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The Latest in Travel Hacking

This is a story that involves a) a frustrating series of calls to Expedia, b) a way to repay Expedia's unhelpfulness by giving many of you $200, c) my attempts to order a total of $16,500 coins from the U.S. Mint, d) a Lasik eye exam in pursuit of Delta SkyMiles, and much more.

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What Is First Class Travel Really Like?

Rerouted-Stream The flight attendant escorts me to my seat in 2B. She waits as I put my things down, and offers to hang my jacket. I spread out my books, journal, and iPod over the seat next to me, because I already know the front cabin is half-full and they’ve blocked the seat next to me at my request.

Not that I need the room – the seat is huge. It reclines fully flat so that I can go to sleep after the five-course meal.

As I’m getting settled, another flight attendant comes by with a tray of orange juice, champagne, and water. If I hesitate, he’ll ask, “Would you prefer a mimosa, or maybe club soda with lime?”

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Rerouting Travel Plans

Rerouted-Stream

It’s not technically last-minute – I’ve changed full itineraries right up to the day of departure before – but two weeks before I was scheduled to fly to Ethiopia, I decided to change directions and go to Southeast Asia instead. In fact, I’m leaving this morning! Yikes – after I write this, I really should think about packing.

This post will explain both the why and how of this decision. The why part covers the details of why I no longer wanted to take the trip I originally planned. The how part deals with Travel Hacking – in this case, how I was able to change the entire trip on short notice using Awards tickets and so on.

Take your pick – feel free to read both or either parts depending on your interest level.

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Advanced Travel Planning: Looking Ahead to January-June 2009

Regular Readers: Please fill out my short feedback survey. Thanks to those who have done so already! (If you’re new, just keep reading the new post below.)

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Some of you have noted that I haven’t published any first-person travel adventures lately. I haven’t been to any crazy countries, slept in airports, crash-landed without a visa, etc.

Don’t worry – I’m not getting soft. I’ve enjoyed hanging out in Seattle, trying to make a living, get my book contract sorted out, and recover from a running injury that has bothered me for a while. The extended break has been good for me, but in January I’ll resume my adventures around the world.

Over the past couple of weeks, I’ve been planning out my trips for the first half of 2009. I tend to change things around a fair amount, but as of now, here is what I expect it to look like from January to June. If it seems overwhelming, first remember that I’ve done this a lot – I certainly didn’t begin with itineraries as complex as the ones I’ll show you here.

And of course, I’ll chronicle each trip in more detail as it gets closer. Cool?

JANUARY

In January, I’ll head to Northeast Africa, flying in to Ethiopia, then heading up to Somaliand (not Somalia; even I am not that crazy), over to Djibouti, and hopefully on to Eritrea and back out after about 12 days of roaming.

My fingers are crossed on this one, because the Eritrean embassy in D.C. has not yet given me a visa. If I don’t get one, I’ll have to scramble to figure something else out, because I already have a flight booked out of Asmara, the capital.

Earlier this summer, I learned that the Kurdish (Iraqi) government checked out this web site before deciding to issue me a visa at no charge. They even sent me a “Welcome Chris Guillebeau!” message which made me feel like a minor celebrity, at least in Kurdistan. Perhaps the Eritreans will be similarly kind – guys, if you’re reading this, please help me out. You can keep the $40 money order that I sent; I just need the visa.

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Southern Africa MapLATE FEBRUARY- EARLY MARCH

Assuming I get to Eritrea or at least get home somehow, in late February, I’ll head to Washington, D.C. for a conference, then fly out from there to Qatar to resume the Round-the-World ticket I began last year. That trip will take me to southern Africa – specifically Mauritius and Namibia. I also hope to take a side-trip to Swaziland and Mozambique while I’m over in that part of the world.

After I’m done there, the ticket takes me back to my usual Asian hub of Hong Kong, where I’ll need to figure out how to get back to the States for another four-week stay at home.

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The Three Mysterious CountriesAPRIL

One month later, I’ll be back on the road to visit Haiti and what I call the “three mysterious countries” of South America. They are Guyana, Suriname, and French Guiana. If you haven’t heard much about them, don’t feel bad – that’s why I call them “mysterious.” I’m not sure I’ll solve any mysteries, but I’ll try to at least get there and back.

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south-america-mapMAY AND JUNE

In May and June, I hope to wrap up the rest of South America, which for me includes Peru, Ecuador, Columbia, and Bolivia. I’m not sure I’ll get to all of them, but it would be significant to complete the whole continent, so I’ll give it a try.

Finally (are you getting tired of this?), I’ll travel to Jordan and then perhaps on to the Sudan. I say “perhaps” because Khartoum (KRT) is part of my current Round-the-World ticket, but I suspect it will be extremely difficult to get the visa. I hope I’m not disappointing anyone with this, but Sudan is not a place I am willing to attempt to fly to without a visa. As previously mentioned, I may be crazy but not that crazy.

