Advanced Travel Planning: Looking Ahead to January-June 2009

Over the past couple of weeks, I’ve been planning 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, 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?


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.



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.



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.



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 visit 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 possibilities 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


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.


Mysterious Countries

The next trip looks like this:


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.)


South America

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


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.


Money Image by Roby

How 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. In the case of these flights, about 40% are booked with Frequent Flyer Miles and other 40% are part of my Round-the-World tickets, which greatly reduces the overall cost.

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: 4-5 Countries in South America, plus Mauritius, Namibia, South Africa, Hong Kong, and 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!


Image: fun “Dynamic Einstein” Tool

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    • Ted Hessing says:

      Perfect, Chris. The details are stumble-worthy!

      Rest up this holiday season and enjoy the trips next year.

    • Pace says:


      Have you seen this silly animated GIF?

    • Steve Westman says:

      Wow, Chris. That’s going to be a busy few months. I love your site. I’m really envious of your ability to travel as often as you do. Unfortunately at this point in my life I can’t travel as much as I’d like – job, wife, young kids in school. Maybe in a few year when we’re retired.

      Anyway, you talk a lot about the specific details on the flights in your various posts, but you don’t seem to give too many specifics about where you stay and how you get around the various countries. I’d love to hear more details, especially for the lesser know countries. I wouldn’t even know where to start looking for lodging in Ethiopia!

    • Chris says:


      Thanks man! I appreciate the feedback and the Stumble.


      Nope, haven’t seen that one until now.


      Where to stay and how to get around — sure, we’ll do that in another post. I usually say where I end up in each individual trip report, but I can give some general info too. Thanks!

    • CM Burns says:

      Wow! I’m green with envy – that’s quite a year you have planned. I’m anxious to see how the Eritera trip turns out as it’s one of the countries I had planned on hitting this year.

      I’m jealous of your seemingly bottomless pool of Frequent Flyer miles. Wondering if you could hip us to how you continue to accumulate them.

      When you get to Ethopia be sure to visit The Chapel of the Tablet – near the Church of Our Lady St. Mary of Zion in Axum. They claim to hold the Lost Ark of the Covenant in their church!

    • Adrienne says:

      Hi Chris,

      The cheap flight info is very informative and quite alluring. But since I have no hope of taking advantage of a roud-the-world trip which would use up my vacation days in a heartbeat, I’m actually far more interested in the places you actually go. I know for many of them you are in and out, but I love the posts where you actually describe what it was like being in each country.

    • Chris says:


      Well, I wish the supply was bottomless. I do have about 500k in miles right now, but with all the travel and the fact that most of my Awards require around 100k, I am definitely careful about using them only for high-value trips that would otherwise cost a lot in cash.

      I have a lot more to say about FF Miles than I could write in a comment box, or even a full post — but in short:

      1) As mentioned, this year I received 200k with AA (and OneWorld) just due to all the RTW flights. I’m now on the highest level of their elite program, so I get double mileage for most flights.

      2) I also get a lot (easily 80k a year, lately even more) of points through various bonuses, online offers, and even random things like the hair-loss consultation I wrote about recently. I’m planning to create an ebook at some point with more details about how that works.

      3) Finally, credit card spending and sign-up bonuses help. I have received 50k in bonus miles (and 25k in hotel points) over the past couple months alone for accepting new credit cards. This is not something everyone should do, of course, but since I value the miles quite highly, it works for me.

      Make sense? That’s a short synopsis, anyway.


      Yeah, I realize not everyone can do the RTW thing. I’m also looking forward to hitting the ground again and visiting some fun places in January.

      Thanks, guys!

    • Jake says:

      Very interesting post, Chris. I’m looking forward to your reports from the upcoming year. I really appreciate the detail.

      I’d be interested in hearing a rundown of what you do to earn so many reward points.

