Huffpost Healthy Living
The Blog

Featuring fresh takes and real-time analysis from HuffPost's signature lineup of contributors

Chris Guillebeau Headshot

The Monster Trip of 2009

Posted: Updated:

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.

2009-07-02-lapazbolivia.jpg

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:

PDX-ATL-MIA-LPB-LIM-BOG-SCL-JFK-AMM

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:

AMM-KWI-AMM-RUH-HKG-KUL

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.

PDX-ATL-MIA

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.

Accommodation

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 everything went 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 OregonLive.com/travel. 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

From Our Partners