ADVENTURE TRAVEL PLANNING 101: THE COMPLETE GUIDE TO TRAVEL PLANNING FOR ANY DESTINATION
Source: Open AI. Created by Dutch Park.
ADVENTURE TRAVEL PLANNING 101: THE COMPLETE GUIDE TO TRAVEL PLANNING FOR ANY DESTINATION
“I don’t know, I’m making this up as I go”
Way back in early 2002, I documented my first plan to embark on my grand adventure in a composition book, which I ambitiously titled “The Great Cambodian Adventure.” Looking back, it was a bit of a bold title. Especially considering my entire international travel experience up to that point consisted of a single trip to Paris and working on an Army base in the Middle East.
The composition book itself was more of a collection of random ideas, places I wanted to see, a few hotels I found in a Lonely Planet guide, snippets of information from phpBB forums, and not much else. By the end of my trip, I had forgotten to do some things I originally planned to, forgot a few things, and had a few mishaps due to my lack of preparation.
These days, YouTube and travel apps have eliminated over 90% of the challenges I faced on that first trip to Cambodia. This is especially true in the developing world or regions once considered "the 3rd world." Today’s tools provide up-to-date information, recommendations, and real-time navigation.
One of the things I always struggled with was remembering to do all the small, often-overlooked details that needed to be accounted for before I set off. The excitement of visiting a new country always makes me focus on the big-ticket items, like booking flights or accommodations, while forgetting the smaller but equally critical things I have to do.
SOME THINGS I HAVE FORGOTTEN TO DO:
Having exact cash for visa fees: Forgetting that turned a $20 visa on arrival into a $100 visa.
Downloading local apps beforehand: This results in me having to buy an overpriced airport coffee just to use their Wi-Fi.
Filling out and submitting visa forms in advance: I didn’t know all visas on arrival in Cambodia are done on an app now.
Researching SIM shops in the airport that don’t rip you off: Paid $5 for a SIM that lasted two days (was supposed to be good for the month).
Not having the local spelling of my hotel’s address on my phone: If you use anglicized spelling, the location won’t always be accurate in ride-share apps, plus a local tuk-tuk driver most likely won’t be able to read it.
PLANNING METHOD FOR A BUSY MIND
The original idea for this adventure planning method came from realizing early on that my mind seemed to work differently from everyone else. I struggled to remember things if I only read them, but if I watched a movie or documentary I could remember everything in vivid detail.
Combined with the constant chaos of my mind, like a blender with 1,000 thoughts swirling at once, getting myself to sit down and plan things out step by step was a battle. I knew I needed to figure out a way to focus my mind to work on one thing at a time, or the rest of my life would be challenging, to say the least.
Eventually, I discovered that using Post-it notes stuck to a wall was the perfect solution. Visual organization helps break down complex tasks into manageable steps, making it easier for me to prioritize and focus. It allowed me to see the big picture at a glance while also tracking individual progress, which is essential for ensuring nothing falls through the cracks in my travel planning. This method helped me identify problems requiring solutions and track my progress by showing what still needed attention and what had been completed.
MAKING YOUR TRIP REAL AND TANGIBLE
For me, there’s also something uniquely effective about the tactile connection of physically planning something and holding it in your hands. It makes my upcoming trip feel tangible and real. Every time I walk past a wall of Post-it notes, I get a surge of encouragement, no matter how far off the departure date might be. Plus, it doubles as a fantastic conversation starter when guests come over. It’s definitely more intriguing than a crooked Warhammer print hanging on the wall.
POST-IT ADVENTURE TRAVEL PLANNING METHOD
THE POST-IT NOTE METHOD:
Grab a stack of Post-it notes and a pen.
Write down the Main Tasks or Problems to Solve, one per Post-it note.
Stick it on a wall.
Break each Main Task into Small Steps:
Write down five or fewer smaller steps or actions it will take to complete the Main Task, each on a separate Post-it note.
Stick the smaller steps underneath each corresponding Main Task.
Repeat this process for every Main Task or Problem until you have a full visual map in front of you.
