Estimated reading time: 9 minutes
PLAN YOUR OWN ITINERARY BY KEEPING IT SIMPLE.
If you haven’t read Vagabond Secret 2: How to Conquer Travel Anxiety, do that shit now.
Find one thing you want to do more than anything and make sure it gets done: this is called your Vagabond Adventure. Plan around that one thing. Some people get overwhelmed by choices and outsource the decision-making process to a tour guide they found online or some all-inclusive hotel, but a vagabond adventure will make your itinerary easy to plan and simple to research. It serves as the central goal of your trip to alleviate any fear of not making the most of your time or missing out on something you thought you should’ve seen. With your mind now at rest, you have space for adventuring, relaxing, seeking, or drifting.
Your vagabond adventure is the one thing you need to research, and it’ll be the foundation you’ll build your trip around so you can shape other sub-adventures accordingly while you’re there (for longer-term travelers) or before you leave (for short getaways). It should be something that exhilarates you. Make a promise to yourself that it will get done no matter what. For example, I made a promise to circumnavigate South America at all costs, to break the Guinness World Record for Longest Journey by Car in a Single Country, go paragliding in Colombia and to jump off a fifty-foot cliff in Argentina.
Here are some vagabond adventures on my list… I want to take the Eurail to as many countries as I can in one month. I love trains, staring out the window at my surroundings, and random conversation with random people on a random train. I want to master three languages other than English and go to every country in Africa. All these ideas really excite me. Adventure can be anything that makes you feel excited—even learning a new language…
What excites you?
A great way to pick your vagabond adventure is to ask yourself: if there was only one thing I did while away, would it be? Would you feel accomplished if that one thing got done? The answer must be yes for it to make the cut. For example: Hiking Machu Picchu, seeing the Great Wall of China, doing one hike in Antarctica, road-tripping Zambia, or studying Italian in Bolzano. Once you know the core mission of your trip, every other day you’re not involved in that activity becomes fair game for extraordinary creativity. Rent a car and drive up Finland’s coast and camp out beneath the Northern Lights. Take a snowmobile down the Yukon River in Alaska during the winter when it’s covered with snow. Skydive in New Zealand or go visit Lalibela in Ethiopia. Single missions keep us focused. When you’re on the road, wandering is fun, but it can become unfulfilling if it’s the only thing you’re doing. In other words, if you’re not sure what the point of your trip is, you may begin to feel aimless and bored.
Sometimes you want to do too many things and can’t settle on one core vagabond adventure, which makes it impossible to plan your trip without overpaying a tour guide or scrambling to a million attractions at once for fear of missing something. Unless you’re in a city for quite a while, you won’t be able to do everything it offers. A great way to whittle down your options so you don’t fall into decision-paralysis and end up staying at your hostel all day flirting with the Danish girl by the hammock wondering what you should do with your day (or maybe that’s just me), is to define your vagabond adventure and spend your time researching only the best way to do that.
What is irreplaceable?
Another tactic to keep the wanderlust in check is to ask yourself: is there anything I want to do that can be done elsewhere? For instance, you might want to go paragliding while in Medellin, take the graffiti tour and walking tour, and also view one of Pablo Escobar’s houses. But if you don’t have time to do it all, cross off anything you can do in other places. The graffiti tour is specific to Medellin, the walking tour is specific to Medellin, all the millions of Pablo Escobar tours are specific to Medellin, but paragliding can be done in many places. Cross out anything that can be done elsewhere if you’re short on time. Do what can only be done in the city you’re traveling to or you might regret not doing it, and regret is the one word we are trying to stay away from at all costs.
Try not to go for comfort; this isn’t a vacation.
Travel and vacation have nothing to do with each other. Travel is the art of leaving your comfort zone to explore yourself trekking through the unknown. Vacation is the practice of leaving your life and going to a comfort zone for a short period of time. It’s one of the worst things on the planet. As Rolf Potts, author of Vagabonding, puts it: “No combination of one-week or ten-day vacations will truly take you away from the life you lead at home.”
I couldn’t agree more. Odd as it may sound in a book on travel, vacation is simply a ticking time bomb back to real life. It’s the epitome of anxiety. It’s like doing cocaine. That first day (line) is great, but every day (line) after that, you’re staring at your phone (coke bag):
Only four days (lines) left.
