(Photo: Norman B. Leventhal Map Center)

Chris Guillebeau travels the world and writes for a small army of remarkable people at The Art of Non-Conformity blog. He is a master of clever air travel (among other things), and this is a guest post on perfecting one of the rare gems that can truly change your life: Round-the-World (RTW) tickets.

Enter Chris…

——

To outsiders, buying a Round-the-World plane ticket is a mysterious process. How does it work? Where can you go? How much does it cost? Unlike buying a simple one-way or round-trip ticket, you don’t just go to Kayak and click the “Everywhere” tab. (You don’t have to look – there is no such thing.)

Over the past three years I’ve spent at least 60 hours, probably more by now, learning the ins and outs of Round-the-World travel. In this post, I’ll explain a) why Round-the-World tickets can be an excellent value even if you’re not trying to visit every country in the world like I am, b) how to plan your trip, c) how much it costs, d) 7 bonus tips on optimization.

The Time Investment

Planning and shopping for a Round-the-World (RTW) ticket is a labor-intensive process. If you don’t enjoy planning a short trip, you’ll find it much more difficult to plan a complicated RTW itinerary. Personally, I enjoy the process, but then again, I also like airports and flying.

Also, before you can actually buy a Round-the-World ticket, you need to be willing to do all these things:

– Spend a couple of hours of initial reading

– Spend at least a couple of hours planning and optimizing

– Place an initial phone call (usually at least 30 minutes) setting up the trip

– Place a secondary phone call a few days later after the ticket has been validated

– Make any adjustments due to lack of availability or invalid routings

– Arrange to pay for the ticket with a local office in the originating country (this step may be optional, depending on how you structure the trip)

Those are the minimum “time costs” for getting a Round-the-World trip set up well. Keep in mind that you can use a RTW ticket for up to a full year, so taking the time to do it well is important. The value I receive from my tickets well exceeds the planning time it requires, but as noted, the practice is not for everyone.

Good Reasons to Use Round-the-World Tickets

If you’re willing and able to invest your time, the benefits you’ll receive from using these kinds of tickets are significant.

– Tremendous Value. RTW tickets are not especially cheap (see below for a cost outline), but a well-optimized ticket can provide value far beyond what it would cost to otherwise buy a series of one-way tickets.

– Freedom and Flexibility. I change my flights all the time, and with RTW tickets, it’s easy. Date and time changes are free, and you can make changes anytime — from far in advance all the way up to the day of departure. For a fee, you can even reroute the entire ticket after you’ve begun the trip.

– One Full Year. You get an entire year to use the ticket, which means that you can have up to 365 days of going from place to place, or you can get even more creative like I do and spread out the ticket into a series of shorter trips by finding a way to come home in the middle.

– Miles and Elite Status. I carry the highest-level elite status in two airlines thanks to my RTW travel. I also earned more than 200,000 Frequent Flyer miles with American Airlines in 2009, thanks to double-mileage bonuses and a lot of time in the air. With the status, I’m now first on the upgrade list, can hang out in nice airline lounges around the world, and don’t have to wait on hold when I call the airline.

– Creative Opportunities to Travel. You can get to a lot of places in the world with simple round-trip tickets, but because RTW tickets are priced by mileage or by segment, you can visit destinations that are otherwise cost-prohibitive when using regular tickets.

What to Do First

If you know this is what you want to do, or even if you’re just curious and want to create a sample itinerary, start by downloading these two free tools:

Star Alliance Mileage Calculator

OneWorld Timetable and Itinerary Planner

Spend some time getting to understand how they work. You’ll also want to check out the OneWorld interactive route map and the Star Alliance Downloadable Timetables to better understand where you can go.

WARNING: This software can be hazardous to your productivity. Many a workday has been lost at World Domination HQ because of the attraction of these tools. Don’t say I didn’t warn you.

Next, you need to answer a few questions: where do you want to go? What’s the goal of your trip? How much time do you have?

Star Alliance versus OneWorld

Each airline alliance has its own rules for how the ticket works. The one from Star Alliance is mileage based, meaning you’ll have a limit of 26,000, 29,000, 34,000 or 39,000 miles on your ticket. The trick here is to optimize your route to where you are just below one of the tiers, getting the best possible value without spending more money than necessary. (A friend of mine got his itinerary to 33,998 miles, which I thought was pretty good.)