If I don’t think it will work out a couple of weeks prior to departure, I’ll pay $150 to change the ticket – not really my preferred option, but also not the end of the world. If I have to drop Khartoum for now, I still have a couple of other options in that region that are less problematic for U.S. passport holders.

Planned Itineraries

For those who like these things, the itineraries for the trips are listed below. The parentheses are for transit stops, and the “x” refers to an overland segment.

Northeast Africa

SEA-(PDX)-(FRA)-ADD-xASM-(FRA)-SEA

By extreme travel standards, this is a fairly straightforward trip – all on Lufthansa, and the only complicated part will be the overland journey from Ethiopia (ADD) to Eritrea (ASM), assuming I get the visa sorted out. I also need to get to Djibiouti or Somaliland during the two weeks I’ll be away – preferably both, but nothing is for certain yet.

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Mysterious Countries

The next trip looks like this:

SEA-JFK-PAP-MIA-POS-???-POS-MIA-SEA

The ??? in this one is due to the fact that I’ll need to fly to one of the three mysterious countries (again: Guyana, Suriname, and French Guiana) and I don’t have that ticket yet. PAP is Port Au Prince, Haiti; and POS is Port of Spain, Trinidad – the jumping-off point to get to Guyana or Suriname.

(By the way, you can use this tool to find out what any particular airport code refers to, and the mileage calculator from the same site is also useful.)

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South America

The trip to Bolivia and elsewhere looks like this, tentatively:

SEA-(ORD)-MIA-LBP-LIM-BOG-(SCL)-GYE-(JFK)-(AMM)-KRT

Here I will be resuming last year’s Round-the-World ticket from Miami (MIA). I’ll need to buy separate tickets to and from Seattle, but that’s how I break up my trips to only be away from home for about two weeks at a time.

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A Colorful Array of MoneyHow Much Does All of this Cost?

I could go on about the flights for a while, but hopefully the above information gives you a good overview. If you have specific questions, post them in the comments and I’ll respond. For now, I’ll address the most frequently asked question I get about these kinds of trips: how much does it cost?

First, read this about priorities and how it all started. I don’t own a car, I have no debt, I didn’t take out a sub-prime mortgage when you could get one at 7-11, I spend about $150 a year on clothes, and so on. I honestly believe that most people (at least, those in Western countries who read this blog) who want to travel can find a way to do so. It may require you to make changes or sacrifices, but inertia is a much greater hindrance for most of us than lack of money.

That said, it does cost money to do this kind of thing, so it's only fair to give you the specifics.

Ethiopia & Beyond

I used Star Alliance Frequent Flyer miles for the first Africa trip, round-trip from Seattle. It took a big hit to my United balance (120,000), and I now have only 60k left. On the bright side, I got the flights I wanted, it’s in Business Class (important to me for long-haul and back-to-back overnight flights), and it would otherwise be fairly expensive to purchase a ticket to that part of Africa. The taxes were also cheap -- just under $150.

Cost: 120k Miles + $150 in taxes
Countries: Ethopia, Eritrea (hopefully), and presumably a side trip to at least one additional country in the region

Qatar & Beyond

My Qatar Airways ticket, another Frequent Flyer award, was 90,000 miles and $391 in taxes – and I’m also trying to add a free stopover to Yemen or Kuwait.

I didn’t have any Qatar Airways miles (I’ve only flown with them once, and I credited it to United), so I transferred points from American Express Membership Rewards into ANA Airlines (Japan) to book the partner award. It sounds a bit convoluted, I know, but it wasn’t that difficult in practice.

Cost: 90k AmEx Points + $399 in taxes
Countries: Qatar to resume another ticket, Yemen or Kuwait (side trip)

All of the South America stops, as well as the second trip to Africa (Mauritius, Namibia, Jo’burg, etc.) are part of my OneWorld Round-the-Word trip. This will also take me on to Hong Kong at some point in the early summer. That ticket was about $5,000, and I’ve received tremendous value from it. I have no idea how much it would cost if I were to try to book everything with round-trip flights – certainly several times more than what I pay when I effectively buy the flights in book with the RTW ticket.

Cost: Roughly $350 per country, prepaid last year
Countries: Mauritius, Namibia, South Africa, Hong Kong, U.K. (transit only)

The only “cash money” flights I need to sort out now are the entry and exit flights to the three mysterious countries, the flights within Northeast Africa, and the occasional cross-country trek to Miami or New York. Those will probably be a few hundred dollars each.

Cost: Variable, but usually $200-400 each
Countries: None, but allows me to come home and take side trips

After I complete all the trips mentioned above, I’ll start running out of prepaid flights, so I hope to begin at least one more Round-the-World ticket in the early summer. This one may be back on Star Alliance since I've earned more than 200,000 miles with OneWorld in 2008, and therefore don’t need to worry about elite status with them for a while.

