Traveling in the Worst Situations

I don’t keep record of my travels, despite so many people that encourage me otherwise. There’s so much information on the internet, and google is ever so powerful, that I worry any advice or experiences I have to offer are already available online, like how to sleep outside anywhere, what are the cheapest ways of acquiring food, and how to make money on the road. In fact, I tend to keep a low profile online on social media (Facebook, twitter, Instagram, etc.) and while traveling, but that’s just me. The point is I don’t have too much experience transcribing my journeys, but I think this is something that can be vital for traveling in many ways. Knowing how to travel in what may be the worst situations you’ll find yourselves in is important not just for persevering through those situations, but also as reassurance while traveling; that you know how to get through the worst.

Some of these tips may not be relevant to your climate or style of traveling (I travel by bike and use a hammock), so I’ll try to make them as universal and applicable as I can. Also, some of this may be obvious to some people; even if it is, its repetition has value in underlying and reminding you of it’s importance.

Finding somewhere (anywhere) to sleep

Basically, find somewhere with few or no people, where people can’t see or notice you, and where they wouldn’t care that you’re sleeping there. For starters, avoid cities since there’s a lot of people, so you’ll have little in the way of privacy and safety. I travel by bike and thus have always been able to escape cities by nightfall, so I don’t have much to offer if you can’t make it out other than that the further away from downtown you travel, the easier it will be to find somewhere to sleep. Try to start looking at least an hour before sundown, earlier or later depending on what your prospects look like.

Avoid what would be considered a family place, like residential neighborhoods, nature trails, and especially parks. You want somewhere where not only is there a low frequency of people in the area, but also a low chance that they’ll care enough to bother you, or you bother them depending on how you look at it (better to think from their perspective). It’s important you choose a spot that no one care about, not someone’s backyard, or private property that is marked as such or has signs of frequently being used.

Once you find a place that cannot be easily viewed from where people are (road, sidewalk, nature trail), walk in briskly while there are as few people that’ll notice, but try not to look suspicious, just do it. Once you’re in, walk in at least 50ft or as far away from the roadside as you can, choosing somewhere to sleep isn’t the time to be lazy. Try to be mindful of how much noise you make, and time it with passing traffic, roadside construction, or something else, and not just while you’re setting up camp, but for your entire stay. If you can still see where people pass by clearly and not very obscured, travel as far in as you need to, or make sure it isn’t somewhere they’d think to look, like 10ft higher. Trees are your friends (especially hammock users); careful using a light at night. Some examples of good places might be just off the highway out of town, behind a super shopping center like Wal-Mart, or close to train tracks.

It takes a lot of experience, careful consideration, and courage to sleep anywhere, things that aren’t very easy to relay through writing. Even if you don’t end up using and practicing these skills, you can keep them sharp by just looking while you’re walking/biking/driving by new places for what would hypothetically be a good place to sleep if you had to, like a game. Before you know it, you’ll start playing it a lot during boring car rides.

Sleeping outside in freezing weather

Don’t travel somewhere with below freezing temperatures if you expect you may need to sleep outside, it’s a terrible idea. But if you decide to do it anyway, hopefully this helps.

Big cities can be helpful. You can sleep in train/bus stations, although you may need to buy a ticket to do so, in which case buy the cheapest one. You can sleep on the subway, especially in a big city like New York.

If you’re camping, better to do it with a tent and not a hammock, but if you use a hammock I can offer several tips. Make sure you eat enough food, preferably something warm and meal-like (not pop-tarts) a few hours before you sleep. Start looking for somewhere to camp at least an hour before sundown. You’ll want to find somewhere that is not low in a valley or ditch (more cold air, less sunlight) or near a lot of water (humidity). Find a place that will have sunlight as early in the morning as possible, and little wind, which presents a dilemma because places with a lot of sunlight like open fields and hills/mountains will have more wind, and things that block wind like trees also block sunlight.

