Busy Saturday
March 29th, 2016
Civilian adventures on the first Saturday of Spring in New York. Filmed on March 26, 2016.
The stops: Sunset Park → B63 → Body Reserve → Berkli Parc → Lavender Lake → Pio Pio → N Train → Sunset Park
Equipment: Powershot S110
Music: YACHT – Paradise Engineering, Otis McDonald – Fingers

Congratulations to Yoko for a personal record on the squat (100lbs). You deserve a Cobb salad.
Morning Commute with No Face
February 28th, 2016
I watched “Spirited Away” when I was in the 8th grade. My best friend, Sean, and I got dropped off early at the theater and after raiding samples at the nearby Whole Foods we strapped in for a subtitled screening of Miyazaki’s anime adventure.

No Face on the train in Spirited Away…kind of like us…
Fast forward 15 years to this past Halloween where my girlfriend, Yoko, was dead set on spending the day dressed as No Face, unequivocally Spirited Away’s best character.
Here’s what I captured of Yoko in costume during our morning commute on the R train from Sunset Park to Soho.
How to Create an Exceptional Application Process
February 11th, 2016

Cat illustrations by Yoko Sakao Ohama
Since moving on, I’ve had the pleasure to meet remarkable people who also make an impact through events. From a women’s salon for changemakers that started in New York to a barber shop speaker series out of Detroit to a global community of educators, I find these projects not only inspiring but also fascinating.
Those interactions have motivated me to write a series of articles about scaling communities. This is the first, and it covers how to design a righteous application process. My purpose is to create the playbook I wish I had five years ago when I was figuring out how to expand CreativeMornings. If I can better equip one person who’s nurturing a network of people, mission accomplished.
If you happen to be a fine human who is convening a secret army of diverse, likeminded, passionate folks–don’t hesitate to email me. I’d love to learn more about what you’re up to and offer any help because I probably think what you’re doing is rad.
Thanks for listening,
Kevin
Great applicants deserve a great application
Whether you run a successful meetup and want to replicate it in other cities or you’re at the helm of a large online community that’s considering in-person events, you’re probably going to design an application process at some point. By collecting and reviewing applications, you’ll find local ambassadors (or whatever you decide to call them: organizers, partners, hub leaders, paladins) who can host your event in new locations.
An application is a great way to gauge interest, set expectations and save time (for all parties). Here are my three pointers for creating a great application process.
Tip #1: Respect people’s time
In marketing, the word “funnel” describes the stages a customer travels through to eventually buy your product. A bunch of folks go in one end, and they get whittled down to a few that actually buy.
If we look at our application process as a funnel, we start with some number of interested parties and after a series of checkpoints (e.g. an email, a written application, an interview) we choose a select group to join the inner circle. People “exit” along the way either by opting out or getting cut.
Conventional wisdom might say, “The more people entering the funnel the better.” So should we make the application easier to increase our leads? I prefer the opposite approach. Make it hard. Remind people they have alternatives. Create a high barrier to entry. If we’re not the right fit for one another, and I can suss that out sooner, let’s nip it in the bud (same goes for dating).
Think about all of the wasted hours and bad karma that result from rejected applications. Instead of the time sink that is sifting through a sea of no’s to uncover a few yes’s, I say treat your search for local ambassadors like the ideal apartment search: expend minimal effort to find exactly what (or whom) you’re looking for.
In short, respect everyone’s time; politely weed people out early.
Possible strategies:
- List reasons why someone shouldn’t apply – List them loud and proud. It’ll not only act as a filter but also set expectations.
- Make the application sneakily difficult – Nobody likes an unnecessarily long process, but consider incorporating a creative challenge like a video or sample blog post.
- Intimidate applicants with stellar examples – You want the person who says, “Wow, that’s impressive…but I can do better.”
- Make it social – Require team members or pre-approved references. Discussing the application with others is an uncomfortable step only the committed will complete.
Although aggressively weeding out prospects doesn’t make sense for every project, in the context of recruiting local ambassadors I’d argue it generates optimal results while minimizing squandered effort for everyone involved.
Tip #2: Get to know the humans
When my dad emigrated from Vietnam to the U.S. in 1975, he could only send letters back to his family for years. Today, he can pick up an iPad and watch chubby Vietnamese baby nephews eat their dinner in real time.
