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How to Vagabond: Complete Guide to Long-Term World Travel

Most of us travel short-term. At most, a few months during the summer. But there's a different way to travel long-term. Here's how to vagabond.

Most of us travel short-term. At most, a few months during the summer.But there's a different way to travel.It's travel that doesn't have a deadline, nor a specific agenda. It's called Vagabonding.

Vagabonding is about taking time from your normal life to explore overseas for an extended amount of time. It could be for half a year, a few years, or even a lifetime for those daring individuals.

Enter Rolf Potts

The person who popularized Vagabonding is Rolf Potts, with his bestselling book Vagabonding.

Before writing his book, Rolf has reported from more than sixty countries around the world for some of the world's most recognized media outlets, including The New York Times, Slate.com, Sports Illustrated, and more.

Learn more about Rolf here.Today, his book Vagabonding is recognized as 'the bible' for all aspiring travellers, and is known to have inspired many travel influencers around the world, including Tim Ferriss and Matt Kepnes.

"In my view, if long-term travel and backpacking had a bible, this would be it."-Matt Kepnes, Founder of NomadicMatt.com

Travel is Not a Wealthy Person's Sport

One of the biggest arguments (in our opinion) that Rolf makes in Vagabonding, is that travel does not have to be a wealthy person's sport. Nor is long-term travel meant to be a trend.

Thirty years ago, this may have been a different conversation. Information wasn't nearly as accessible, online communication tools didn't exist, and transportation wasn't as efficient, and therefore more expensive.

Today, the world is more connected than it has ever been. Most of us know how to speak a second language, we can speak to anyone in the world in seconds, and most importantly, the costs of travel have dropped significantly.


Some have gone as far to claim that anyone can travel the world with $50 USD a day. And there are even those building successful companies while traveling/living across the world, including Buffer, Wordpress, Toptal, and our company Rype.

How to Get Started

Before we go any further, we should mention that this isn't meant to be a typical 'how-to' guide on Vagabonding. There is no 'specific' way to vagabond, since it's going to be a different experience for everyone, depending on your purpose of travel, length, and where you go.What we will provide are tips and guides to help you get started that we hope will be valuable, no matter where, when, or what you want to get out of your vagabonding experience.

Financing your travels

This is probably the biggest hurdle that most aspiring vagabonders face. The lifestyle of vagabonding does not necessarily require more money than your regular lifestyle (depending on what your personal burn rate is). But needlessly to say, long-term travel requires money to support your day to day lifestyle.Here are just a few creative ways that have been tried and true.

  • Find an opportunity overseas: there's a few ways to go about this, whether it's getting transferred to an overseas office at your current job, or finding work overseas.
  • Start an online business or a 'muse': making money online has never been more possible than today. You can start a website or mobile app for less than $100, and run your entire company from your laptop. *Note: This is also how Rype runs its operations.
  • Rent out your current place: using AirBnB, craigslist, or other rental listing services, you can charge a premium price for short-term stays at your current place, while you are traveling overseas.With the right location, you'll be surprised how much you can make -- just make sure you have someone you trust to manage it for you.
  • Offer consulting: before we started Rype, this is how I personally funded my travels around South America by consulting companies in the US. The majority of the small funding to start Rype also came from this income source! Here's how I got 30 consulting offers in 30 days.
  • Teach a language: you could also teach a language that you already know, such as English or Spanish. There's no shortage of people who want to know how to speak a new language.
  • WWOOF (or other volunteer initiatives): which stands for World Wide Opportunities on Organic Farms is always looking for new volunteers to help out. In exchange for your labor, you'll get food and accommodations covered by the farm you're assigned to.

Where to stay

  • AirBnB: The great thing about AirBnB is your ability to book places on-demand, with their feature Instant Booking. With over 34,000 cities around the world (at the time of this writing), you're sure to find a place to stay.
  • Couchsurfing: If you're seeking a free solution to accommodation, you can check out Couchsurfing. It's also a community of travellers, which enables you to meet and be hosted by like-minded individuals wherever you go.
  • Nomad List: As a digital nomad, finding places that are affordable, start-up friendly, with great internet are rare, but golden gems. This is a great place to start if you want to figure out where you want to stay.

Getting there

Once you've figured out how you're going to be financing your vagabond, and how you're going to get there, it's time to figure out how you're going to get there, in a budget-friendly way.

