How to Start Overlanding

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If you’re wondering “how to start overlanding,” you are probably already following the social media accounts, vlogs and blogs of overland travelers, which is an excellent way to start learning and gaining inspiration. Beyond that, were you to gather 10 overland travelers together and ask each of them how they started overlanding, I can almost guarantee you would receive 10 entirely unique answers. Take for example the stories of the intrepid travelers you’ll find throughout this article.

These stories are included to underscore that there is no “right way” to start overlanding — whether your intended journey is meant to span a week and a few counties or a year and a few continents. But there are a handful of items that need to be considered in each case. Below we’ll provide a few suggestions and things to think about that might make whichever journey you choose to make, or whichever journey that unfolds into being, a little smoother. 

Get Outfitted

Pick your rig and figure out what you need to be comfortable, safe and happy. Remember that less is usually more when you first start overlanding. Building your kit slowly, selectively and by utilizing crowdsourcing to find out which products others with your rig or similar travel plans are happy camping with, can yield a “road home” that is perfectly suited to your needs. 

A winch demonstration by 7P. (Image: 7P Overland)

A winch demonstration by 7P. (Image: 7P Overland)

Get Trained

Most of us learned to drive in our mid-teens. By the time we set off for our overland travels, our skills may be a bit rusty. A defensive driver course or Motorcycle Safety Foundation course to refresh basic skills are highly advisable.


Is it possible to travel around the world on pavement? Probably. But why would you want to drive by some of the most beautiful vistas just because you don’t know how to ride or drive your vehicle off-road? There are a variety of means by which you can receive off-road driver training. The more accessible and affordable options occur in conjunction with events like Overland Expo (shameless plug).

If you’re really serious about improving your off-road capabilities as a driver, 7P Overland and Dragoo Adventure Rider Training (DART), the companies Overland Expo contracts to provide our event training programs, both offer private, multi-day courses which allow participants more in-depth, personalized training experiences. Similar companies can be found in almost any tri-state region in the U.S. Being able to avoid getting in trouble while off-road or knowing how and having the practiced skills to self-rescue (or rescue others) is invaluable. 

Jerry Schmidt – Subaru Forester

Jerry Schmidt began overlanding when all of his belongings (but for his van) were destroyed in a flood. While he was waiting on the insurance payout, he began a project he had always wanted to take on: build out his Subaru Forester to be a go-anywhere, do-anything mobile office/home. With minimal personal belongings to worry about, his Forester build provided a fresh start in a new home on wheels and he’s proud to have visited 18 National Parks to date. 

Yellowstone National Park (Image: My Ticket To Ride)

Yellowstone National Park (Image: My Ticket To Ride)

Test Trip

A test trip is a journey that will take you a fraction of the distance and time that your intended overland trip eventually will. If you’re an avid camper, maybe your test trip is a multi-week journey, where you try out a new refrigerator or a new set of tires.


If you’ve never been camping before and want to see if overlanding might be something you’ll enjoy, visiting a campground in the town next to the one you live in would be a wise place to start. Test trips provide precious journey-, rig- or kit-altering information to the traveler. It’s always easier to change your set-up while you still have a shipping address, a workshop, and a network to utilize.

Tim and Marisa Notier explore Africa (Image: Notier’s Frontiers)

Tim and Marisa Notier explore Africa (Image: Notier’s Frontiers)

Tim & Marisa Notier – KTM 1190

Tim and Marisa of Notiers Frontiers began overlanding by taking shorter trips to gatherings like Overland Expo and Horizons Unlimited. At these events, they were able to learn about other’s experiences overlanding through attending classes and talking with new friends in the campground at night. Before setting off on their (ongoing) multi-year, multi-continent journey, they took a “test trip” around the U.S. The test trip was designed so that Tim and Marisa could make sure that overlanding was something they would both enjoy. What’s more, they were keen to find any adjustments they’d need to make to their setup. Tim and Marisa have now ridden their KTM 1190 two-up more than 42,000 miles through 25 countries.

Your Belongings

Regardless of the projected length of your overland journey, you will have some amount of “stuff” that needs to be dealt with before you can leave. Maybe you just need to arrange for a neighbor to water your plants for a week or two. Maybe you need to consider putting your things in storage, selling your home or renting it out. Whatever that looks like, having a support system in place to help you deal with your “stuff” is good.


For example, if you rent your home, having someone who can check on it and facilitate any necessary repairs is wise. As is having someone you trust who can act as a proxy on your behalf and sign legal documents for you. Like anything having to do with your finances.