In-person meetings are best. The folks at Lean Startup Machine would literally travel to each workshop in a new city. If you can’t swing that, at least turn on the video and dig in. The fact that video chat exists is mind blowing. Use it and any other interactive tools to get to know an applicant beyond the qualifications.
This person is going to represent your brand to foreign audiences and whether you like it or not, he/she will be a direct reflection of your judgement. Get to know them on a deeper level.
Possible Strategies:
- Video chat – When you interview applicants, chat it up face to face. If they don’t speak English, suggest they bring along an interpreter.
- Incorporate video into the application – My favorite tactic we employed at CreativeMornings was asking for a 3 minute talk-to-the-webcam video.
- Ask weird questions – Interviews can get stale and predictable. Use unexpected questions to open people up. At CreativeMornings, our head of community Sally Rumble would ask,
“If you had unlimited money and a year of free time to make a documentary, what would it be about?”
- Make them attend – Require applicants to go to an event in another city and meet an ambassador
Tip #3: Make it official, sign something
I don’t usually celebrate new partnerships until ink is on paper. That’s partially my personality and partially because I’ve already made the mistake of pre-celebrating deals that have fallen through. Guh. You just never know what’ll happen until it’s all said and done.
In terms of bringing on a local ambassador, I advise folks building communities to draft at least a basic agreement. You can go full on like TEDx or just send a few bullet points via email and ask for a confirmation.
Either way, the exercise creates a moment where expectations on both sides are clarified. A simple way to start is to two lists: what you’ll do and what the new guy’s supposed to do. It might seem formal but one of the basic rules of business must be, “get it in writing.”
Possible strategies:
- Create an agreement – Cash in favors with that lawyer friend to draft a not-so-intimidating agreement between headquarters and ambassadors.
- Clarify expectations before the application – Another early filter! Have applicants accept terms long before submission.
- Walk through the agreement during the interview – Repetition, repetition, repetition. Give folks an opportunity to ask questions live.
I know you can’t think through every scenario (nor would I recommend it; that’s a recipe for high blood pressure). You’re going to make mistakes and you’re going to get burned (hopefully not too often). Take each lesson and ask yourself, how might I have avoided this situation by communicating an expectation earlier?
In the words of my friend Becky Wang,
“Every issue is a communication issue.”
In Conclusion
In summary, to build a great application process you should:
- Weed out applicants early by purposely making the process difficult. It’ll save everyone time.
- Meet in-person or use video to get to know applicants on a deeper level.
- Clarify expectations in writing. Getting on the same page will pay dividends.

I like to map out the application process alongside the complete user journey. With a flow chart like this, I get the big picture of an ambassador’s experience.
The best part of an application process is saying congratulations. If I had one more piece of advice on this topic, I’d recommend calling applicants to tell them the good news just like a job recruiter.
There’s nothing like seeing the excitement in an applicant’s face when they learn they’ve been accepted. Imagine the last time you got that sort of validation. The words, “application approved” feel really good.
You hold great power my friend. Put it to good use.
Special thanks to Yoko for reading rough drafts and drawing cats.
Broad Strokes vs. Fine Details
February 3rd, 2016
Taped to my fridge is a bucket list with item number one crossed off: “Learn to surf.”
I was parked on the sand six months ago, intently listening to a beach blond surf instructor named Andrew. With his perpetually wet hair, Andrew described the broad strokes of how to surf. I practiced paddling and standing up a dozen times on dry land before taking to the water.
As I gave each wave a go, Andrew came around and offered more pointed feedback. It felt like with every small surfing victory, he revealed another detail to focus on until eventually I popped up on the board and rode my first wave into the beach.
A New Mantra
Lately my motto has been,
“Broad strokes before fine details,”
which came to me long after the surf lesson while A/B testing websites.
A/B testing—also called split testing—is the process of testing two versions of a webpage to gauge which performs better. Say you run a stylin’ online shop that sells crafty enamel pins, and you’re curious if customers are more likely to buy when shown images of pins on clothing versus pins in their packaging.
Well, you can test that. After creating two variations of a product page with different imagery, you can use a tool to split website traffic to each version and measure which page leads to more $ales.