The OneWorld product is segment-based, meaning that a flight from Hong Kong to New York (11 hours) is the same as a flight from Chicago to Dallas (less than 2 hours). You can have up to 16 segments on the trip, and naturally, you’ll want to optimize for flights that would be fairly expensive when purchasing a standard ticket.

I get even more creative with my plans, involving overland trips, return journeys to my home base in Portland, Oregon, and having multiple tickets open at one time. You don’t have to be that imaginative; I’ve been doing this for a while. Even a fairly basic RTW ticket can yield significant benefits and travel opportunities you wouldn’t otherwise have.

How Much Does it Cost?

The cost for either product mentioned above varies from $3,000 to $10,000 – largely dependent on travel class, mileage tier (Star Alliance only) and where you begin the trip from. My tickets over the past few years have been almost exactly $5,000 each. I purchased two of them last year, and I’m trying to set up a new one for early 2011.

$3,000+ is a lot of money, of course, but when you consider all the flights you can take, the price per segment goes way down. My price-per-segment is about $300 (now $400), and this includes many long-haul flights that would otherwise cost thousands of dollars.

For example, here is an itinerary I used for my first OneWorld RTW ticket:

NRT-HKG-LAX-SJO-LAX-ORD-SEA-JFK-SCL-IPC-SCL-EZE-ORD-AMM-TUN-AMM-FCO-HKG-NRT

This 18-segment itinerary, purchased before the limit dropped to 16, included:

– A trip to Easter Island, usually quite pricey since there’s only one easy way to get there (through South America on LAN Chile or LAN Peru)

– A visit to North Africa and the Middle East, another pricey region

– A quick trip down to Costa Rica, which provided more miles than most U.S. flights would have offered

– A return to Seattle (in between Asia and South America) where I could stop and break up the trip for a while

– Base mileage of 54,894 miles, which when added to a number of bonuses I received, came up to nearly 100,000 total award miles

– When combined with overland trips on location (to Uruguay from Argentina, to San Marino from Rome, etc.) the chance to visit 10 countries from this one ticket

Geographic Advantage

You can get the best deal on Round-the-World tickets by departing from (and eventually returning to) a few specific countries where the price is much lower than leaving from North America or Europe. Which countries? Well, they change from time to time, but as of the time I’m writing this (October 2010), the best places are South Korea, South Africa, Mauritius, Sri Lanka, and Indonesia.

Yes, it takes some work to get there. If those are too far, Japan is also a decent choice, where I began that first RTW trip. And of course, you don’t have to begin from a faraway place. If you don’t mind paying a fair amount more (usually $2000-4000), you can begin from North America or wherever you live. To get the estimate cost for your trip based on travel class, number of miles (Star Alliance only) and departing country, complete a mock itinerary on either of the two online fare calculators. You can then switch the departing country around to see how it compares with other options.

Reservations

Finally, when you actually get ready to buy your ticket, you’ll need to do two steps that may or may not be easy:

1. Create your itinerary. Until very recently, RTW itineraries usually had to be phoned in to an airline desk to set up manually. Thankfully, you can now set up a RTW itinerary online most of the time. In some cases there may be quirks in the itinerary that are allowed but not recognized by the online system, in which case you’ll need to phone it in. To at least get started online, use these links:

Star Alliance

OneWorld

If phoning it in, plan for the process to take at least half an hour once you get someone on the phone. It is much easier with OneWorld, since they have a dedicated RTW desk operated by American Airlines. With Star Alliance airlines, you may need to talk to several people before you find someone who knows how to create the itinerary in their system.

2. Find a way to pay for the ticket. I don’t mean, “Save the money,” although that of course is important too. I mean, “Find out how to physically pay for the ticket.” This is easy if you are buying online or are already in the country you are departing from. If you live in the U.S. and want to depart from the U.S., for example, then you can pay for the ticket after it is “rated” by the airline desk. In this case, you wait a few days after first phoning in the itinerary, and then call back to pay with your credit card.

If you’re beginning the trip in another country, it’s a bit more complicated. In some cases, you’ll need to phone the airline’s office in the country. I used Skype to do this last year with AA Japan. Some airline reps in overseas locations are more helpful than others, and of course there can be a language barrier as well. A certain amount of persistence may be required, but you can also get lucky and have it done in 20 minutes with the right rep on the right day.