    • Michal Mitrega says:

      I’ll be in Lima from 12 June to 8 Semptember depending on when I pass the exams in school. But this is the worst-case scenario. (:

      So if you get to Lima at the time, just send me an e-mail and I’ll put you up for free.

    • Joel S says:

      I’ve been to the Sudan, and if you really want to get there, you will either have to go through a tour operator, or go to Cairo or Aswan in Egypt first. You can get the visa in one day there, but otherwise, it’s a long and painful process.

      But thanks for the update, your travels sound great.

    • Melissa says:

      Namibia – wow! I’ve always wanted to go to the Skeleton Coast. Will you have a chance to visit there?

      Do you set aside money for traveling within each country, or do you mostly just spend time in your arrival cities?

    • Laya says:

      If you don’t mind me asking, what conference are you doing in DC? And would you consider doing a meetup with your DC area readers?

    • The Global Traveller says:

      Hi Chris

      Once again you are visiting a number of the same countries as I me. I visited several of them in October and have several more lined up in the next few months or so. And yes, Eritrea is one of the places I’m having visa difficulties for as well.

      Have you taken advantage of the currency turmoil to snap up some super low fares from certain countries (South Africa and South Korea are both particularly cheap for oneworld and star alliance RTW tickets at the moment)? More info on Flyer Talk

    • Travel Over 30s says:

      I love your writing style and the fact you are doing different – just saw that guy who is dancing around the world: on a Visa ad no less so hope something like that pays off for you!

      I must admit though I would hate to do a month here, a month there – for me the flights aren’t usually the majority of the cost, its more the time in country, and I live in Australia so I have to fly to start a trip. You don’t from seattle – just driving south will get you all of central/south America.

      Also re visas: I have invariably found it a lot easier to get a visa in adjoining countries rather than at home e.g. its must quicker/easier/cheaper to get Burmese and Vietnamese visas in Thailand than in Australia! In Africa I suspect a bit more bribery would be involved: and that is always easier with cash over a glass of tea looking the guy in the eye.

      So why all the short trips? You’re a writer you can do that anywhere you don’t have to go home for that

    • Chris says:


      Thanks; that’s nice of you. Good luck with your exams.


      Visa in Sudan – I have a friend who will be in Khartoum who is trying to help me get it sorted out. I’m not highly-optimistic about it, but you never know.


      Namibia – I’m not sure what the itinerary there will be. Yes, as much as possible I like to do some traveling within countries. It all depends, though — I do have to make some sacrifices so I can go to more places. My theory is that I can always go back later and spend more time if I miss something important, which I often do.


      It’s a marketing conference. Sure, I’d love to meet you and anyone else in the D.C. area. I’ll be there the weekend of Feb. 20-22 — just send me a note sometime.

      @Global Traveler,

      One of these trips we’re sure to connect! Yes, I’ve been watching the fares for ICN and JNB/CPT with interest. I don’t think I can commit to buying a new one right now, which is unfortunate, but hopefully the prices won’t be much higher in a few months. Of course, nothing is guaranteed.

      (Everyone else, Global Traveler heads out on the road much more than me, and is also an experienced RTW planner. Check out his blog for more insights.)

      @Travel Over 30s,

      Thanks for the kind words. I’m not a good dancer, so I’ll have to find another way to sponsorship!

      Visas – well, as you mention, it depends on how long you are in one place. I find it can be stressful to depend on getting a visa in an adjoining country. As for short trips vs. long, well, my view is “to each his own.” What is short for one person may not be for another.


      Have a great weekend! Feel free to post more comments or questions, and I’ll check them on Sunday night.


    • Zuri says:

      Chris, congratulations you have a great Site. I read that you are planning to visit Ecuador next year, I live in the capital city of Quito, so when you arrive it will be a pleasure for me to show you around the city at no cost of course.

      Good luck!

    • Kirsty says:

      I love reading about people’s travel plans and yours are certainly more interesting than most. I’m in Haiti right now and it’s an interesting place. I’ve had a chance to meet a lot of locals and it’s been wonderful so far.