Now if you ran your A/B test for a day and the new variation sold five more pins, can you confidently call it the winner? Or was it a fluke? What you must also consider is the statistical significance of your experiment which depends on traffic, normal sales and what level of confidence you’re looking for. The bottom line is if you make a tiny change that causes a tiny effect, you might be waiting months for a result you can trust. That’s not very helpful, is it?
Hence, the strategy for low traffic websites is to avoid testing incremental changes like a red vs blue button. In order to detect a significant change, you must make a significant change–new imagery, a bold redesign or a very different marketing message. There was my aha moment: “Broad strokes before fine details.”
On Making
With websites we wireframe, with writing we outline and with film we storyboard. It’s through prototyping that we learn about the medium, sense what the final product might feel like and gain early indicators of how our audience will react. In other words, it helps to start by drawing with a thick sharpie. “Broad strokes before fine details.”
With each creative endeavor, I often feel like a dog chasing squirrels. I’m focused at the onset, but every few minutes my brain finds another unfinished detail begging for attention. “I should really change that text.” “That image looks like crap.” “This spreadsheet is so disorganized.” In my weaker moments, I chase the quick wins, making tiny, incremental fixes until I’ve forgotten what I was doing in the first place.
In “The Power of Habit,” Charles Duhigg compares willpower to a reservoir. You wake up replenished and throughout the day every decision slowly depletes your store of determination. I find similarities in tackling a new project. If you allow yourself to get distracted with every detail before you’ve even built the frame, you risk getting overwhelmed—and worse, giving up.
To fight back, just imagine a miniature version of yourself (or me) standing on your shoulder softly chanting, “Broad strokes before fine details.”
On Tinkering
There’s a caveat though: the fine details can be fun. On top of that, fun is important because achieving a goal requires “managing enthusiasm” along the way.1
How might we reconcile prioritizing broad strokes with the joy of fiddling with details? Thankfully, my father provided a sufficient answer. During a father-son chat about work-life balance my Dad once said,
“If you plan to have fun, commit to having fun.”
If you’re psyched about exploring a certain detail, explicitly make time for it. Tinkering can be powerful. (I’d even argue you should tinker with broad strokes before fine details, prioritizing the directions that differ greatly. You’ll learn more!)
Budget appropriately, experiment guilt-free and set an expectation for when you’ll zoom back out.
On Courage
From my perspective, what’s most difficult about teaching someone to surf is the part where you tell the new surfer, “Keep trying until you get the hang of it.” Listening to instructions and practicing on sand are only primers for diving in and giving it your best shot. There’s no substitute for trial and error.
I see creative pursuits the same way. Even a great idea marks only a starting point. You gather the courage to begin and through testing, prototyping (or just trying to stand up) you learn more about task at hand.
The mantra, ”Broad strokes before fine details,” helps you course correct along the way but the whole shebang starts with you making the uncomfortable decision to create something new.
In the words of Andrew the surf instructor, “When in doubt, paddle out.”

Andrew and me at Wavecrest Surf School in Jeffrey’s Bay, South Africa.
1. The phrase “managing enthusiasm” came from this book on A/B testing.
Thanks to Yoko for editing with broad strokes.
Adventures in the Wild #Snowmageddon2016
January 23rd, 2016
According to Slate, today was the snowiest day in New York City history. Yoko and I had prepared an impressive stock of provisions and were ready to weather the storm (i.e. not change clothes all weekend).
Nevertheless, 19 hours into our snack-heavy, Netflix-induced, Hearthstone-filled weekend coma, cabin fever got the best of us.
So we made this video.
#sunsetparksnowrampage
My Talk on Empathy and Growing a Global Community
November 8th, 2015
On September 25, 2015, I gave a talk on empathy at CreativeMornings. Note: my Justin Timberlake “My Love” entrance music with laser lights didn’t make the final cut.
The first speech I ever made was about the Great Purple Hairstreak butterfly. I was eight years old. This third grade class presentation would not only be my first foray into public speaking but also my first intensive public speaking training, courtesy of my mother.
Make eye contact. No note cards. Enunciate your words. Slow down. Smile. My poster was propped up on an easel, and I was given a long chopstick to use as a pointer. So ensued multiple rehearsals, each videotaped and carefully reviewed.