  • Spirit Airlines:Spirit Airlines is recognized as one of the cheapest airlines in the world. They offer a lot of upsells, which is how they generate a lot of their profits. It should also be noted that the airline flies only to select places around North America, Central America, and South America.
  • Flight Aggregators (Kayak, Hipmunk, and Skyscanner):Using flight aggregators are also a great way to find the cheapest or most convenient flight tickets in the market. Make sure you use Incognito mode if you're visiting any flight ticket websites, as they can often increase prices if they know that you're a return customer within a certain timeframe.*Hipmunk also has a useful feature called Price Graph, which shows you the price of your desired travel destination within the next 90 days.
  • Visa requirements:CheapoAir’s tool is a great place to check if you need a visa to enter a new country

Things to prepare

We'll skip over the basic necessities, such as your passport, phone, wallet, laptop, and other essentials.Here are key things you may want to pack to prepare for your long-term vagabond:

  • Ethernet cable: WiFi will not always work. Especially when you least suspect it!
  • Unlocked smartphone: This will allow you to buy a pay-as-you-go local SIM card, whenever you visit a new city. Unlocking your phone will only cost around $50-100, but it will be well worth it over time in terms of saving you money and time.
  • Kindle: There's only so many books you can carry with you. With Kindle, you can download as many books as you want, without taking up any more space.
  • Skype number: This is used as a secondary number in case something happens with my main phone. You can also use Skype to make international calls for a small charge, if you don't have international calling on your data plan. Highly useful.
  • USD dollars: The US currency is highly exchangeable, and is known to be a more stable currency to the outside world than other currencies.
  • Currency converter: Currency prices are always changing on a daily basis. Using a currency converter app can help you get the best exchange deal for your money.
  • Timezone converter
  • Notebooks/Journals: One of the best parts about long-term traveling is discovering new things that you didn't know about yourself, or uncovering great ideas when you least suspect it.
  • Portable stretch balls: Trust us, these will come in handy! Acuball is a portable one we suggest.
  • Ibuprofen: For any injuries, general pain, or headaches.
  • Copy of your passport: If there's anything to have another copy of when overseas, this is it.
  • Running shoes
  • Portal chargers & travel adapters

Did we miss anything important? Share in the comments section for people to explore.

Length of travel

There is no right answer for this. However, practically speaking, 3 months is an ideal timeline to shoot for if you want to live in several places while having enough time to enjoy your current city.This is because most places have a 90-day rule for tourists, where you have to leave the country and return if you want to stay for longer than 90 days.

Again, use CheapOAir's visa directory to check if you require a visa before visiting!Here are some reasons why ~3 months is the ideal amount of time to allocate for:

  • Constraints of a typical visa as a tourist (as mentioned)
  • Time to relax, explore, and focus without stressing yourself out:The advantage of vagabonding is your ability to live as if you're a local while in the mentality of a temporary visitor. You can be adventurous without rushing to complete everything on your must-see list.
  • Reduces cost:Having a longer term stay than just a week allows you to negotiate special terms on housing, cars, etc.

Recognizing the downsides

It wouldn't be a complete guide on how to vagabond, without mentioning the downsides of long-term traveling. Like everything in life, the grass is greener on the other side, so it's important to know what you're sacrificing when you vagabond, such as:

  • Saying good-bye as often as you say hello
  • Maintaining friendships you meet while traveling or back at home
  • Sustaining love relationships you foster while traveling or back at home
  • Getting tired of traveling
  • Homesickness

Ultimately, long-term travel takes a certain type of person to enjoy over time. And even those that fit the profile will likely get tired of the constant traveling, and it's useful to know this before you experience it.

The Mindset

This is perhaps the most important part to nail down before you begin your vagabond experience.

Things will go wrong, especially when you least suspect it. Be focused enough to have a sustainable plan, but flexible enough to steer through the grey clouds of unexpected obstacles during vagabond experience.Long-term traveling can be one of the most amazing experiences anyone can have. You just have to develop the right mindset, and embrace the inevitable diversions along the way.

"As for the tourist-circuit, slowing your travels down will automatically lead you off the tourist trail. When you aren’t racing from 'attraction' to 'attraction,' you’ll quickly discover that the best experiences come from the diversions along the way."-Rolf Potts

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