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How to Organize an International Adventure

by | 26 minute read

Let me start by saying that what follows is not your typical daily blog post. At more than 7,000 words, it’s intended to be more of a reference guide for anyone trying to plan an exciting international adventure. You’ll have the best experience by bookmarking this page with a service like Delicious, StumbleUpon, or Evernote so that you can come back when you need to reference something.

I was going to publish this as an e-book, but since you’re a traveler and probably don’t need any more files to keep track of, I decided to release it as a comprehensive article that you can always get to wherever you may be on the globe. Enjoy!

Also, don’t forget to sign up for free updates from Riskology.co so you don’t miss any new content like this.

Update: Due to popular demand, you can now download this guide along with important updates as a digital guide in PDF format. To get your free copy, just go over here.

Table of Contents

2 Mountains, 2 Marathons, 2 Continents

As I’ve alluded to over the past few months, 2011 is slated to be a big year for my 1% Club.

I have plans that will be taking me to a lot of places and having a lot of really amazing experiences. The biggest adventure will be a month-long trip through Africa and Europe this June where I’ll be climbing two of the world’s tallest mountains and running two marathons.

For all the travel geeks out there, here’s what my actual flight schedule looks like:

PDX–>IAD–>JNB–>DAR–>JNB–>FRA–>WAW–>TXL–>DME–>MRV–>DME–>MUC–>
WAW–>MUC–>IAD–>DEN–>PDX

Funny tidbit: I’ll be in Germany four times over the course of this trip, but I’ll never make it out of the airport.

Here are the main highlights of the escapade:

  • Running the Big 5 Marathon on the Entabeni Game Reserve in South Africa among lions, elephants, buffalo, leopards, and a rhinoceros or two.
  • Climbing Mt. Kilimanjaro in Tanzania – the tallest peak in Africa and the highest freestanding mountain in the world.
  • Running my own, self-directed marathon in Warsaw, Poland.
  • Climbing Mt. Elbrus, Europe’s highest peak in the Caucus Mountain Range along the border of Russia and Georgia.
  • Arriving home in Portland hours before I’m scheduled to be in a friend’s wedding party (crossing my fingers for no flight delays!)

That’s 14 flights, 8 bus rides, 2 mountains, 2 marathons, and a wedding.

To say the least, I’m extremely excited but more than a bit nervous to set out on such an ambitious adventure on what most would consider a pretty condensed schedule – the whole trip is only a month long!

If that all sounds complicated and/or overwhelming, I can confirm it was a fair amount of work to put together, but it doesn’t actually have to be that hard. Over the last month, I’d estimate I’ve spent around 10 – 15 minutes a day putting the plans together. When you look at it like that, it becomes a much more manageable task.

Maybe you don’t have any desire to climb mountains or run marathons like I do, but if you’ve ever thought it would be fun to take a trip across the globe and have some unique experiences along the way, I don’t think you should let complication get in the way of your fun. It doesn’t have to be complicated, and once you know some of the basic strategies for organizing a trip like this, figuring out the details is usually just a few minutes a day of focused planning.

Here’s an 8-minute video I made to give you an overview of the tools I’m using to plan and organize this particular trip. The rest of this piece is dedicated to the details of planning a big, international adventure:

You probably noticed that I use one single spreadsheet to manage 99% of my trip. I call it the “command center” and it’s extremely useful for keeping my trip’s most important info in one place where it can easily be referenced.

Now, let’s take a more detailed look at what you’ll need to think about and organize before you embark on your life-altering adventure. The main topics you’ll need to consider are budget, air travel, ground travel, lodging, and health and safety. In some cases, you may need to hire a tour guide for certain portions of your trip and, if you plan to work while you’re abroad, then maintaining an internet connection will also be important. We’ll go over each of these in detail.