“Notice how you repeat the same hand gestures?”
“Count the ‘ums’ in your speech.”
Tears were shed, but Mom’s patience won the day as we ironed out the kinks, dropped the filler words and memorized my first five minute speech.

Obligatory photo of me mid-sentence making hand gestures. Photo by Tory Williams
This memory has been top of mind, as I had the honor of speaking in front of 300 people at the Brooklyn Academy of Music (BAM) for CreativeMornings/NewYork in September. After producing dozens of similar events, it was a nostalgic, humbling and slightly alien feeling to be invited to take the stage myself.
I spoke about scaling CreativeMornings from four to 100+ cities over four years—the strategy, highlights and challenges. It’s a personal talk about growth, community and empathy.
As I prepared, I had flashbacks to Mom’s public speaking bootcamp. Her lessons were timeless, and I know for a fact she has proudly watched my recent talk at least twice. Thanks to the CreativeMornings crew for the wonderful opportunity to cap off my time on the team, and thank you for listening.
Watch the talk here, and there’s also a Q&A. →
Footnotes from the talk
- The montage sequence from 500 Days of Summer I rewatched obsessively. The song is “Vagabond” by Wolfmother. (00:50)
- This is Jerri Chou, Co-founder of The Feast. (01:55)
- This is Tina Roth Eisenberg, Founder of CreativeMornings. (02:50)
- This is Craig Shapiro, Founder of Collaborative Fund. (05:46)
- Douglas Atkin’s quote on why people join cults comes from his book, “The Culting of Brands.” (08:10)
- The animated gif is of “No Face” from the Miyazaki film, “Spirited Away,” which also happened to be my girlfriend’s Halloween costume this year. On the same topic, I highly recommend Paul Graham’s essay on resourcefulness. (11:37)
- One of my favorite business books, “Give and Take” by Adam Grant (12:32)
- Current full list of CreativeMornings cities. Find an event near you! (13:17)
- fingerspitzengefühl (13:42)
- A blog post reflecting on my experience at the 2012 CreativeMornings Summit. (17:51)
- Stiles Hall is the nonprofit led by David Stark which organizes the “Facing You, Facing Me” course at UC Berkeley. If you’re interested in learning more about David’s class that’s been going on for over 30 years, I recommend this video from the documentary “What’s Race Got To Do With It?” (21:15)
- How I packed and booked my RTW ticket for my world trip. Also, here’s the video recapping that crazy three month adventure: Around the World in Kevinty Days. (24:45)
- My new company, Classcraft, is helping teachers engage students by transforming the classroom into an immersive role-playing game. (26:31)
From the Q&A
- My favorite CreativeMornings talk, Benjamin Salka from the Story Pirates. (01:16)
- I’m referencing the Hedgehog Concept, which was made famous by Jim Collin’s in his book “Good to Great.” (03:40)
Beginners Guide to Booking a Round The World Plane Ticket
August 13th, 2015

Along the walk from Bondi to Coogee Beach in Sydney, Australia during my RTW trip.
Small warning: If you’re not the type of person that thrives on hacking your way to efficiency and maximizing the effectiveness of your dollar, a RTW ticket may not be the right choice. It’ll undoubtedly require patience and a few dozen hours of planning. Also, I’m no expert. Just a guy that did it. Personally, my first step was to consult the blog of Chris Guillibeau, a man I briefly met who traveled to every country and wrote a fantastic starter guide.
This post attempts to explain the basics of a RTW trip and what it takes to actually book the ticket while linking to a number of resources I found helpful. For my recent trip, I used the oneworld Explorer ticket, so the more specific points in this guide are gleaned from that experience. If you’re a RTW sensei and spot anything inaccurate, let me know in the comments.
Planning an adventure to unknown places can be equal parts stressful and exciting, but always well worth the effort. Best of luck and enjoy the ride.

