Test Dummy Guide to Planning your Backpacking Escape

Have you pondered leaving all the dregs of life to go chase your pink dragons in foreign paradises. Lying I would be, if I said I wasn’t. If you’re like I was, working a full time job with hopes of escape in the future then you’re in good hands! I’ll hold your hand through the practice of planning your backpacking escape. I’m far from the first person to do this yet I’m shocked by all the people that say “I wish I could do that”. Hey you! You can do this, here’s how…

Planning for Planlessness

Oh my… I really didn’t plan for this to get stolen…

It’s taken years of planning for the future to realize: plan for activities not for an itinerary you expect to adhere to. Last year if you asked me where I would be next winter, I would have told you Argentina. Had you asked me the same thing a year prior I would have said Italy. Both winters there was a slight miscalculation and this thing called life happened. In one case my landlords in Berlin offered me and my startup partner a room in their newly opened international house in Barranquilla, Colombia where the cost of living would be half that of Berlin and the weather more bearable. The following year I happened to get my shit stolen while backpacking through Ukraine and decided saving up in New York City might be a smarter choice than Argentina. As a traveler who’s trying to stretch his dollars, I can attest that the perfect deal to where you want to go usually doesn’t appear when you wish it so.

Many a time have I been clueless to this lesson. Since my job folded early 2017, I have reverted back to travel mode, meaning I plan to see as much of the world as I can. Now that I’ve finally admitted to myself that I can’t predict my future I am planning only two steps ahead. I am flying to the Azores island of São Miguel, Portugal in the Pacific very very soon. Have I ever heard of these islands? No, but camping a week on an island is more enjoyable then a 4 hour layover on it.

Having an End Goal Helps

With that said, it does help having at least a general direction to guide you, something like: reaching a destination, acquiring a skill, or completing an undertaking.

Visualize the end goal!

In my case my goal is reaching Vilnius, Lithuania from Porto, Portugal without flying. My planned estimated dates of arrival are… lol, I’ve learned better than trying to predict that far ahead. Instead I have everything planned from Porto to Santiago de Compostela and I’ll decide what I want to do next–should I hike the Camino de Santiago backwards towards France or hop on a boat going north? I dono…

It’s very hard to predict what you’re going to want there while you’re still here

Imagine you’re going to Asia for the first time and you booked a packaged tour with your flight. I’m willing to bet my left pinky this agency knows about this part of the world. Though you may not like everything on their itinerary, they’re likely to captivate you on some of the excursions. Let’s say, while traveling with your tour group you fall in love with the foods of the cities much more than the white beaches and elephant rides. You had no idea that the food here could be so foreign yet so delectable! How could you have known from your living room computer half a globe away when you booked the trip?

How lovely would it be to have more time to invest in the parts of a city that you love most? I’m not saying you should avoid packaged trips, I think they’re great for getting our feet into the lands that we otherwise wouldn’t have the balls to. All the same I have no idea what I’ll want to do after I arrive in the next place I can only surmise.

Options on the Road

If you can recall the last time you felt wanderlust then you can relate to the insatiable desire to fast forward to your trip date. If you get that feeling often then you might as well put that impatience to use and give yourself options for when you finally do arrive. At one point I went through a phase of plotting everything I wanted to see in Europe and this is what I got.

I wanna see it all!!!

You can’t know what you’ll want to do when you’re still home but you can give yourself a buttload of choices. Last year I discovered Google’s My Maps and I find it invaluable for plotting activities once you arrive. Furthermore by researching ahead of time, you’re often able to save money by discovering less well known options that may not have the biggest ad or may not overtly want to attract tourists.


An Inventory of all your Gear

I found it usefully to keep track of everything I’m bringing with me in a list. At the very least once I reach my destination I’ll have a good idea of what I brought with me which I really shouldn’t have. Otherwise keeping a list is a valuable tool for actually packing your bag.

I’m using Google Sheets for now and by having everything a single list I can start arranging items by frequency of use and I can plan modularly.

Sleeping bag, tent, inflatable air mattress, cooking pot, first aid kit, electronics bag and toiletries

By batching I can keep my electronics, toiletries, cooking and first aid gear together and by having everything in a list I can account for even the small things. The next step is to


Here’s an invaluable trick I’ve picked up over the years of living out of a bag from Asia to Europe. The trick is to pack then repack then do that some more. Your backpack(s) will contain almost, if not everything you will need. On one hand it is good to have everything you may need, on the other hand, a flashlight in your bag is no good in the dark if you don’t know where it is, when you need it. By repeatedly packing and repacking you are continually reacquainting yourself with all of your clothes and accessories. Thus I was able to find better combinations for items; keep the sleeping mask and ear plugs in the toiletries bag, etc…

Packing Frequent Access Items. If you do end up making an inventory then it’s helpful to get a good look at items that you may need frequent access to; items like chargerscableswater and sunglasses. To make my life easier on the road I practiced for certain situations like: finding a flashlight in the dark, getting out my phone charger or finding the spare camera batteries. While still home is an ideal time to figure out what is inconvenient and where it makes better sense to store this-and-that.

Similarly I packed routine items, or items which you may need every day but not more than once or twice a day, together. Items such a toothbrush and clean socks are 2 examples that may pertain to your hygiene routine. It makes sense to keep these items together. I packed all of my non-dirty clothes into a compression sack which I will ideally only have to open & recompress once a day. Thrillist also has a good article highlighting some military packing tips not mentioned here.


I hope any of these tips, lists or maps are useful in planning your backpacking escape. If you have questions or comments I’d be happy to hear in the comments below. With that said and backpacks packed, I say, Adios America!