The Monster Trip of 2009


Last year at about this time, I took what I called the Monster Trip of 2008.

It involved four continents, driving through Italy in the middle of the night, visiting Iraqi Kurdistan, roaming by train and bus across the Baltics and Moldova, and finally coming home through Asia – where I mistakenly double-booked myself on two non-refundable tickets home from Japan.

What fun that was. Now it’s time to repeat the process, although with a completely different itinerary, and hopefully without getting stranded on a faraway continent three days before I’m supposed to come home.

Frequent questions I hear about this kind of travel:

Does it get tiring? Yes.

Is it worth it? Absolutely.

Why go to so many places on one trip? 1) that’s how Round-the-World tickets work, and 2) I’ve got less than four years left to achieve the goal.

In other words, don’t worry; I know what I’m doing. Usually.

Goals are funny things: as long as we’ve chosen them well in the beginning, they’ll be worth it in the end, but there will also be some hard times along the way.

Think about Lance and the Tour de France, Obama and the quest for the presidency, etc. The best things in life usually require ups and downs, sacrifice, struggle, et al. We are frequently better off in the end because of the struggle, not in spite of it.

Struggle or otherwise, I have a couple of things working in my favor this time:

First, I’ve improved. I make a lot of mistakes, but I don’t like to make the same mistake twice. The nice thing about travel is that the more you wander, the more experienced you become. These days, it doesn’t take me long to settle in anywhere.

I’m also a better writer and have learned more about what I can and can’t do. A friend of mine likes to say, “If at first you don’t succeed, destroy all evidence that you’ve tried” – but I’ve kept the evidence in the archives for transparency’s sake.

Second, more of you are interested, which creates more motivation. Last year I wrote for a small group of about 3,000 people. (Big thanks to everyone who’s been here for a while; I really appreciate you guys sticking around.) Now I have a much larger core group, in addition to another group of passive readers and those who read the syndicated content elsewhere. If I fail to cross a border or get tempted to take it easy somewhere, I can think about the story I’d have to tell.

The Itinerary

When this article is posted, I’ll be flying to La Paz, Bolivia. I made it to my starting point yesterday by flying PDX-ATL-MIA. Over the next 20 days I’ll be in four continents, starting with South America and ending in Asia before coming home.

For those who are airport code savvy, the first part of the trip looks like this:


Persian Gulf – As long as my Saudi visa comes through, I’ll be in Riyadh for a couple of days and Kuwait for a couple of days.

Malaysia – I leave Riyadh for Hong Kong and then hop over to Kuala Lumpur, Malaysia for the final stop of the trip.

The second part of the trip looks like this:


Coming home from Malaysia, I’ll be traveling on my first-ever “mistake fare,” which is interesting enough to be a story all its own. I’ve been looking at mistake fares for years, but never managed to pick one up until I got this one two months ago. At some point during the trip, I’ll post more about how that works and the details of the flight home.

The Cost

Most of this trip is booked on a OneWorld Round-the-World ticket. I’m a huge fan of these tickets due to flexibility and overall economy. Pricing for RTW tickets is determined by country of origin, and this one began in Sri Lanka last fall. Even with taxes, the price per segment was just under $300 each, including all of the long-haul flights to and from continents.

Last spring, OneWorld announced that they would be shifting from a maximum of 20 segments to a maximum of 16. The deadline for getting a 20-segment ticket was June 1, 2008, so I headed up to Vancouver, B.C. on May 31 to pick up my ticket. Even at 16 segments, the tickets are still a good deal – but I didn’t want to pass up the chance to get a 20-segment one while I still could.


My last segment on the RTW ticket was the return flight from Haiti a couple of months ago. From there, I bought a one-way ticket to get home to Portland, and another one-way ticket to return to Miami yesterday.

Most of my domestic flights are booked on American Airlines, because I fly more than 100,000 miles a year on OneWorld and have the highest level of status with them. This time the Delta fare was much lower ($189), so I went with them.