Moai statues buried at the quarry on Easter Island
Table of Contents:
1. What is a Round The World (RTW) ticket?
1.1 My Trip
2. Benefits
2.1 Price
2.2 Flexibility (sorta)
2.3 Constraints
3. Planning your trip and how it works in practice
3.1 Different types of tickets
3.2 Understanding the rules of the oneworld Explorer
3.3 Using the oneworld planning tool
3.4 Surface segments and separate flights
3.5 Where to start your trip
3.6 Language and abbreviations
4. Booking your trip
4.1 Booking with American Airlines
4.2 How booking works
6. FAQs
1. What is a Round The World (RTW) plane ticket?
Wikipedia will tell you that a Round The World ticket, abbreviated as RTW, is “a product that enables travellers to fly around the world for a relatively low price.” I like to think of a RTW ticket as:
a special, flexible plane ticket that enables you to fly literally around the world on a single itinerary
The most common RTW tickets are issued by airline alliances (e.g. oneworld, Star Alliance and SkyTeam) and allow you to travel using any of their partner airlines. For instance if you booked a oneworld Explorer RTW ticket with American Airlines like I did, you would have access to British Airways, LAN Airlines, Japan Airlines, Qantas Airways and more.
Usually, RTW tickets also:
- require you to start and end in the same place
- last one year
- require travel roughly in one direction
- allow you to change dates without penalty
- charge fees for re-routing your itinerary
- come with unique rules (e.g. 16 total flights or 34,000 miles of travel)
I booked the following RTW ticket through AA on the oneworld Alliance:
Johannesburg, South Africa -> London, England -> (surface segment) Paris, France -> New York, USA -> Buenos Aires, Argentina -> Lima, Peru -> Easter Island, Chile -> Santiago, Chile -> Tokyo, Japan -> Sydney, Australia -> Johannesburg, South Africa.
Note: this was not my entire itinerary. You can see that in the map below.
A confusing map of my full itinerary (including RTW flights and other modes of transportation)
I supplemented my RTW ticket with a variety of trains, buses and other budget flights. More on that here.
2. Benefits
So why use an RTW ticket versus simply booking separate flights? I boil it down to three main reasons.
2.1 Price
If employed appropriately, a RTW ticket can save you significant money on an ambitious itinerary. Though I flew Economy, I’ve heard the best value occurs while flying Business or First. A Business RTW ticket may be twice as expensive as the same trip schlepping in Economy, but a Business seat can be 3x the price of Economy on a normal flight. The total price of your ticket will be mostly based on itinerary, cabin class, and city of origin.
On his blog, Nomadic Matt states that:
“RTW tickets prices range between $2,700–$10,000 USD, depending on your mileage, route, and number of stops. A simple two- or three-stop RTW ticket might cost as little as $1,500 USD.”
During my own planning with the oneworld Explorer, I made different itineraries with 4-6 continents and was quoted prices all over that range.
2.2 Flexibility (sorta)
RTW tickets allow you to easily change the dates of your flights (as long as there are seats available). For instance, I locked in my initial reservation, then decided I wanted one more day in Peru and Australia. I called the American Airlines RTW Desk (1-800-247-3247). After a few minutes on hold I explained my changes, and they were instantly booked.
However, RTW tickets do require you to plan your trip out in advance. It can be more of a draft, but you’ll still need to select destinations and flights. If you’re seeking a more open-ended, impromptu, soul-wandering journey that doesn’t have a predetermined (at least on the macro level) itinerary, RTWs might not be the best fit.

The view from the Arc De Triomphe in Paris.
2.3 Constraints
I believe that creativity flourishes with constraints. Tell me to make something, anything, I’ll have a hard time getting started. Hand me two clothes hangers and with a bag of marshmallows and say make something, I’ve got five ideas. Planning a world trip is daunting. Where do I want to go? How long do I want to stay? How do I get the best value? It’s an amazing opportunity, but it can also leave your brain in a knot.
I found the rules of the RTW ticket a bit liberating. Knowing I could only fly so many times in one continent helped pair down the possibilities. Because I had to fly in one direction (roughly), I had a better idea of the order of destinations. Sometimes, guidelines can be your best friend.
3. Planning your trip and how it works in practice
So you’re into the idea of a RTW ticket! Cool beans. Here was my basic trip planning process. We’ll cover booking next.
- Choose an alliance and ticket type (I picked the oneworld Explorer)
- Make a dream list of destinations
- Use the online RTW planning tool (and other helpful links) to try out different itineraries
- Freak out, totally change your plans.