Anti-Budgeting for an Awesome Trip

Let me start by saying that I don’t think your budget should be the most important part of the process. Some Most things in life are more important than money and if you’ve been dreaming of taking a big trip or doing something remarkable for a long time, then you shouldn’t let a big bill stand in your way.  However, most of us aren’t independently wealthy yet, so knowing how much your adventure is going to cost before you head out is a valid concern.

I also advocate using a different style of budgeting for a trip like this than most people typically use. Rather than picking an arbitrary number and deciding not to spend more, I’d encourage you to piece together your trip first to get an estimation of how much it’ll cost, and then commit to paying that much for the experience.

The reason I say that is because picking an arbitrary number usually means you’ll underestimate the cost and end up cutting out important parts of the trip in order to stick to your original budget. That comes with a lot of uncomfortable and unnecessary justifications where you tell yourself it’s okay to skip something because you want to save money.

Personally, I’d rather figure out how much it’ll cost, and then simply commit to part with that much money to have an experience that will change my life.

In my case, I’ve committed $8,000 to this trip and I work a little bit every day to find ways to shave that price down. Right now, it looks like I’ll probably get by on closer to $6,000. Admittedly, that’s quite expensive for most people, but don’t let that number scare you – about 75% of that is tied to the(mostly) unavoidable costs of my guided climbs and the remote marathon. If your ambitions don’t lead you to the tops of mountains or out into the African Bush, you can probably get by on considerably less.

Budgeting Tools

I use Google Docs to keep a rough budget. You can see from mine that I’ve priced out two different scenarios and I also keep a running tab of what I’ve already spent:

Since I always purchase everything with credit cards (for the frequent flyer miles we’ll talk about next), I like to make sure I’m keeping up with my budget by having the money I need set aside before I make any big purchases.

I do this by keeping a separate savings account with ING Direct specifically for my travel costs…

…and monitoring my progress funding it and tracking expenses with Mint:

Air Travel

Depending on where you want to go, how you want to get there, and whether or not you’re willing to do a little legwork to save a lot of money will dictate how you decide to travel.

Frequent Flyer Miles

For most people, simply buying the plane tickets to get from place to place on your big adventure will be the most expensive part of your whole trip. I find that to be a bit of a bummer, so I prefer to travel with frequent flyer miles that I pay either very little or absolutely nothing to obtain.

If you decide to go this route, it can help you save a lot of money (often you’ll pay nothing but taxes on your flights), but it can be a bit of a hassle learning the ropes.

The first thing to know is that it’s typically a good idea to become a member with every frequent flyer program you can (they’re free to join). You don’t need to pay attention to all of them, just sign up for each airline’s email updates so you’ll know when they have opportunities to earn easy/free miles. Here are links to some of the most popular programs:

I use Award Wallet, a free web service, to keep track of all the miles I have in different accounts. As you can see, it makes it much faster and easier to plan award travel. I used Dividend Miles from my US Airways account to book most of this trip:


Using Credit Cards to Earn Miles Fast

Using credit cards won’t be the right answer for everyone, but if you’re responsible with your credit, then it’s definitely one of the best and fastest ways to accumulate points if you’d like to travel sooner rather than later due to their often large sign-up bonuses.

Personally, I’ve used credit card bonuses to earn about 335,000 miles in just the last few months.

Credit card offers vary on darn near a daily basis, so you’ll need to keep up with them to know that you’re getting the best deal (or even a valid one), but here are a few of the most popular airline cards that frequent travelers like to pick up:

To keep up with the best offers and to get all the knowledge you could ever want about frequent flyer miles and air travel in general, you’ll want to monitor the Flyer Talk forums – specifically the Miles and Points sub-forum.

Note: My favorite card for accumulating miles is the Starwood Preferred Guest Amex Card. It’s not an airline card, but it allows you to transfer your points to nearly all the major airlines witha 5,000 point bonus for ever 20,000 miles transferred. While I’ll eventually cancel most of my airline cards, this one will stay in my wallet.

Keep in mind that many frequent flyer credit cards come with an annual fee. In most cases, the fee is waived for the first year and you can avoid it altogether by canceling before the renewal date. In some cases, the bank that issues the card will offer some sort of reward for not canceling – a “retention bonus.” This isn’t always the case, but it’s worth asking about.