Ironically, I’m a Platinum Elite flyer with Delta even though I rarely travel with any SkyTeam carrier. Last year when Delta began its merger with Northwest, I requested an elite status match with Northwest. The request was approved, so now whenever I fly with either carrier (Delta or Northwest) I’m automatically placed on the upgrade list alongside their most active travelers.

(I write about status matches in the two travel products in the AONC store. At some point I’ll be making a third one that will be a complete guide to Frequent Flyer miles.)

I found more irony in the fact that I was not upgraded coming back from New York last week on the U.S. airline I patronize most often (American), but Delta upgraded me three days prior to this trip on both segments.

I was really happy with the flights yesterday – it’s not like flying long-haul, but Delta’s domestic service certainly beats American’s. I wish SkyTeam had a better Round-the-World product to compete with OneWorld and Star Alliance.

Air Asia to Kuala Lumpur

My OneWorld ticket ends in Hong Kong (at least for now – there are still a couple segments I’ll pick up in late August), but due to the terms of the mistake fare, I had to get to Malaysia to resume my trip home. To do that, I booked a one-way flight on Air Asia, a low-cost carrier based in Kuala Lumpur that I’ve traveled with before. The ticket cost $59.


For a trip like this, I’ll stay in a variety of locations – hostels, guesthouses, hotels, and with friends. In Santiago the hostel is about $24 a night; in Hong Kong it’s about $40. Friends are putting me up in a few places (Bolivia, Peru, Malaysia). I also have several red-eye flights that save me the cost of lodging (MIA-LPB, JFK-AMM, RUH-HKG).

In Riyadh, assuming I get there, and in Kuwait City, I’ll be staying in hotels. Those places are not really known for independent travelers, and I’ll probably be needing a break at that point. In Bogota I’m also staying in a hotel partly because I don’t know much about Columbia and would rather choose a safe option for that country. In addition to the comfort factor on a long trip, staying in hotels from time to time helps me get more work done and catch up with my online life.

The Unknowns

I’ve never been on a major Round-the-World trip where something didn’t go as planned or there weren’t any challenges to overcome. My most obvious challenge at the moment is the visa from Saudi Arabia, which has been promised to me but I’m still waiting for.

Because I never know who’s reading along and I don’t want to jeopardize my chances of getting the visa, I can’t explain the whole story behind why this has taken so long. Suffice it to say that I’m really looking forward to visiting Riyadh, and I will certainly follow the laws and customs of the kingdom while in the country. I’m not a journalist and am mostly just trying to get to Hong Kong on my Cathay Pacific flight a couple of days later.

I’m making a quick trip through NYC in transit to Amman a week from today, and I really hope that my passport (and the visa) will be waiting for me there. If not, I have a couple of options, but none of them are that good – so let’s hope the visa arrives.

The Meetup Schedule

I don’t have any formal meetups planned like we did in NYC last week, but along the way I’ll be visiting friends and readers on a smaller scale. In Malaysia I’m excited about hanging out with Reese Spykerman, my superstar designer and friend, and her husband Jason. Reese and I have worked together virtually for a long time now, but we haven’t met in person yet.

In La Paz, Lima, Bogota, and Santiago I’m meeting with readers who have contacted me recently. Santiago (Chile) is probably the best place to see a small group of people – I’ll be there the night of Thursday, July 2, so if you’re there, let me know.

A lot of folks have written in from Argentina and Brazil asking if I’ll by stopping over in their great countries. Unfortunately, I’m not – I was in Buenos Aires last year and agreed with other opinions that it’s one of the best cities in the world, but I won’t make it there on this trip. See the above notes on sacrifice and the overall goal.

I know there is a Malaysian contingent on my email list, but I don’t know who everyone is or if most of them are in K.L. or elsewhere. If you’re there, feel free to send me a note and we’ll see about setting up something while I’m in town (July 13-15).

Other Updates

I write a monthly newspaper column for the Oregonian and post more detailed travel updates on Yesterday’s column in the paper has more info on the trip and can be read here. I’m also writing occasionally for Anderson Cooper’s 360 site and will let you know when something goes up over there.

Lastly, I post live updates from wherever I am on Twitter every day. If you happen to be in the same place at the same time as me, be sure to say hi from Twitter or send me a note from the site.