- Decide on your final itinerary, including specific flights and the total cost
3.1 Different types of tickets
From what I’ve read, there are two main types of tickets to consider: mileage-based or segment-based.
Mileage-based
You can book a mileage-based RTW ticket with any of the major alliances and you’ll be allotted with a certain amount of miles to travel. For instance, with oneworld you can choose the Global Explorer which will calculate the cost of your ticket based on tiers of miles traveled: 26,000, 29,000, 34,000 or 39,000 miles. For a sense of scale New York -> London is about 3,500 miles. Use this tool for more fun flight math.
Segment-based
oneworld offers a second product, the oneworld Explorer where the cost of your ticket isn’t based on total mileage but rather on the number of continents you visit (and the cabin class you choose).
In the end, I went with the oneworld Explorer segment-based ticket because:
- The goal for my trip was to see many, new faraway places over three months. The non-mileage-based ticket would help me do that.
- Based on my cursory internet research, it seemed that oneworld’s online tool was functional and customer support specifically through the American Airlines RTW desk was legit.
- I wanted to accrue miles on American Airlines as an existing AAdvantage frequent flyer.
3.2 Understanding the rules of the oneworld Explorer
RTW Tickets come with many rules and guidelines that you need to understand well. I’ll outline a few important ones for the oneworld Explorer. Truthfully, I found oneworld’s documentation lacking. The most helpful information came from third party resources like this in depth thread on flyertalk. Nevertheless, read the official rulebook closely–it’ll help you comprehend how to create a valid itinerary.
Let’s review a few important oneworld Explorer guidelines:
- One Year
“Return travel from the last stopover point must commence no later than 12 months after departure.” - 16 Flights Max
“A minimum of 3 and maximum of 16 segments, including surface segments between any 2 airports, are permitted for the entire journey.” - One direction around the globe
“Travel must be in a continuous forward direction.” Exact geography is not used, just East or West with respect to the continents. (e.g. you can’t go N. America -> Africa -> S.America.) - Can’t backtrack to your origin city
“Travel may not be via the point of origin.” - Otherwise, backtracking within a continent is cool (mostly)
“Backtracking within a continent is permitted except as follows: Backtracking between Hawaii and other points in North America is not permitted.” - Once you leave a continent, you can’t come back (mostly)
“Only one intercontinental departure and one intercontinental arrival permitted in each continent except as follows…” However, they make a few exceptions such as allowing an additional transfer through N. America. I presume this is because there are a few intercontinental legs that are hard to accomplish without a transfer elsewhere.
3.3 Using the oneworld planning tool
oneworld offers a pretty user-friendly web app for planning your RTW trip. Essentially, you populate a map with your desired cities in a particular order. The system notifies you if your itinerary violates any of the RTW rules and will not let you continue to the flight selection phase until you’ve inputed a complete, valid itinerary. You can save multiple itineraries and access them later.
Once your city order is set, you select each individual flight and its respective date from all of oneworld’s partner airlines. Finally, with all flights identified the computer spits out a price based on the cabin class you’ve selected (i.e. Economy or Business).
Remember, the flights you choose can be more of a first draft since you can make date changes with no fees. However, any routing changes, including one of the cities you’re connecting through, will result in additional fees ($125 not including changes in overall fare cost).
3.4 Surface segments and separate flights
As I mentioned earlier, making the most out of your RTW ticket means utilizing your flight segments effectively. The following was the RTW itinerary I booked with American Airlines:
Johannesburg, South Africa -> London, England -> (surface segment) Paris, France -> New York, USA -> Buenos Aires, Argentina -> Lima, Peru -> Easter Island, Chile -> Santiago, Chile -> Tokyo, Japan -> Sydney Australia -> Johannesburg, South Africa
However, my actual itinerary looked more like this:
New York, USA -> Cape Town, South Africa -> Port Elizabeth, South Africa -> Johannesburg, South Africa -> London, England -> Berlin, Germany -> Prague, Czech Republic -> Amsterdam, the Netherlands -> Paris, France -> New York, USA -> Buenos Aires, Argentina -> Lima, Peru -> Cuzco, Peru -> Lima, Peru -> Easter Island, Chile -> Santiago, Chile -> Tokyo, Japan -> lots of cities, Japan -> Osaka, Japan -> Tokyo, Japan -> Sydney Australia -> Johannesburg, South Africa -> New York, USA
Surface Segments
You’ll see that London -> Paris on the RTW itinerary was a “surface segment,” which is a fancy way of saying “I don’t need a flight. I’ll figure out how to get there myself.” I arrived in London and departed from Paris, making my way “over the surface” however I wanted.
