Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel - Deepstash

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It means taking an extended time-out from your normal life to travel the world on your own terms.

Vagabonds work only to travel. They travel solely for the sake of traveling, and therefore earning money is part of their mission to earn the freedom to do just that.

So vagabonding doesn’t start with picking a departure date at the travel agent or arriving at the check-in counter at the airport. It starts with saving money, poring over maps, figuring out your destination and your why, and finally stopping to make excuses and putting off your journey.


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“The value of your travels does not hinge on how many stamps you have in your passport when you get home -- and the slow nuanced experience of a single country is always better than the hurried, superficial experience of forty countries.”



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Change Your Relationship With Money

Our relationship with money makes us see travel as a luxury, which is why we think of “a vacation” just like we think of a new car or an expensive TV – it costs a ton of money and is a one-time thing.

But tightly packed, stressful, calculated flat fee holiday cruises with a fixed budget provide none of the rich experiences travel is really about. If you think there might be a vagabond inside you, the first thing that’ll have to change is your relationship with money.


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Constructive Quitting

Constructive Quitting

It means negotiating with your employer for special sabbaticals and long-term leaves of absence.


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“Work is when you confront the problems you might otherwise be tempted to run away from.”



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Simplify Your Life For Vagabonding

Simplify Your Life For Vagabonding

  • Stop expansion. Don’t add any new possessions to your life
  • Rein in your routine. Live more humbly and invest the difference into your travel fund
  • Reduce clutter. Downsize what you already own (and sell it to make extra money).

The goal of preparation is not knowing exactly where you’ll go but being confident nonetheless that you’ll get there. Your attitude is more important than your itinerary.


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“The simple willingness to improvise is more vital, in the long run, than research.”



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The People You Meet On The Road

Vagabonding revolves around the people you meet on the road — and the attitude you take into these encounters can make or break your entire travel experience.

  • To know how to conscientiously spend money on the road, watch what the locals do.
  • Be sure to carry photos of yourself, your hometown, and your family to show to people on the road.


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Bridge The “Language Gap”

Bridge The “Language Gap”

  • Speak slowly, simply, and clearly
  • Be patient and try to figure out mispronounced words from the context of what is being said
  • Compliment anyone brave (and helpful) enough to try his or her English on you
  • Develop a knack for cross-cultural small talk
  • Commit a few words and phrases of the local language to memory.


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Life on The Road

  • If in doubt about what to do in a place, just start walking through your new environment
  • Don’t make too many arrangements at once as it stunts your spontaneity. Only make advance reservations for one trip at a time
  • Wash your own clothes with shampoo.
  • Rooms are easy to find so don’t bother with reservations. Exceptions: local festivals, high tourist season, or when you’re arriving at night
  • Never check into a room without asking to see it first
  • Don’t put your bags into the trunk of a taxi, as this is often used as a bargaining chip by dodgy taxi drivers
  • Pre-trip immunizations are vital.


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  • If you can cook it, boil it, or peel it, you can eat it — otherwise, forget it
  • Look for establishments with lots of customers and healthy-looking employees
  • When ordering meat, make sure it’s well cooked. Be wary of milk, “beef”, leafy salads, and shellfish
  • Avoid non-purified water (ice included) and make sure your bottled water is sealed
  • Keep in mind that a restaurant’s food isn’t necessarily healthy (or clean, or tasty) merely because the place has an English-language menu and serves up pizza, club sandwiches, or an “American” breakfast.


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Crime and Scams

  • Avoid bringing expensive or irreplaceable items 
  • Don’t brag about the wealth you do have 
  • Keep cash in discreet places like a money belt, a sock, or a hidden pocket. Be wary of public distractions and dense crowds. This is where pickpockets tend to operate
  • When staying at a hotel or guesthouse, keep your extra cash in the safe
  • Be wary of pushy new “friends” who insist on giving you free shopping or sightseeing tours.


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Vagabonding Is A Rediscovery Of Reality Itself

Vagabonding Is A Rediscovery Of Reality Itself

  • Let go of your pre-trip stereotypes and exchange two-dimensional expectations for living people, living places, and living life.
  • Fall into a nightly ritual of partying and you might overlook the subtlety of places, stunt your travel creativity, and trap yourself in the patterns of home.
  • Creativity is particularly important after you’ve been on the road for a long time, because inevitably you’ll fall into a kind of road routine.


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Coming Home

  • Returning home can be weird. Everything will look like it did but feel completely different at the same time.
  • It’s hard for friends to relate to your travel experiences because they don’t share the values that took you out on the road in the first place. So remember to keep your stories short and save the best bits for yourself.
  • Hitting the road to get travel out of your system rarely works, so the best remedy upon returning home is to make travel a part of your system.


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Operations geologist

Not just a plan of action, vagabonding is an outlook on life that emphasizes creativity, discovery, and the growth of the spirit.


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