I fully expect this to be a tiring adventure, but I also expect it to be fun. Sometimes the two categories go hand-in-hand.

See you next from the road. Wish me luck!


[Travel note: I work from wherever I am in the world, but comment moderation and email response is frequently delayed when I’m traveling.]

La Paz Image by Guillermo

Subscribe now and you’ll get the best posts of all time.


  • John says:


    I have yet to start traveling, but seeing the struggles you have overcome has inspired me to prepare for those same challenges when I commence my travels.

    Good luck on traveling the world.

  • Mike Echlin says:

    Hey Chris – what an exciting journey! Can’t wait to read the updates. Thanks again for sharing.

  • Shannon says:

    So excited for you. I have a personal goal to go somewhere for 1 whole month rather than the typical 1-week vacation. Plan to do that next summer w/my children and live like a local a bit rather than just being the typical tourist. Your amount of traveling sounds crazy fun. I’ll be interested to hear someday where your favorite places were and where you plan to return.

  • Adrian says:

    Chris, how was the AirAsia experience? I’m planning on traveling to Bangkok next year and they have a killer offer from London, for about $800. Thanks!

  • Chris says:

    Thanks, guys! I made it to La Paz this morning and am having fun with a great expat family that is hosting me.


    I like Air Asia just fine – I haven’t done the long-haul with them, but I had two flights in January and was quite happy. If they offer the option on the long-haul, I’d probably pay a bit more for an exit row seat.

  • Laura Cococcia says:

    Awesome – can’t wait to hear about every location. I’ve started to look into the RTW tix based on your recommendation. Love being Exec Plat but that only gets one so far!

  • Adam says:


    Air Asia is fantastic. I’ve flown several times around southeast asia. New jets, clean. If you switch planes in Kuala-Lumpur it can get a little messy, otherwise its a great airline. I’ve met the founder of the airline, Tony Fernandes, he’s quite a character.

  • Etsuko says:


    Glad to hear that you made it to La Paz. I haven’t been there yet and am looking forward to reading your stories.


  • Mike says:

    Looking forward to the posts on this and best of luck with the visa!

  • Rasheed Hooda says:

    Hey Chris,

    Sounds like you’re having a lot of fun. Looking forward to hearing the details as you travel.

    I am looking forward to the day, soon enough I hope, when I will have a “small” readership of 3000 or so. 🙂


  • anwar says:


  • Sean says:


    Really looking forward to getting your thoughts on La Paz. I got an offer from a friend to spend some time working in a hostel down there, and am considering using the opportunity as a starting point on my quest to travel and work for myself. Enjoy the trip!

  • Martin says:

    Rock on.

  • Adrian says:

    Chris, thanks for the reply!

    Adam, what did you mean by “messy”? 🙂 I’m actually planning on spending 1 or 2 nights in Kuala Lumpur as well.

  • Morgan says:

    I hope things go as planned, but your inadvertent adventures (“mistakes”) are definitely entertaining and enlightening, so thanks for being so good-natured about sharing them! Cheers!

  • Karen says:


    You writing and journey is beyond inspiring! I can almost read your airport code lingo… I think I’ll know I’m a true world traveler when I can read it all! I’m living vicariously thru you, reading about your travels. I think it’s so awesome that you are staying with people that read your writing, and are able to stage meet ups. I’m curious to see what happens with your Saudi visa… and hear details about that leg of the trip.


  • Liz says:

    This is an incredible (and ambitious) travel schedule! I’ll be watching for posts, and hoping you get the Saudi visa.

  • Elizabeth says:

    Definitely a whirlwind RTW tour you’ve got planned. Your visa should turn out fine from similar stories I’ve heard; I wonder occasionally whether embassies deliberately like to keep applicants sweating for weeks.

    How long will you be in Hong Kong? I’ll be there twice for a visa run from China/transit to Sydney later this summer.

  • Franisz Ginting says:


    have you tried to go to Indonesia?