START TAKING ACTION:
Tackle the smaller steps one at a time.
As you complete each step, draw a line through its Post-it note to track your progress.
Watch your progress unfold:
Keep going until all tasks and problems are completed.
And that’s it—your travel plans are visually mapped out, manageable, and trackable.
WHERE TO GO?
There’s no one-size-fits-all answer for this; it all depends on you and what you want to get out of your adventures around the world. Some might gravitate toward hectic metropolises like Bangkok or Medellín, where the nightlife thrives and there’s always the opportunity to make local “friends.”
FIRST TRIP WONDERS
I’ll never forget my first ride from the airport on Phnom Penh’s roads in the early 2000s, with oceans of tuk-tuks and 150cc motorbikes all snaking through pothole-filled streets, many not even paved and barely a building above six floors. Jordan, on the other hand, was like I had somehow stepped onto the set of Casablanca, with its limestone and concrete buildings stretching as far as the eye can see.
-TYPES OF DESTINATIONS:
CHAOTIC METROPOLISES: Cities like Bangkok, Medellín, and Hong Kong that have wild nightlife and a vibrant dystopian feel.
LESS-DEVELOPED COUNTRYSIDE: Smaller towns off the beaten path in Vietnam or fishing villages in Costa Rica for a step back in time.
RISKIER DESTINATIONS: Countries such as Colombia, Kenya, and Myanmar, along with cities like Johannesburg or Dar es Salaam, can have issues with political instability, a higher rate of petty theft, scams, and occasional armed robberies, with remote areas still having issues with guerrilla groups and bandits.
STRAIGHT-UP DANGEROUS PLACES: Active war zones, countries that are on their fourth president in as many years, anywhere with a ‘secret police,’ and a lot of missing person flyers on telephone poles. And any city where the locals say, “The police are not allowed to go into (the favelas, that province, that neighborhood—you see where I’m going here) because the (gangs, militia, rebels, guerrillas, pirates) won’t let them enter.”
MIXED DESTINATIONS: Regions like Eastern Europe or countries such as China that combine developing world charm, modern conveniences, and a hint of risk.
When I first started traveling, I was a mixture between a Chaotic Metropolises guy—because I was young and single and liked to party—and a Riskier Destinations guy because I watched way too many movies when I was a kid. To this day, I still love big cities in the developing world or old-school cities like Hong Kong. To me, they are just as energetic and unpredictable as any jungle, with the added vibe of my favorite dystopian movies. I later graduated to straight-up dangerous places, having spent time in war zones and gang-controlled towns in Latin America.
OLD MAN ADVENTURE TRAVEL
Now I am getting a bit long in the tooth for hitting the clubs, so I don’t party like I used to—or party much at all. These days, I find beach towns in Southeast Asia the perfect fit for me. Places like Boracay in the Philippines or Da Nang in Vietnam offer a slower pace with cheap, fresh seafood, and all the amenities of a Western city, all wrapped in a developing country vibe.
MY STORY: HOW I CHOSE A COUNTRY FOR MY FIRST ADVENTURER
For my first adventure trip way back in the day, I was influenced by my childhood and growing up in a small, boring town where the most exciting trip anyone around me ever took was a bus tour through Europe. My window into the world was my VCR and a Zenith 32” TV (yes, I’m that old). I spent hours watching movies like Salvador, Saint Jack, Romancing the Stone, Raiders of the Lost Ark, and The Year of Living Dangerously. But the movie that left the deepest impression on me was The Killing Fields.
WAIT, THIS IS REAL?
Until I saw that film as a kid, I had never even heard of Cambodia. I was captivated by the story of the Khmer Rouge taking over the country in a brutal civil war, as told through the eyes of an American journalist, and the aftermath, seen through the perspective of a Cambodian photojournalist. When I learned that these characters were based on real people and that the movie was an account of actual events, it was mind-blowing.
LIFE CHANGING EVENT FOR ME
So, when I finally had the ability to travel anywhere in the world, I chose Cambodia. That first trip—of what eventually became two dozen trips there so far—changed not just my life but also the way I viewed the world and its events. It made me question where the narratives I always believed came from.
