 Scrambler and the original Gladiator pickup.

The new Jeep Gladiator has all the fun of a wrangler and the versatility of a pickup. Fun, tough, sexy – no compromises.

Financially, Jeeps retain their value better than any other vehicle. It is one of the few vehicles you can buy new and not encounter significant depreciation. Saved money = more freedom.

02 Stealth Camper Van

As I’ve written about previously. RV’s are not suited for young people – primarily because campgrounds are infested with annoying baby boomers.

Enter – STEALTH. It looks like a regular work van on the outside, but it’s like RV on the inside.

Unlike an RV, you can park a “regular van” anywhere! Your friend’s driveway, a parking lot, on the side of the road, in down town LA, anywhere! RV’s and overt camper van’s can’t get away with this because all cities have draconian ordinances against camping. Police aggressively enforce these laws. This is why stealth is so important! Nobody notices the random “work van.”

How to do it right: If I could go back to when I was 24, I would buy an inexpensive house and then rent out all the bedrooms with the provision that I can live in the driveway in my van and use the house for showering/bathroom/kitchen/living room. The renters would pay my mortgage and I can have a cool van. See my post about the “Van-Bedroom” strategy to get ahead in life.

03 The “Beater”

Beater Car
“Freedom is just another word for when you have nothing left to lose.”

If you drive a “beater,” you just might be a winner disguised as a loser.

Priorities: Your car costs $20k less than your peers so you now have the funds to start a business or travel the world for a year. Insurance costs are lower too.

You’ll never care if you car gets a scratch or you have a fender bender. It gets you in the habit of not being addicted to consumerism. This helps you achieve the low stress attitude of an alpha.

Increased Maintenance: This is an upside in disguise. Parts for old cars are cheap at junkyards and you can learn to do repairs from YouTube. This helps develop you into a true, competent man.

04 Earth Cruiser

Earth Cruiser Mountains
The most competent overland vehicle in existence.

Earth Cruisers are the finest engineered overland vehicles in existence.

Obviously, this is a vehicle for men of means. Prices start at $175,000.

Interesting note: The border crossing from Russia to Mongolia is jammed with vehicles like this during the summer. I would have photographed the spectacular scene when I crossed with Igor in 2018, but photography is forbidden at the border.

Mongolia is a land of vast open land and no fences. A perfect place for over-landing.

05 Super Fuel Efficient Vehicle

prius road trip vehicle fuel efficient
Reliance on fuel/money is a constraint – minimize it!

I call this the “road trip enabler.”

The primary inhibition to a spontaneous road trip is fuel costs. Owning a fuel efficient car like a Prius lets you say, “Sure, let’s go!” more often. It also reduces your re-occurring fuel costs in daily life.

Although not exactly a fun or sexy vehicle, I gained more respect for them when I saw them in action in Mongolia. Yes, in Mongolia these are actually the most common vehicles! Mongols drive them across the steppe even when there are no roads. Driver skill counts for a lot.

Prius offroad Mongolia
Alpha Male Prius owner.

06 Live Aboard Sailboat

Live aboard sailboat

This piece of old technology is still peerless in the modern era. It is the only vehicle that can travel thousands of miles for FREE. When not traveling, you can dock in ports for cheaper than renting an apartment.

Once satellite internet speeds get better you could live a fascinating digital nomad life in a sailboat.

Not many people sail anymore and those that do are getting older. Excellent used sailboats can be gotten cheap.

Doing it right: Laura Dekker sailed around the world at age 14! I highly recommend her movie.

  • Laura Dekker
  • English

07 Ural Sidecar Motorcycle

Ural motorcycle babe and dog
Peak Aesthetics

These bad-ass Russian motorcycles are starting to gain a cult following in the U.S. due to their hipster compatible aesthetics.

The sidecar is perfect for carrying gear, dogos, and girls. They are off-road beasts as the sidecar wheel can be engaged with the primary wheel for 2-wheel-drive.

They have a horrible reputation in Russia as most of the ones they have are old and worn out. Ironically, the newly produced ones being imported to America are much more reliable. ‘Murica!

Get a patch to keep the dream alive until you save the money to purchase your own URAL.

These Russian bikes are so interesting to me that I wrote a dedicated post: 6 Reasons you need an Ural.

Doing it Right:

Hubert Ural adventure rider
The legendary Hubert Kriegel. 12 years on an URAL. Absolute LEGEND!

Check out Hubert. He traveled around the world in a URAL for 12 years! Sadly, he passed away in 2018, but his website is still up. Hubert lived gloriously to the end – an inspiration.

You can buy your own URAL here.

08 Pickup with FlipPac Camper

pickup with flip pac camper

Compact pickup trucks like a Toyota Tacomas are already popular vehicles. A FlipPac Camper is the ultimate accessory.

If you want to spend the maximum amount of time camping, you need to have minimal friction to getting out the door. With this setup, you are always packed and ready to go – while maintaining the practicality of a daily driver.

09 Float Plane

float plane alaska dock bicycle

A float plane is the best way to routinely set foot on land that no other human has before. Great expanses of the northern hemisphere are speckled with lakes that are unreachable by road. You can access absolutely virgin wilderness, fishing, and hunting with a float plane.

I’d carry a lightweight dirt bike in the back to scout new areas.

10 Volkswagen Vanagon Syncro

volkswagen vanagon camper motorcycle
Nothing warms my heart like a deployable motorcycle.

The Vanagon Syncro is the 4WD decedent of the iconic “Volkswagen Van.” Unfortunately, they are no longer produced, but they remain the apex of camper van design.

They strike the perfect balance of size, interior space, fuel efficiency and off-road capability. Due to the rear mounted motor, they are deceptively spacious inside. The top pops up for sleeping and the living compartment has a table, couch, refrigerator, and stove.

Imagine just being able to pull over and take a nap.

The Bad: Only imported to the U.S. from 1986-1991, they are getting harder and harder to find. Since there is no modern equivalent, the old ones are in high demand.

11 Bonus Vehicle: Fully Electric Camper Van

route del sol fully electric camper van

A solar powered, electric camper van – consider me interested.

The first prototype of such a vehicle is currently being driven from Alaska to Argentina.

Check out the project at: Route Del Sol.

Any other ideas for the list? Sound off in the comments!


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