Jill Sessa – Sprinter & Honda Trail

When her 40th birthday and Hurricane Sandy hit at the same time, Jill Sessa was living in a fabulous (but expensive) apartment in Brooklyn, New York. Upon realizing that she was working just to pay for her lifestyle, she rented out her swanky apartment, traded up her vintage 150cc for a modern 250cc Vespa, and took off across the country to enjoy meeting new people and soaking up stunning natural landscapes. She realized that she could run her WordPress business from the road. She now does exactly that from her self-built Sprinter conversion that holds a Honda Trail, bicycle, two kayaks and a tiny dog named Logan. ”And the positive energy of dozens of Road Angels who have come to the assistance of this solo traveler,” Sessa added.

Jill Sessa, Logan and the “Flying Tomato” Sprinter (Image: Aaron Ingrao Photography)

Jill Sessa, Logan and the “Flying Tomato” Sprinter (Image: Aaron Ingrao Photography)


Making sure your finances are in order is a must. Budgeting for an overland journey can be daunting, but it doesn’t have to be. Identify overlanders whose blogs you enjoy and talk to them about how they handle their budget. Of course, everyone will be different. In order to successfully plan your costs, you will need to consider how you will be happy living on the road.

Are you perfectly comfortable sleeping in a tent? Or will you need to factor hotel costs into your budget? Do you plan to eat every meal in a restaurant? Or cook between one and three meals per day yourself? 


A personal tip: One of the things that gave me the most peace, in terms of budgeting, was to have a fiscal “exit plan” and worst-case-scenario slush-fund in place. Before you finalize your budget, I recommend considering the following points: 

  1. If you need to return home unexpectedly, are you willing to leave your vehicle behind permanently? Or will you need to have the funds to get it home from any point along the way in your destination? 

  2. If your vehicle fails and requires major repairs, are you willing to ditch it and end your trip prematurely? Fix it? Or replace it?

The dollar signs associated with the answers to all of these questions are very different, and this is one of very few points where I recommend addressing “worst case” types of scenarios in your planning.I have found planning for a worst-case scenario provided confidence in my budgetary planning to start off on a strong foot and carried me throughout my journey.

The bottom line is that you need to be able to land somewhere that makes you happy or return home whole once your overland journey is over — whether whole is with your vehicle or simply with your body and memories intact.

The author “de-palletizing” her motorcycle in Miami, FL after finishing a ride around South America. (Photo: Pedro Andres Sanz)

The author “de-palletizing” her motorcycle in Miami, FL after finishing a ride around South America. (Photo: Pedro Andres Sanz)

Get Inspired

I’m not talking about listening to stories about the most wonderful waterfalls people have seen or the most amazing meals they’ve enjoyed in a far-flung country. I’m talking about reading true travelogues or watching vlogs by travelers who are honest about the hard days. 

SEE MORE: Silver Linings: How the Worst of Times Became the Best of Times

While Instagram accounts of overland travelers can make it appear like a perpetual vacation. I can assure you that is far from the case. You might wake up in the most perfect, secluded, picturesque camp spot one morning and pitch your tent near train tracks next to a camp of homeless people that evening. No joke – I’ve literally “been there.” While many overlanders qualify the experiences they had during their journeys as some of the most meaningful in their lives, it is wise to remember that rainbows require rain. 

Bobby V – Honda Shadow

At 73, Bobby V’s wife was killed in a drunk driving accident. To process his grief, he told his friends he was going to ride his motorcycle from Arizona to the “bottom of Mexico.” When he got to the Guatemalan border, he decided he was enjoying himself so much. So, he didn’t want to turn around. He sent friends postcards highlighting the adventures yielded by his newfound freedom from 11 more countries. I met him at the world’s second largest motorcycle rally in Argentina, where he won the award for “oldest rider” (at 74). Bobby V proudly slept next to this bike with a tarp pulled over him as shelter, while the rally raged on around him that evening. He wore a grin along with his weathered leather vest, and had no plans of stopping his ride in anywhere or anytime soon. 

The author with Bobby V in Apostoles, Argentina. (Image: Roel Bremmers)

The author with Bobby V in Apostoles, Argentina. (Image: Roel Bremmers)

Don’t Over-Plan

Over-plan and you might never leave. Planning for an overland trip, especially if it’s long-term/long-distance one, can be unnerving. So unnerving, in fact, some people never make it past planning.

Having a general idea of where you want to go and what you want to do is important. Knowing basic information about your vehicle is essential.  Know location-specific information like what inoculations will be necessary along your route and what paperwork/fees border crossings will require. These things will go a long way.

Beyond that, make sure your finances are in order, your Plan Bs and Cs are solid, and that you’re very comfortable with the fact that you will probably resort to Plan D more frequently than you ever have in your life. 

Three of the most salient lessons that I learned while traveling overland are:

  1. There is a fine line between necessary preparedness and over-thinking/over-packing (especially on a motorcycle journey).

  2. The knowledge of how to avoid problematic situations or self-rescue made all the difference.

  3. Accepting the kindness and generosity of strangers, when needed, yielded some of my most cherished travel memories. 

Now get out there and go overlanding!

Header image: Azure O’Neil

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Photo by Brett Willhelm


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