TIPS ON CHOOSING WHERE TO GO:
Choose the Type of Destination.
Find cities that have a connection to your interests and hobbies.
Look into countries inspired by your favorite films or books.
Start with less risky regions if this is your first rodeo.
Consider countries where English is more commonly spoken as a second language.
Use the post-it method to keep organized.
The world is at your fingertips, literally. Grab some Post-it notes, map out where you want to go and figure out what you want to do when you get there.
UNDERSTANDING YOUR CAPABILITIES
Source: Open AI. Created by Me.
I get it—you want to dive headfirst into an adventure and head somewhere wild, like Northern Iraq or Haiti for your first trip.
But here’s the thing: if you’re new to this, don’t have local contacts, and lack experience and street smarts, it’s wise to take your time and build up your skills first.
CHARACTERISTICS OF CHALLENGING DESTINATIONS:
Political instability and systematic corruption.
High stranger-on-stranger crime.
Lack of infrastructure for travelers.
Cultural and ideological complexities.
The president is wearing Ray-Ban Aviators in his state portrait.
I have been to all these places and even lived and worked in active war zones. I won’t BS you—it’s as cool as it sounds. You will encounter raw, unfiltered reality and people who are unapologetically true to themselves in ways you can only witness in such environments.
PREPARATIONS FOR HIGH-RISK TRAVEL:
Research, research, research.
Talk to people who live there on apps like Tandem, Italki, Preply, and HelloTalk to get the “word on the street” and learn essential phrases in the local lingo.
Take a Hostile Environments, Non-Permissive Environment, or Austere Environment Survival Course.
These places demand a certain level of instinct and experience that only time on the road can develop. Even for seasoned adventurers, venturing into dangerous areas often results in getting ripped off, scammed, beaten up, or worse. Sure, it might still make for a great story that you got the breaks beaten off of you by four working girls and spent the night in jail in Argentina, but it could also end with a very different outcome—like a trip home in a box or a $20K “fine” to get out of jail.
FIRST TRIP ADVICE
START WITH CHAOTIC METROPOLISES AND THE LESS-DEVELOPED COUNTRYSIDE
For first-timers, I recommend starting with places that are adventurous but manageable. Southeast Asia or some countries south of Texas are perfect choices. Even experienced adventurers like myself often use these areas as home bases, even after decades of traveling in the world’s most dangerous places. When you’re working on your next big adventure, it’s nice to be in a place where you don’t have to worry about getting kidnapped while grabbing a cup of coffee.
EARNING YOUR STRIPES
Travel to these regions, get your explorer sea legs, and develop the instincts you’ll need for the more dangerous destinations. Once you’ve gained experience and confidence, you’ll be ready to tackle the places that make your mom cry the moment you mention your plans.
WHAT TO DO WHEN YOU GET THERE
Landing in a strange country and being immediately approached by a taxi driver asking, “Where you go?” Checking into your hotel and looking out the window at a world you’ve never seen with your own eyes before. Grabbing a bite at a street food stand, surrounded by moto-taxi drivers on one side and a brand-new BMW on the other.
FOR THE PROFESSIONAL ADVENTURER, THE TRIP ITSELF IS THE ACTIVITY.
It’s about having drinks at a backpacker bar, where people let loose, knowing they’ll never see each other again, leaving inhibitions at the door. It’s wandering through a bustling night market, haggling over a “genuine” Rolex, or getting an hour-long massage for seven bucks. Spending the afternoon exploring a thousand-year-old temple, then topping off the evening with happy pizza and a cold beer alongside fellow travelers you just met.
This is the adventure—the unpredictable blend of sights, sounds, tastes, and experiences that make every trip unique.
CATEGORIZING YOUR ACTIVITIES
For my second trip to Cambodia, I had a list of things I wanted to do and places I wanted to see. To stay organized, I broke them into two categories: “Experiences” and “Places,” using my trusty Post-it note method.