Another thing to remember when you’re stockpiling frequent flyer miles through credit card offers is that you’ll normally have to meet some type of spending limit. These vary greatly, but are usually along the lines of “spend xxx in xxx months in order to receive the sign-up bonus” types of offers.

Now, I’m incredibly frugal, so meeting the spending requirements with my normal day-to-day purchases is nearly impossible. The way I get around this is by purchasing $1 coins from the U.S. Mint. Since I started doing this in 2009, the rules have changed considerably, and some banks will no longer credit you with points if you use this strategy, but in my case, it still works quite well and every two weeks a box of money shows up at my doorstep that I use to pay a few bills and deposit the rest in the bank. The net effect is, of course, a bunch of free points.

Concerns About Your Credit Score

One last thing to keep in mind is that applying for a lot of new cards can have a negative effect on your credit score. Since I’m currently in the middle of obtaining a lot of new cards (and a hell of a lot of frequent flyer miles!), I watch my credit closely using the free credit monitoring site, Credit Karma.

From the screenshot below, you can see that my score actually increased when I first started adding cards, but as I added even more, it’s started to decrease slightly:

This is mostly because the average age of my credit file is becoming very young as I apply for more and more cards. I’m not too concerned about this since I’ll be dumping most of the cards that I’ve acquired before the annual fee comes due, which will positively affect my score (the average age of your credit file is more important than the few points you lose by closing a card).

Also, I have no major purchases to make in the near future where my credit score will come into play, so I don’t anticipate any negative effect from this credit campaign, but if you do, it’s at least worth noting.

To keep track of all these new cards, I have a spreadsheet that tells me  when I applied, when I received the card, what the bonus is, whether it’s posted to my account, and when I need to cancel by:

I also create events in my Google Calendar that remind me a few weeks before each deadline so I don’t forget to cancel a card and end up paying a renewal fee.

Using Your Miles the Smart Way

One of the most valuable lessons I learned on my frequent flyer mile quest is about airline partnerships. If you have miles with one airline, but it doesn’t fly where you need to go, it’s likely you’ll be able to use your miles to book an award on any of their partner airlines that do fly there. That’s really valuable.

The three major airline alliances are One World, Star Alliance,  and Sky Team. Personally, I try to target most of my earnings around American Airlines (One World) and U.S. Airways (Star Alliance). This allows me to go nearly anywhere in the world by using one of those two airlines to book an award ticket through one of their alliance partners.

For instance, neither U.S. Airways nor American fly to any of the airports that I’m going to on this upcoming trip, but since they’re both part of bigger alliances, I was able to use my miles in those accounts to book travel with United, South African, British Airways, Lufthansa, and Lot Polish to get to where I needed.

Another incredibly valuable thing to know about award tickets is that they often allow you to book a stopover or open-jaw segment on your itinerary at no extra cost. A stop-over lets you stay (usually up to a year) at one connecting point on your trip, and an open-jaw allows you to stop at one place and continue on from another.

For this upcoming trip, I used the stopover strategy to basically get a free ticket to Europe by routing my flight home from Johannesburg through Warsaw, Poland where I have a 14-day stopover that will allow me to transit to Russia, climb Mt. Elbrus, and return to Warsaw before continuing home. Pretty handy!

Side note: While trying to book a separate award ticket from Johannesburg to Nairobi, Kenya, the American Airlines rep told me the only possible award routing between the two cities required a layover in London! When I laughed and told him I didn’t have time for a stopover 2 continents away, he just sighed and said, “I don’t make the rules.”

Unfortunately, I don’t have time on this trip for an extra stay in London, but maybe you do? These weird routings seem to exist all over the place. Do a little digging and ask around before you book your next award ticket, and you just might get a second, unexpected vacation out of it!

My friend, Steve, is using these strategies right now to get to 4 continents and 10 countries for a whopping grand total of $418.