7 Tips to Help Plan Your Trip

1. If using OneWorld, here is a very helpful validator that can help check your itinerary before going to book. It can also suggest alternative cities for more mileage.

2. Due to a quirk in airline rules, some countries in North Africa are defined as being in Europe for the purposes of ticket validation. You can visit Morocco, Tunisia, Algeria, or even Sudan as part of the “European” portion of your trip.

3. Similarly, “North America” includes the Caribbean and parts of Central America. You can visit Panama, Costa Rica, El Salvador, Belize, Honduras, Haiti, the Dominican Republic, and several other stops during the North America portion.

4. If you don’t know how you’ll use certain segments, you can book them as “open” (so that the ticket can be issued) and add the dates later. You won’t have to pay a change fee when you add the dates.

5. London’s Heathrow (LHR) airport has very high taxes. If you can avoid it, or use it for transit only (less than 24 hours), you’ll save quite a bit.

6. Most of the time, you won’t want to use Frequent Flyer miles for a Round-the-World trip. Instead, you can get better value by redeeming miles for two round-trip tickets between continents. You’ll then effectively have two RTWs for the price of one.

7. People often ask which airline program is best for them. It all depends on where you travel and what your goals are, but if forced to make a recommendation I usually send people to the AAdvantage program from American Airlines. Even if you don’t live in the U.S., AA’s program can help you. If you prefer Star Alliance, then most programs are equal.

8. Use at least part of your RTW ticket to visit destinations that are otherwise prohibitively expensive to purchase. Among others, I’ve gone to Kurdistan (Iraq), Pakistan, Burma, and Uganda as part of my RTW tickets. Each of these places is fairly expensive to travel to on a simpler ticket.

What to Watch Out for

I spent a couple hours writing out this information because I frequently get questions about booking RTW tickets, and while I try to respond to each request individually, I also like to send people to an online resource for more reading. When I went to look for more resources on Google, the majority of the first-page results for “Round-the-World plane ticket” and related terms contained inaccurate information from a biased source. How do you know the sources are biased? Because many of them lead visitors to book through an online travel agency where they receive commission.

When it comes to Round-the-World tickets, this is one time when it’s actually better to buy from the airlines instead of a travel agent or other reseller. Since these tickets aren’t usually commissionable (the travel agent doesn’t get paid much to issue them), some agents will play dumb or try to steer you towards an alternative kind of ticket.

If that’s what you want, of course, there’s nothing unethical about it. There are some situations when a DIY trip will be better, but in many other situations the alliance tickets are the best bet. I tend to think most people want the best kind of ticket for the lowest possible price, and once you understand how the process works, the OneWorld and Star Alliance products can be great options.

I hope to see you somewhere on a future Round-the-World stop. I’ll be in the lounge with my MacBook, probably responding to emails or planning a future trip.

###

If you’ve ever fantasized about taking time off to globe-trot, I would highly recommend Rolf Pott’s Vagabonding. It is one of only two books I took with me when I traveled the world for 18 months. Outside Magazine founding editor Tim Cahill calls Vagabonding “the most sensible book of travel related advice ever written.”

I recently partnered with Rolf to release the exclusive audiobook for Vagabonding. For more on this incredible book, click here.

Follow Chris’ live updates from every country in the world on Twitter. Be sure to also check out his new book, The Art of Non-Conformity, for which he’s currently visiting 50 states and 10 provinces. And I thought I traveled a lot!

Afterword: Some additional comments from Chris in the comments:

@Matt, yes, you have to go in one rough direction (East–>West or vice versa). However, the rule is based on regions, not strict geography – so you can bounce around in any given region before moving on.

@Muir, in addition to RTW tickets I also do a lot of Frequent Flyer (award) tickets. So in my case, often I’ll travel on a RTW ticket for a while, then go home to Seattle/Portland for a few weeks on a different ticket. I then return to the last point in the RTW trip and keep going. I’ve also done this with two separate RTW tickets, but that can get complicated.

@Enzo, being based in the UK (or anywhere else) shouldn’t affect much with RTW planning. The process is similar no matter where you are.

@Boris, you’re right – HKG-JFK should be 15 hours. My fault.

QOD: What is the greatest travel deal (airfare, housing, recreation, or otherwise) that you ever chanced into or made happen?

Related and Recommended

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 500 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.