Only three days (lines) left.
Shit… better make the most of it.
Fuck, we leave tomorrow. I don’t want to go back to work (being sober). We better head to the beach ASAP (buy more drugs)!
So… you put on your bathing suit (take out money from your savings) and walk on down to the crystal-clear ocean and check your iPhone ten times in one hour to see how many work emails came in. You check to see what time it is.
3PM?! Oh no, only nine more hours of the day! Then it’s already tomorrow (the sun is starting to come up)! It’s a big countdown clock, that’s what vacation is. A giant countdown clock back to a life we don’t want. Don’t take vacations.
I’ll end that story by reminding you I’m sober and don’t do coke anymore 🙂
Plan as little as possible
Anyway, list out all the components that’re in line with your vagabond adventure. If your goal is to see every city in the country you’re traveling to, list out all the cities in your travel notebook and map out a potential route. Do you need to take a bus? Plane? Train? Carpool? What are your options? Plan as little as possible, but enough so that you feel like you know where your north star is. (By the way, if you don’t have a travel notebook… get one!)
If you’ll only be in one city and your goal is to see that city in its entirety, list out all the cultural components you want to experience while there; the cuisine, the geography, the city chaos, the brothels, the clubs—whatever your thing is, no judgment here.
Once you’re there, it’s quite easy to book a local tour on the spot. You don’t need to plan every sight you’ll see; it’s easy enough to do that in person. A better itinerary is to plan potential routes and what forms of transportation are available, the best way to contact them (mobile app, website, phone, etc). Once you know your vagabond adventure, you’re good to go. Then just fill in the blanks. Simply ask anyone at your hostel, your Airbnb host, the barista at the café, or your waiter: “what should I do today?” Everyone is more than happy to make suggestions about what to do in their hometown. Shit, I love when people come to my town and ask me what to do; I’m full of suggestions.
Travel red flags
Once you know what you want to do, if it requires a guide, just know all the guides are pretty much the same. It’s always a bit of a gamble, but there are some red flags to look out for: photoshopped photos around their office and not providing all the information up front (tour guide, tour guide’s contact information, lodging information, which meals are included, etc). Also, you want to know which adventure on their brochure you’d like to book before negotiating with them, and always negotiate. You don’t want to look like a tourist that can be taken advantage of. Even if you can afford it, negotiate. It’s not about the money, it’s about not setting the standard of being ripped off by every person in town. Get used to not accepting the first price.
With all that being said, find a happy medium and stay away from too many plans before you arrive. Just know your vagabond adventure, not your every day. Too many plans are dangerous. If you meet an Argentine cowboy that has swept your heart into the sky, you’ll want to know where to invite him to tag along rather than aimlessly having drinks at the bar across the street and killing valuable time. On the other hand, if your mission is to let anything happen (usually my mission) then go with what feels freeing. If that means canceling everything you were going to do to cross the border into Bolivia to see the salt flats with that Argentine cowboy, then go! Fuck it! Freedom at all costs!
However, I should say not all travel should be steered by what feels good. I don’t want to encourage methed-out sex in unkempt brothels (although I know that’ll happen anyway for some people), but certainly travel is the time to put on your fuck-it face and go wherever the hell life takes you. I view plans like contracts: I only refer to them if something goes wrong. Your vagabond mission will keep you focused just enough to allow you to venture out organically as you meet people along your journey and still have some sort of agenda. Besides, plans fall apart anyway. Nothing I’ve done in life has gone as planned. That doesn’t mean it goes bad, it just means whatever I was expecting usually doesn’t happen the way I envisioned it would.
Don’t waste time
When I was mapping out my route to break the Guinness World Record road trip, I stayed up till five in the morning pinpointing all the places I would stop at. It took me forever putting together a route that would satisfy both me and my then-girlfriend, but on the second day, we veered off course and never drove anywhere that I planned. However, my vagabond adventure—break the Guinness World Record—still got done. Although the route I carefully constructed fell apart, I still stayed on track. The path will reveal itself every day if you know where you want to end up, and it’ll probably come to you through random run-ins with locals and connections you make with other travelers on your trip.
The secret to making the most of your time is to know your vagabond adventure.
How to make a shift in your life.