      I look forward to reading about it all!


    • David Masters says:

      I find it really inspiring to read about how you’re living your dreams. Thank you.

      Just wondering, have you ever considered the environmental cost of all the flying that you’re doing? – as an eco-conscious person, I’d find it really helpful if you factored that it too.


    • Chris says:

      @Suri, Kirsty, and @David,

      Thanks! Maybe I’ll see you somewhere.


      Yes, I have thought about it a bit. I don’t think I should avoid flying, since the planes go with or without me — but I did write about it briefly in the travel FAQ and may look at it in more detail in the future.

    • Nomadic Matt says:

      I don’t think i’m crazy enough for ethopia right now but it looks like you are going to a lot of good places. rock on!

    • CM Burns says:

      Hey Chris,

      You probably already know this but it turns out Eritrea is on the state department’s list of current travel warnings – here’s the state department’s link:

      Here’s the reason:

      “The U.S. Department of State warns U.S. citizens of the risks of travel to Eritrea and recommends that U.S. citizens defer travel at this time. The U.S. Embassy in Asmara is currently closed for all public non-emergency services “.

      “Since September 13, the Government of Eritrea has repeatedly, and in violation of the Vienna Convention on Diplomatic Relations, interfered with the unfettered delivery of the U.S. Embassy’s diplomatic pouches. As a result, the Embassy is unable to receive critical supplies and materials necessary, including U.S. passports and other citizenship-related documents, for the conduct of normal operations.”

    • David Masters says:

      Thanks Chris – I found what you said in your FAQ really helpful. I don’t fly a lot (a return flight every 2-3 years), but I feel guilty when I do. I think it’s important to treat flying as a privilege and use other means of transport whenever possible. The same is true of driving, so it was great to hear that you choose to use public transport rather than own a car.

    • Pamela says:

      I am amazed with your travels, Chris! This is a very interesting site. As a new reader, perhaps I have some catching up to do here. I stumbled upon this site yesterday (and I’ll “stumble” this article for you!). However, I am wondering about this “round the world” ticket that you speak of. Is this available to the public to purchase? Where do I get more information on that? Is it in your travel publication? I plan on purchasing your travel publication anyhow, but if it is not in there, I would appreciate a link to more info on the rtw ticket.

      BTW: I call Washington state home too!

    • Chris says:


      Thanks for that. I do visit a number of places that are on the State Dept’s warning list, but of course it’s always good to be aware and as safe as possible. I still haven’t heard anything about the visa situation — I need to call them before another week is over.


      Great to hear from you! Are you in Seattle? We are going to do a meetup here at some point. As for RTW tickets, Friday’s post will be all about that… stay tuned!

    • Pamela says:

      Chris, thanks for the reply. I did find the Alliance site yesterday and checked out the RTW tickets. I still don’t really have the money for that, but I hope to someday! We live over in the desert, Tri-Cities. My husband and I plan to make our first (or I mean “my first”) overseas trip next year to Australia. He has been there a few times, and has family there. My dream is to travel to as many countries as I can, but I would need to spread it out alot, and figure out how to afford it. I am still catching up here, but I find this site very informative. Keep it up!

    • Ezekiel Smithburg says:

      what i’m most curious about is what you’ll average for costs within each of those countries, so as to have a better idea of what to expect when going somewhere.

    • Chris says:


      Costs within countries — long story short, I’m not sure. I’ll have to post about that for each trip, because there is considerable variance in each region. My biggest expense is definitely airfare, but of course there are other costs too.

    • jphripjah says:

      Advice for April – Paramaribo, Suriname is crawling with stray dogs. Don’t get bitten.

      Also, I hear that Georgetown, Guyana sucks but the interior of the country is nice.

      Machu Picchu is definitely worth it. You can take the train in and then do day hikes around the ruins. Inca Trail isn’t necessary at all.

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