A Few Other Tools

One tool that’s very handy for finding valid routings is Award Nexus. It just came out of beta and is a bit clunky, but it’s an invaluable tool for quickly finding available award routings on most major airlines.

When I’m not sure if I should redeem miles for a flight or just pay for it, I like to use Kayak or Skyscanner to quickly price check. A good rule of thumb is to value your miles at about $0.01 per mile (meaning you shouldn’t pay more than that to accumulate new miles). If you plan on going to lots of expensive places though, you can get away with valuing them a little higher.

World Airport Codes is, in my opinion, the best place on the Internet to quickly find airports and airport data around the world as well as the distance between airports.

Chris Guillebeau’s Frequent Flyer Master is the most comprehensive guide I know of on getting and using frequent flyer miles (and I am happily an affiliate for it).

A warning on budget carriers: Ryanair and other budget carriers like it can be great deals – I’ve scored free and incredibly cheap tickets with them before – but to make it worthwhile you need to be traveling light (they charge for every checked bag and overweight fees are extreme), have plenty of time and access to cheap transportation (they typically fly to out-of-the-way airports far from the city center), and have no need for comfort (the planes are not comfortable and even a bag of peanuts will cost you dearly). That said, if you’re careful, you can get a hell of a deal.

Ground Travel

I prefer to travel primarily by plane, but, of course, air travel isn’t always available when you’re headed to remote locations, so you might need to hire a train, bus, or private transport if you’re headed into the boondocks. Besides, knowing how to get around in a foreign city or even just how to get from the airport into the city center is valuable because there are usually at least a few options and knowing which is best can save you a significant amount of money and/or time.

Trains & Buses

Most ground travel options are, of course, only local or regional, so it’s sometimes difficult to find good information about them online before you leave. One resource I’ve found to be quite useful for shaking down ground travel options is wikitravel.org. Just like Wikipedia, it’s a user-maintained reference guide, and it’s filled with pertinent travel info for tens of thousands of destinations. It’s been invaluable in putting together my upcoming adventure.

If you’re looking for a luxury experience, there’s a service, World Airport Transfers, that will arrange all of your travel from the airport to your hotel at many major airports throughout the world.

Usually, arranging short ground transit is not something you need to worry about before you show up – just knowing your options when you arrive so that you can pick the best one is sufficient. However, occasionally you’ll need to take a longer ground trip on, say, an overnight train or a very long bus ride. If it’s a popular route, then it may be possible to book your ticket ahead of time online. The main problem, of course, is that the online booking system is rarely in English.

My preferred method to deal with this is to use the Google translator plug-in for the Chrome browser. The translations are always a little awkward and confusing, but you can usually get enough context to get through the order process and be sure that your travel plans are secured. Here it is in action on a Swedish train site (not half bad!):

This came in handy a few years ago when I needed to book overland train tickets in Sweden and France. Taking an overnight train can also be a good strategy to save money on a night of lodging, though it’s unlikely to be as comfortable!

Taxis

If you don’t want to end up like I did in Italy – paying $50 for what amounted to a five block taxi ride – then remember this little piece of advice: cab fares should always be agreed upon before you embark.

My $50 blunder was caused by a few mistakes on my part:

  1. We flew Ryanair to an inconvenient airport outside of Rome where mass transit options were limited to begin with.
  2. We arrived late at night after the bus system was shut down. Taxi service was the only transportation available.
  3. I didn’t ask how much the fare was before I got in, even though there were lots of other taxis around.
  4. I hadn’t done my homework and researched how far our hotel was from the airport. Turns out, it was only a few blocks away. Whoops.

Throughout much of the world, cab fares are not fixed like they are in many developed nations. Even when they are, it’s not entirely unusual for a cab driver to try to squeeze a little (or a lot) extra out of an unsuspecting tourist. Use Wikitravel to determine how things work at each destination you’re headed to, know where you need to go, and always agree on the fare before you leave because it’s no use arguing after you’ve already arrived.