I wanted to travel through Europe by train as well as enjoy a bit more flexibility during my three weeks there. Plus, flying between multiple European cities didn’t seem like an effective use of my precious flight segments. Note: that surface segment still counted toward my total number of segments, though it was not a flight.

Me with an unidentified expression at Machu Picchu during the Winter Solstice.
Separate Flights
Another example: I visited Machu Picchu in Peru during my trip. To get to get there, you generally depart for a trek from Cusco which is a short flight away from the larger airport in Lima. Instead of using my RTW itinerary to book a roundtrip from LIM -> CUZ (which would cost me two valuable flight segments in South America), I booked those flights separately with British Airways Avios points. I used those saved segments to get to and from Easter Island (about a six hour flight from Santiago) which is a much more costly roundtrip.
Your origin city plays a large factor in the total cost of a RTW ticket because of associated taxes. If you play around with your itinerary, you’ll see that starting in certain areas like the U.S. and the U.K. dramatically ups the quoted cost. Here’s a trip advisor thread where people discuss cheap places of origin. Some of the mentioned countries include South Africa, Japan and Jordan.
Keep an open mind about where to start your trip and consider other options like a separate roundtrip flight to get to your starting place. This could reduce the total cost of your adventure.
3.6 Language and Abbreviations
You’re bound to have questions during this planning process, and when you start googling you’ll realize that there’s a whole language associated with RTW tickets. Here’s a quick rundown, mostly gleaned from this thread on flyertalk, that’ll help you decipher all of the information out there.
Frequent flyers usually refer to a particular RTW itinerary with a short abbreviation that denotes basic information about a trip. For example, my itinerary is called a LONE6.
- L refers to the cabin class, A for First, D for Business, or L for Economy.
- ONE refers to the oneworld Explorer ticket.
- 6 refers to the number of continents which could be 3-6.
Hence, a DONE4 would be a Business class oneworld Explorer ticket through four continents. Check flyertalk for a more complete glossary and many helpful posts.
4. Booking your trip
So you’ve setup your trip on the oneworld website and it’s quoted a price for you. Depending on your itinerary, you may be able to follow the instructions and simply pay online. However, as The Points Guy mentions in this post:
“Here’s where things got a little sticky. You see, that handy Oneworld RTW planning tool should theoretically accept payment for your RTW. But as it turns out, the payment part often doesn’t work, so many will need to do it the old-fashioned way and call one of the member airlines’ RTW desks.”
4.1 Booking with American Airlines
Regardless, I recommend you book your RTW ticket by phone. Your ticket needs to be issued by a single airline and it seems that American Airlines is highly recommended as the carrier of choice. In theory, any of the oneworld airlines can register this itinerary for you, however AA has a dedicated hotline (the RTW desk available at 1-800-247-3247) and generally seems to have their act together.
The airline you book with will be the airline you’ll need to call to make any future itinerary changes and the last thing you want is to be passed from customer service rep to customer service rep in search of a soul who knows what the hell a RTW ticket is. The oneworld website will default to booking your trip with the carrier of your first flight segment but you can call AA on your own and book the RTW ticket as long as you have one of your trans-ocean segments planned with them. In other words, you can’t book an RTW ticket with AA if you don’t have a long flight with them on your itinerary.
Here’s how it works in practice from my experience:
- You will call the RTW desk and read them out loud your full proposed itinerary including cities, airports, flights and dates.
- They’ll take everything down (quite efficiently) and check to see if the computers deem your trip valid.
- If it checks out, they’ll provide you with a record locator (a short code) that holds all of the information about your potential trip. You can then proceed with payment.
Important: If you’re trying to book a RTW trip with the city of origin outside of the U.S., you may need to follow up separately with a local representative. You would provide him/her with your record locator, and pay in the local currency. Here’s an example of folks discussing the process for booking a trip starting in South Africa.