Next, I divided each category into two groups: “Must Do” and “Want to Do, but if I don’t, I’ll save it for next time,” all ranked in order of importance. Once I had everything sorted, I stuck the Post-it notes into a composition book that I brought along with me.
When I arrived in Cambodia, I took all the Post-it notes out, stuck them to my hotel wall, and got to work. Each day, I would tackle a note or two and cross them off as I went. It was a simple but effective way to stay on track and make the most of my trip.
BUDGETING ADVENTURE TRAVEL
Source: Open AI. Created by Me.
I’m not going to dive too deep into this—you’re smart enough to know basic addition and subtraction, so you can figure out how much you have to spend and ensure you don’t blow it all in the first three days. Use the internet to your advantage. Check platforms like Reddit, YouTube, and great travel blogs (like the one you’re reading right now) to get estimates on how much things will cost in your destination.
THINGS TO ACCOUNT FOR IN YOUR BUDGET:
Flights
Accommodation
Approximate cost of daily meals and snacks
Entry fees for attractions and activities
Bars and clubs
Travel insurance (if you decide you need it)
Visa fees or other required documents
Unexpected expenses
Emergency cash
Souvenirs and gifts
Local transportation (e.g., taxis, trains)
Tips and gratuities for services
Throwing-around money
Buying things you need for the trip
Any bills you have to pay back home
WRITE DOWN THE ABOVE ON A POST-IT NOTE AND APPLY THIS SIMPLE BUDGETING EQUATION:
Add all of your expenses together = ???
Next, calculate the total (your Y), and then add 15% for price fluctuations = Z.
Slim down or chop activities, the number of days, or other expenses until your budget aligns.
IN A NUTSHELL:
Y + 15% = Z → +/- Adjust as needed until it fits your budget.
Bada bing bada boom! Now you have a budget.
CASH OR CREDIT FOR EMERGENCIES?
This is one of the rare instances where I say put it on a credit card if you have to. I normally am against using a credit card to pay for travels because it ends up becoming a borrowing-from-Peter-to-pay-Paul Ouroboros financial situation. This is an exception to the rule for emergencies only because credit cards are the fastest and sometimes the only way to make a large, on-the-spot payment overseas.
And because you will not have to set aside a portion of your adventure budget cash for emergencies, thereby decreasing the amount of money for your trip. So whether it’s paying for a stay in the emergency room or booking a last-minute flight because your mom is sick, in this instance, use a credit card.
TWO CARD SYSTEM
I highly recommend carrying two credit cards with decent credit limits at all times on your travels. There’s a saying in the Army that goes like this: “One is none, two is one.” A backup credit card can save the day if your primary card gets lost, locked, stolen, or declined. Don’t forget to go on your credit card’s app and turn on international purchases or call them beforehand.
Having an emergency fund plan in advance for the unexpected gives you peace of mind and ensures you can handle any situation, and if you (hopefully) don’t use it, then it costs you nothing and only took ten minutes to prepare.
PARTING ADVICE
Traveling is as much about preparation as it is about stepping foot on the plane, train, or automobile to your next adventure. Starting with a dream, then organizing your tasks with Post-it notes to budgeting and researching your destinations, every step you take moves you closer to your goal. Sure, spontaneity is a big part of what makes travel exciting, but there is a difference between the spontaneity of taking a speedboat trip on the Mekong Delta with some French backpackers you met in a bar 20 minutes ago, and forgetting your international driver’s license or running out of money halfway through. Having the framework completed in advance will make all the difference between an unforgettable trip and a stress-filled, haphazard one.
TIME IS ON YOUR SIDE
Start medium speed, gain some experience, and you will develop the instincts and traveler street smarts that you will need on riskier adventures down the road. I hate to sound like a broken record here, but the journey itself is almost always the most rewarding part of the experience. By being prepared and organizing your travel framework before you start your trip, you will then be able to fully embrace the spur-of-the-moment opportunity because you will have a clear mind.
ADVENTURE IS CALLING—YOU JUST NEED TO ANSWER WITH A PLAN
Adventure Awaits!