In most major cities, taxis are easy to come by, so if you feel like you’re getting the run-around, just say “thanks” and look for another one.

It’s also good to realize that, as a traveler, things will occasionally go wrong and that it’s just part of the experience. I paid $50 for a 5-block cab ride. I wasn’t too happy about it, but I didn’t let it ruin my trip and now it’s just a funny story.

Lodging

After airfare, lodging and hotel accommodations will probably be the second most expensive part of your trip. If you’re up for a bit of a rugged adventure though, that doesn’t actually have to be the case.

Hostels

The easiest and most obvious way to experience the world without paying hotel rates is to stay in hostels instead. The image that conjures up for a lot of people – noisy, dirty rooms crowded with 20-somethings partying all night – isn’t a valid stereotype anymore. Some hostels are more party-oriented than others, but throughout the world you can find clean, quiet, and even private rooms in hostels for a fraction of the price of a comparable hotel.

While I was in Rome a few years ago, my girlfriend and I stayed in a hostel outside of town that was in a converted convent. We paid about $25 a night to stay in a huge, private room with it’s own bathroom. I should also mention it was across the street from the Mediterranean Sea; we could roll up the shades in the morning and pick out our spot on the beach.

My friend, Jenny, put together a good tutorial on how to find great hostels on the road. You can get started with your search by browsing on Hostels.com, Hostel World, or Hostel Bookers.

Side note: There’s some debate over whether or not buying a membership with Hostelling International is worth the cover charge. My opinion is that, at about $30/year, why not? If you’re planning to travel mostly in the US, Europe, or other highly developed areas of the world, the benefits are worth much more than the membership.

Couch Surfing

Couch surfing seems to get an even worse rap than hostels with inexperienced travelers but I can say, without a doubt, it’s my favorite way to travel (and I suspect most people who give it a chance will feel the same way). I couch surfed all across Western Europe in 2008 and I plan to do it again on this upcoming trip because it allows me an experience with local people that I can’t get staying alone in a hotel or hostel. I appreciate that. If you don’t like meeting new people, it might not be a good fit for you.

I primarily use Couchsurfing.org (if you sign up and need a friend, just message me), but there are a number of other communities out there that you can also tap into:

To have the best luck finding accommodations with couchsurfing.org , you’ll want to get verified (requires a $25 donation), start participating on the forums for your home town and places where you plan to travel, and host a few travelers in your own home. If you can, go to a few meet-ups in your region so that you can get to know other people and build some friendships through the site before you start looking for hosts for your own adventure.

Sleeping in Airports

I haven’t done it yet myself, but many travelers do every day (sometimes involuntarily when their flights are cancelled!). For my upcoming trip through Africa and Europe, I have several instances where I’ll be arriving late at night and departing early the next morning, so I plan to do a bit of airport slumber as it’ll be either impossible or impractical to find a room for the night.

I’ll be referencing the great Sleeping in Airports site where travelers from around the world share their insights on the best and safest spots to catch a few Zs in airports throughout the world.

If you run into a similar situation on your own adventure, getting into an airport lounge can be a godsend. Some are better than others, but they all offer more secure and comfortable spaces for sleeping than the main terminals. Typically, you’ll either need a business or first class ticket to access an airline lounge, but some will allow you to pay if you only have an economy ticket – could be worth the fee to avoid a very short airport hotel stay.

Potentially hazardous tactic: Most business and first class tickets are fully refundable, so if you find yourself in a pinch and can’t get into the lounge you want, go to the ticket counter and buy the cheapest business class ticket you can find, use it to access the lounge, then return the ticket before the refund window expires (hat tip to Chris Guillebeau for that trick).

Getting Great Deals on Hotels

Of course, sometimes you just want a good night’s rest in a comfortable hotel. Your best bet at finding a good deal in a nice room is probably on Priceline or Hotwire. Personally, I don’t do a lot of messing around with hotels, but there are some pretty smart folks that do over on the Better Bidding forum where you can learn all about how to get the best prices at great hotels all over the planet.