  • ieishah says:

    hey chris! i’m in the middle of my own 20 day monster trip. i like to revisit places, learn the language, sample live music, stay in people’s houses and eat all their food… lol!

    i began in paris last week, where i met up with old friends (used to live there) and danced onstage with emir kusturica and the no smoking orchestra at the solidays music festival. crazy, crazy stuff!!

    i’m in montpellier now, heading to london tomorrow (wednesday), and belgrade on friday. from there, my [serbian] boyfriend and i are taking a road trip through rural serbia to macedonia. we’ll spend 4 days in ohrid and skopje, before heading back to serbia, this time novi sad, for the exit festival. it’s the 10 year anniversary so it should be amazing!!

    from there i’ll go back home to barcelona for a week, before flying to new york city (my hometown) where i’ll stay for two months…

    so good luck with your travels!! i’ll be checking in on yours during mine!

    vaya bien…

  • Mark says:


    I’m curious how much luggage you typically take on a trip like this. I went on a 23 day trip through Europe last year, and managed to get by with a small suitcase from Rick Steves’ site, and a backpack.

    I laughed at the people I saw getting on and off planes and trains with multiple huge suitcases per person!

    Next time I am tempted to just take a back pack with a change of pants, a couple changes of shirt, and a couple changes of underwear. They do have laundry machines pretty much everywhere, after all. 🙂

    I also have travel clothing which is easy to wash in a sink and generally dries out pretty quickly, which worked well for me on my trip last year.

    So what tips do you have for the rest of us?



  • Chris says:


    Yes, I’ve been to Indonesia before, but I won’t be going on this trip. I plan to stop off in Bali on the next one, though.


    See this post for my packing list. I’m definitely on the “less is more” side of packing philosophy.

  • Melody says:

    You know how sometimes a person can say something so deceptively simple you almost miss the value of its meaning? Or maybe you overlook it because you hear variations of the assertion throughout your daily life, and it falls into the “familiar” category… You did that for me, here: “The best things in life usually require ups and downs, sacrifice, struggle, et al. We are frequently better off in the end because of the struggle, not in spite of it.” LOVE that! Thanks, as always!

    Living vicariously today…

  • Martin says:

    Definitely looking forward to hearing your stories about the Persian Gulf countries.


  • Shu says:

    Hi Chris,
    I’ve recently started following your site and I’m definitely inspired! I just got to get the doing part right. I’m currently working in Hong Kong. If you’re planning a meetup, let me know!
    Have fun and take care

  • Colin Wright says:

    I’m super-excited for you, Chris!

    Keep producing good stuff and there will always be more of us here, waiting to reading it!

  • Claudia says:

    Hi Chris…hope that you enjoyed your stay in La Paz…I am so happy to hear that you made it to Bolivia (my country) 🙂 Too bad I found out about your trip today because I would have loved to meet you, I check the Art of Nonconformity periodically. I reside in Cochabamba.



  • Tera Wages says:

    Hi Chris,

    My husband, Wes, and I plan on traveling to Europe next summer and spend two months traveling. We are debating renting an apartment in Italy and taking one or two day trips to other cities we want to go. But allowing Italy to be our base. Or we are debating jumping from hostel to hostel. We are traveling with expensive camera gear, and want to be able to keep our equipment as safe as possible, while also keeping the trip reasonably affordable. Do you have any tips for us?


  • Chris says:


    I definitely think the apartment is the way to go in that situation. For two months I don’t think you guys want to jump from hostel to hostel – maybe rent the apartment by the week and then jump around as needed.

    Good luck! Sounds fun.

  • Ariane says:

    Chris, I enjoy your updates. I just finished reading about your adventures in Saudi Arabia. I didn’t know women couldn’t travel there by themselves. Interesting. Anyway, safe travels.

  • fakeidking review says:

    Fantastic beat ! I would like to apprentice while you amend your website, how could i subscribe for a blog website?
    The acxount aided me a applicable deal. I were tiny bit familiar of this your broadcast offered vivid transparent concept

    Look into my web site … fakeidking review

Your comments are welcome! Please be nice and use your real name.

If you have a website, include it in the website field (not in the text of the comment).

Want to see your photo in the comments? Visit to get one.