I'm not 100% sure of what I'll do about the ticket, but whenever I sort it out, I’ll let you know exactly what I decide and what the next monster itinerary will be.

Well, You Asked for It

One request I’ve heard several times now is for more detailed travel planning notes. I have a question for you in return: is this progress? Is this the kind of thing that you guys want to know?

I cover even more travel planning details in the original Discount Airfare Guide, and I’ll be coming out with a more advanced Travel Ninja report soon… but I’m also happy to post information like this on the site whenever it seems like a good fit. As long as you give me good feedback, I’ll keep doing it.

Also, remember that next month we’ll look at my version of lifestyle design and annual planning. This includes travel planning, but also creating a structure for work, fun, learning, and more. I always look forward to doing the review in December, and this year I’m looking forward to sharing the process with you as well.

If you have any questions or feedback about the 2009 travel plans, simply leave a comment below. Thanks for reading!

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Related Entries:

Travel Hacking in an Unfriendly Enviornment
What I Talk About When I Talk About Travel (a Travel FAQ)
28 Things I Wish I Knew Before I Started Traveling
Why You Should Quit Your Job and Travel Around the World

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Unconventional Guides:

Working for Yourself: Creating Personal Freedom
Discount Airfare: Surviving Stress and Maximizing Fun

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India Travel Journal Part I

I’m having an Indian coffee in the Churchgate section of Mumbai, roughly 15 hours after my arrival here. Since then, I’ve come in from the airport, crashed at a sad hotel, changed hotels, changed money, and tried to begin the process of acclimation to a culture that is new to me. Mumbai is not a…

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A Short Narration of My Travels So Far

In September 2006 I first considered the idea of trying to visit every country in the world, and I decided to write a short essay about everywhere I’ve been so far. Over the next year I’ll be posting one of the essays each week until I catch up. The compilation below is a short summary…

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Under the Unseen Blue Sky in Sydney, Australia

If you’re going through a dark night of the soul, you might as well pass the time in a beautiful place.

That’s what I was thinking as my hour-long Qantas flight from Melbourne began its descent to Sydney. Australia has long been a place of joy and peace for me, and Sydney in particular. Ever since I first stumbled into town five years ago, when I was denied boarding on a flight from Brisbane to Nauru (long story), I’ve been coming back every chance I get.

This time felt different because, well, I’m different. I’ve been judging the days on a 1-10 scale, and I get excited—at least moderately so—when I feel higher than a 3.

And so as the flight lands in Sydney and I take the airport train to the city, bracing myself against an onset of anxiety, I begin my self-talk.

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Welcome, New Readers! What The Art of Non-Conformity Is All About

37847813471_2cfc03e1df_z I’ve had a lot of new people join my blog recently, mostly from all the media coverage about my new book. Welcome!

If you’re just joining, here’s a quick explanation of what all of this is about. I started this blog wayyyyy back in 2008. My mission is to help people live unconventional lives, especially through self-employment and travel, but also the general theme of non-conformity.

At the time I started, I was pursuing a big quest to visit every country in the world by my 35th birthday. I achieved that goal and wrote a book about it called The Happiness of Pursuit. I also wrote a book called The $100 Startup, and my newest book is SIDE HUSTLE.

But enough about me. What can you find here on the site? A lot of things, but let’s focus on three areas.

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Escape for a Life-Changing Weekend or Build Your Small Business: Two Upcoming Events

As mentioned a few days ago, WDS 2017 is sold out, but you can still register for Academies. These are half-day workshops on a variety of topics, ranging from productivity to wellness and everything in between.

We've noticed that Academies are one of the most popular parts of the WDS experience. You'll learn new skills and make new friends. Oh, and if you're traveling in just for Academies, you won't be the only one—every year there are a lot of folks who make the trek.

--> Check out the lineup and join us in Portland next month!

Whether you're part of WDS or not, here are two other events you should consider attending.

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101 Stories of People with Day Jobs Creating Side Hustles

On January 1, I began a new project: to publish a story every day of someone who starts an income-generating project (a "side hustle") without quitting their day job.

The project failed and I decided to give up. Just kidding! We are relentlessly moving along, publishing story after story—and it's getting better and better!

I recently completed the first 100 days. There's much more to come, but I'm excited about everything I've learned since beginning back in January.

If you're just joining in, you can also catch up on any recent episode from the links below.
Download all episodes from each month:

January | February | March | April

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Couple Uses Southwest Companion Pass to Save $3,800 and Take 14 Free Flights

Link: Southwest Rapid Rewards® Plus Credit Card

I’ve mentioned the Southwest Airlines Companion Pass a couple times over the years. In short, if you’re able to get it—by earning 110,000 qualifying points in a year—a companion of your choice can fly with you for nearly free (just pay the taxes on their ticket) for an entire year.

Here’s a fun story from Annabelle and Christian, two students from last year's Dream Trip course, that have used their Companion Pass to take more than a dozen free flights so far.

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