Chris Guillebeau also publishes a travel hacking guide called Travel Ninja that includes a step by step guide on how to “game” the Priceline bidding process to get the lowest prices available.

Generally speaking, the Starwood Amex card and the Hilton Honors card are the best out there for racking up hotel points like you would with frequent flyer miles. Carrying those two cards will get you access to reasonable rates at great hotels throughout most of the world, and Starwood has a points + cash program so that you can still get a good discount even if you don’t have enough points to redeem for your whole stay.

Health & Safety

Here’s one aspect of travel that pretty much everyone worries about but doesn’t always get a lot of attention. It’s a fair concern, but, to be honest, is probably a bigger psychological barrier than a real threat.

Yes, people sometimes get mugged on vacation or fall ill to some weird disease, but unless you’re traipsing naked through the Amazon, the potential risk is not as big as it might seem. Similarly, you’re more likely to die tomorrow in a car accident than you are by going skydiving, but what are people typically more afraid of? We’re scared of the unfamiliar, and adventure travel is usually just that – very unfamiliar.

Don’t Look Like a Tourist

At the same time, there are a few things you can do to significantly reduce your risk, and the number one tactic is to simply try not to look like a tourist. Obvious tourists are easy targets for pick-pockets and scam artists.

When I travel, I like to carry a hidden money belt with my most important documents but never use it in public, keeping my daily money and credit cards in my wallet stored in my back pocket. Fumbling around with a money belt or some type of hidden wallet is one of the fastest ways to broadcast, “Hi, I have no idea what I’m doing. Please come try to take my money.”

You might also consider picking up a few cheap pieces of clothing wherever you go. I love good travel clothes, but they’ll certainly mark you as a tourist if you spend too much time in them, just like carrying around a giant camera and city map will.

Finally, don’t ever exchange currencies with a street peddler offering to help you out. Find a legitimate exchange machine, office, or bank. At best, you’ll get a terrible deal, and, at worst, you’ll get counterfeit money.

You can get lots of region specific travel safety info by visiting Wikitravel.

Disease & Immunizations

If you’re traveling through the developed world, you shouldn’t have to worry too much about weird diseases or getting a bunch of extra vaccinations, but if you plan to wander off the beaten path, it’s probably at least worth looking into.

For my own upcoming trip, I’ll be traveling through the “yellow fever belt” of Africa, so I’ll be required to be vaccinated in order to re-enter South Africa. Malaria will also be a concern, but not a serious threat in the regions that I’ll be visiting.

Most travel health sites recommend a slew of immunizations for me, like:

  • Hepatitis A
  • Hepatitis B
  • Typhoid
  • Rabies
  • Tetanus
  • Polio
  • Measles, Mumps, Rubella

I’ve already been vaccinated for a number of these, but I’ll be checking my health history again before I leave.

The vaccinations you need before gallivanting off will differ depending on what region of the world you’re headed to. Check the CDC’s Travel Health to find out what you need. MD Travel Health and Travel Doctor are good resources too.

Travel Insurance

If you’re in the U.S., you already know how incredibly expensive and convoluted health insurance is, and most policies won’t cover you when you’re overseas. Thankfully, travel insurance is relatively cheap and easy to get. Under normal circumstances, I wouldn’t recommend it, but for a potentially dangerous and expensive adventure, it might be warranted. In my case, Russia requires that I carry insurance to qualify for a visa.

Since I’m required to have insurance when I visit Russia, I purchased mine from World Nomads. They’re probably your best bet if you’re planning anything wild as they cover all kinds of adventure sports. I’ll be glad to know that if I fall off Mt. Kilimanjaro, I’ll have someone to put a band-aid on me (but only if I fall from below 15,000 feet; read the fine print!).

What is and isn’t covered varies depending on where you’re from and what you’re doing, so read the fine print to make sure what you’re planning to do is covered. A few other travel insurance sites to check out are:

Remember: If you’re a Hostelling International member, you already have some limited coverage. Best to make sure you’re not doubling up unnecessarily.