Now here’s the issue with sleeping in a hammock in cold weather. The insulation underneath you will be compressed by your weight, so heat is easily sapped by the air beneath your hammock; this is the worst part. Set your hammock as low to the ground as you can, and break off any branches that will rob you of your glorious morning sunlight. Line your hammock with all of your clothes (even towels, rags, bandannas, scarves, mitts, etc.) and even your backpack if nothing sticks into your back.  Try to put more near where your bottom will be, since that will have the most compression and lose heat the easiest. Put your sleeping bag in there. If you have a fly/cover, wrap your hammock with it like a cocoon, but make it so you can easily open it to allow sunlight in once it’s morning. Do anything you need to do before you get in, gather everything you’ll need for the night in your hammock, including whatever food you have left for breakfast. Once you’re in, you won’t even want to turn over until the sun comes out. Once you’re in your sleeping bag, close the draw string as tightly as you can, and use your hat to seal the hole and create your ice coffin.

If it really is below freezing, you’ll probably wake up around 3 or 4 in the morning, since that’s the coldest time of night. It could very well be too cold for you to even sleep, which is a terrible feeling. Make sure you curse yourself for making such a foolish decision. Morning does come eventually though, whether you sleep or not, and if you’ve planned correctly, you’ll take off your fly/cover and be welcomed by the warming rays of the morning sun, which feels like a nice warm blanket, or the light at the end of a cave. Go ahead and enjoy it while eating your breakfast in bed after a grueling frigidly treacherous night of cold; laugh at the frost on your hammock as it melts away.

Even if you feel fine the next morning, try avoid sleeping outside in freezing weather 2 nights or more in a row, your immune system will be weakened and you’ll get sick (disclaimer: I’m not a medical professional in any way).


If people could simply summon the motivation to do what they want anytime they please, life would be incredibly more convenient and simple. Unfortunately people don’t always have enough willpower, even if they need it. Miguel has already written a lot about what type of traveling philosophy he has, and many people I’ve met share a similarly positive attitude.

But people are very different and much more complicated when looking into the depths of their character or the sources of their principles; simply put, the methods and mechanisms that some travelers use to persevere and find their inner strength in dire situations may not be effective for others. Everyone has their own attitude, guiding life philosophy, and aspirations. It’s vital to understand yourself so you can develop your own methods to endure difficult situations. One of my methods is creating a music library with a variety of different types of songs that match whatever situations or feelings you face (especially biking).

You’ll learn a lot about yourself simply by traveling through terrible situations, seeing how you react in the face of extreme and unprecedented adversity, how you respond to stress and what strengths you can rely on and what weaknesses you need to worry about.


In your worst times, you may find yourself dirty and smelly from not having a shower for weeks, tired and depressed from road fatigue, loneliness, and simply no longer finding purpose in your travels. Your social interactions become more awkward from isolation and simply not even wanting to have conversations. Even worse, you may even find yourself in humiliating and shameful situations, doing things you’d never think you’d do, feeling and accepting that you now belong in a lower social class then you’ve ever lived in, and no longer recognize yourself or even remember who you were. Add in people who start mistaking you for a homeless person or someone who’s just terribly down on their luck and maybe then you’ll start considering the value and nature of dignity.

It’s amazingly humbling and eye opening, especially if you’ve had an easy childhood. You suddenly start living in a different world. Some people will stay away from you, others will be more interested. They may feel pity and concern for you, and want to help in some way. Some may open up to you about their own struggles because you seem like you’re in a position to truly appreciate what they’re saying and empathize with them. You’ll hear stories of someone who works 80 hours a week to be able to afford their cancer treatment, or someone who lets you know that the burger joint across the street is hiring because it looks like you can use a job. You start talking and he tells you how he just had a gun pointed to his face today because his brother is a drug dealer and he’s desperately trying to hold down a job and get out of that environment when everyone he knows is either in a gang or in jail.


Reading all of this might feel strange, especially if you’ve rarely traveled alone. Many of these cases are pretty extreme and unfamiliar to many people, but regardless of what situations you are faced with, all travelers have their own unique set of problems, so hopefully whatever happens on your travels, you’ll find some way to make some of this useful to you.

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