Hiring Tour Guides the Smart Way

In 99% of cases, I’d typically say that hiring a tour guide is a waste of money and a loss of an authentic experience – most people are completely capable of putting their own adventures together and will have more fun anyway – but sometimes it is necessary and in some cases unavoidable.

In my case, I’m paying a tour company a lot of money so that I can run in the Big 5 Marathon in South Africa. Could I have that same experience without hiring anyone to put it together? Maybe, but I’d probably get trampled by an elephant. There are a lot of logistical issues to consider with an adventure like that, so I’m happy to pay someone to make sure I don’t get eaten by a lion while I’m running or get lost, have a heart attack and be picked over by vultures.

In Tanzania, it’s actually against the law to climb Mt. Kilimanjaro without hiring a guide. It’s an economic concern that ensures the people of the region have jobs and a bunch of tourists don’t just come and trash their mountain without at least paying for it.

If you find yourself in a similar situation, there are a few things you can do to make sure you pick the right contractor.

  • Search for reviews on Trip Advisor. If it’s travel related and costs money, someone (or many people) probably has an opinion about it and Trip Advisor is an excellent way to find it. I narrowly avoided one Kilimanjaro guide after finding a ton of bad reviews about them.
  • Check Internet forums. If you’re hiring someone to guide you on a specific activity like I am, you can usually find more candid reviews in the forums where people hang out to talk about that specific topic.
  • Create a comparison matrix. I learned how to do this when I worked in construction and had to evaluate bids from sub-contractors. If you’re courting a few different guides, make a chart so that you can easily see what is and, more importantly, isn’t included in each outfitter’s price. If it’s not specifically mentioned, don’t assume it’s included – you need to ask.
  • Trust your first impression. If you don’t like how you were treated on the very first contact you made, don’t anticipate that things will get better in the future. Move on to the next one.
  • When possible, go local. This is sometimes difficult to do when there’s a considerable language barrier, but most large tour operators simply hire out to local guides. You might save a fair bit if you’re willing to do the legwork to cut out the middle man.

Working Abroad & Living in the Cloud

When I tell people about my plans to climb mountains and run marathons all over the globe, one question always comes up:

“How will you pay for it?”

It’s a reasonable question since I’ll be away from home for a long time and my adventures, despite all I do to reduce costs, are still a significant investment.

The answer, of course, is that I’ll be working while I’m away. Riskology.co is now a location independent business, so while I’m off exploring, I’ll still be working to maintain the site and perform any necessary business work to keep the cash that funds these adventures flowing.

If you have a traditional job and this all sounds a bit too unrealistic, there are people like Allan Bacon and Sean Ogle who’ve done a great job figuring out how to craft a remote work agreement so you can do this kind of stuff without quitting your job.

Finding WiFi

Once I’m actually abroad, though, I expect that working will be a bit more complicated than just sitting down in front of my computer and typing. For starters, finding reliable internet service will be a little tricky.  I’ll be using coffee shops and internet cafes wherever I can to get some work done. Here are a few websites I’m using to find places to work:

Here’s Lifehacker’s definitive guide to finding free wifi. If you’re feeling mischievous and have low moral standards (or if you’re just desperate), here’s a how-to on sneaking into password protected wifi networks.

But what about when I’m out in the bush or up on a mountain? In case it wasn’t obvious, being able to tweet my victory from the top of a mountain is very important!

For that, I’ll likely be using an unlocked smart phone coupled with a local sim card from the country I’m traveling in. Believe it or not, cellular coverage is becoming prominent in even the most remote corners of the planet. You can even get 3G coverage at the summit of Mt. Everest now.

Working from a cell phone in a tent on a mountain where taking my gloves off could mean losing a finger isn’t exactly the fastest or most ideal set-up, but it’ll work in a pinch and it’ll allow me to keep the gears turning here at Riskology.co for as long as I’m away. That’s useful. In a pinch, you can also tether your cell phone to your notebook, giving you more control by using the phone as a mobile modem.

Warning: If you have high altitude aspirations like me, don’t bring along any devices with traditional hard drives – high altitude will destroy them. Solid state drives only!

Making International Calls

I don’t make phone calls often while I’m at home, so I don’t anticipate making many (or any at all) while I’m away, but if I needed to, it would probably be to reach someone at home, which would be an expensive proposition whether you’re using a sim card from home or from abroad, perhaps even thousands of dollars.

In this case, Google Voice is probably your best bet. Since you can change what numbers your G-Voice account rings to, it’s easy to set it up to receive calls no matter where you are in the world. Remember, if you’re using a local sim card to get affordable cell coverage while traveling, your phone number is going to change every time you change services. Just give people your Google Voice number and they’ll be able to get in touch with you via a local number at home no matter where you are. You can also make very affordable outgoing international calls right from your computer or smartphone using a WiFi connection – likely a lot cheaper than any cell provider offers.

Skype is also an invaluable tool, allowing you an easy way to video chat with anyone in the world for free who has the service, just like you did in high school with MSN Messenger or AOL Messenger. You can also make affordable international phone calls using Skype.

Other Handy Tools

Here are a few other invaluable web-based tools that that make working on the run a lot easier:

  • Drop Box –  A free, web based storage box where you can keep critical files easily accessible if you ever have to switch computers.
  • Drop it to Me – Drop Box is easy to use by yourself, but if you need to let other people upload to it, it’s a little more complicated. Drop it to Me simplifies the process by giving you a unique upload page where anyone can go and upload a file to your Drop Box.
  • Amazon S3 – If you need to store and manage a lot of data, Amazon’s S3 service is an affordable way to do it. If you’re on a Mac, you can even sync Time Machine and S3 to automatically backup your hard drive whenever you’re online. No more external back-up drive.
  • Rescue Time – When you only have a few precious minutes each day to do your most important work between WiFi connections, it’s good to make sure you’re actually getting work done. Rescue Time is a web-based app to help you make sure you don’t waste those few minutes.
  • Outright ­­– This is an app that you can use to manage your accounting. It’s not robust enough to run a multi-million dollar business, but if you run a small operation like me, it’s perfectly capable.

Also keep in mind that if you’re jumping around from country to country, you’ll want to make sure you contact any banks where you have accounts you’ll need access to while you’re away or they’ll get frozen the second you try to make a purchase abroad. This is important whether or not you run a business.

If you deal with PayPal a lot, you’ll want to be sure you’re very specific with them about where you’ll be and when as there are many reports of people having their accounts locked just by signing on in a foreign country.

Bon Voyage

Finally, I want to say that I’m not some guru or travel ninja. I’m just a guy that likes to go on big adventures from time to time and I thought there might be others out there like me. If you’re really into traveling, then here’s a list of other great writers and travelers that you’ll probably be interested in checking out:

Get to know these people. You won’t regret it.

Whether you want to wander to the most remote corners of the earth or just see a few foreign cities you’d always heard nice things about, I hope you found something useful here for your travels. If you did, I’d really appreciate it if you’d share this with your friends on Twitter, Facebook, or StumbleUpon.

Also, be sure to sign up for free updates so you don’t miss any articles like this.

Whatever your ambitions are, make sure you take them seriously and follow through. If you get overwhelmed, remember that you don’t need to know everything to have a successful adventure. In fact, if you did, it wouldn’t be much of an adventure at all.

Spend a few minutes every day plotting your course and, before long, you’ll be off on your own magical mystery tour.

Maybe I’ll see you on a bus somewhere.

Can you think of any other travel tips worth noting? Share them in the comments for future visitors and make this an even better travel resource.

Update: Due to popular demand, you can now download this guide along with important updates as a digital guide in PDF format. To get your free copy, just go over here.

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Photo by: Chuck “Caveman” Coker