After all is said and done you’ll receive a confirmation and will be able to login to the American Airlines website to see one (very) long itinerary under a single reservation. Boom.

Sun rise during a game drive near Kruger in South Africa. Unbelievable.
5. Other Pro-tips
- If you’re traveling via train check out seat61.com
This guy goes into such deep detail about trains all around the world and the best ways to book. Super helpful. - British Airways Avios points can be very useful
BA points are great for some short international flights. Plus, Chase Sapphire Preferred points can be easily converted to Avios. I booked a business class flight from London to Berlin for 9,000 points + booking fees (and I also ate so much food in the BA lounge at Heathrow). You can even book that Lima -> Cuzco roundtrip using Avios with BA’s One World partner, LAN Airlines, but you’ll need to book it over the phone as the flights aren’t shown online. (Make sure to ask for them to waive the phone booking fee.) - You don’t need to book your Machu Picchu trek in advance (unless you really want to hike the Inca Trail)
If you’re planning a Machu Picchu trip, you’ll have to decide whether or not you want to hike on a multi-day trek or take the train. I wanted to trek but had read that permits to hike along the Inca Trail book up months in advance. Thinking I was late to the party, I figured the train was my only way to get up there. Upon arriving, I learned that there are plenty of other treks available to Machu Picchu, and while they don’t follow the ancient trail many are still awesome and sometimes even preferred. You can also book on very short notice. - Watch out for British Airways segments during your RTW
BA charges high fuel surcharges that can add up. It’s just worth checking to see if using another airline makes a large difference in cost. - Get a card with a chip and no foreign transaction fees
Like many, I primarily use my Chase Sapphire Preferred card. There’s no foreign transaction fee so I can pay in any currency without fear of additional charges. Also, many countries only accept credit cards with chips (rather than the magnetic strip).
6. FAQs
Q: You mentioned that the most common RTW tickets are issued by alliances. What are the other options?
A: Apparently there are specialized agencies, I don’t know much about them. This Wiki Travel entry mentions some.
Q: Of the places you visited, what was your favorite?
A: The most amazing sight to see: Machu Picchu. The most l I-can’t-believe-I’m-here: Easter Island. The most fun-to-travel-through-overall: Japan. The most-memorable-tourist-experience: safari in South Africa. The most I-wish-I-lived-here: Sydney.
Q: How did you keep track of your full itinerary (RTW + all of the little side trips)?
A: With a set of Google spreadsheets like this. I also added all flights and where I was staying each night to Google Calendar which was shared with my family.
Q: What did you pack?
A: Check out this blog post. I used a 35L backpack that was always carry-on.
Q: What sort of accommodation did you use throughout your trip?
A: Mostly I stayed with folks I’d met while working for CreativeMornings. Otherwise, a sprinkling of everything else you can imagine: hotels, hostels, Airbnb, overnight trains/flights. Unexpectedly, I became a fan of booking.com.
Q: What’s the best thing you ate?
A: Three-way tie between Okonomiyaki in Hiroshima, lomo a lo pobre in Santiago and fondue in Paris
Q: What’s the worst thing you ate?
A: This crap pasta from a pizza shop in Amsterdam. It was late. I was desperate.
Q: Best night?
A: A long walk in Tokyo that led to a neon-color-changing ferris wheel at night that led to winning the jackpot at an arcade medal game.
Q: How does making changes to your RTW itinerary work after everything is booked?
A: I only did this a handful of times but it was extremely easy with American Airlines. I called the AA RTW Desk, provided my identification info, and requested a few date changes. They immediately responded with my flight options and booked it all within a few minutes. Very impressive.
Q: Can I earn miles while on a RTW ticket?
A: You betcha. Standard advice would be to attempt to accrue as much mileage as you can with the same airline. While booking with AA, I provided my Frequent Flyer # and they credited as many flights as possible to my AA account. I did my best to choose AA flights while planning and actually all of the flights with partner airlines also counted.
Q: Do I check-in with the airline I’m flying with or the airline that I booked the RTW itinerary with?
A: The airline you’re flying with. However, online check-in is sometimes a bit of a toss up. My AA record locator worked on most partner airline websites. A few times, like with Japan Airlines, I had to first go to aa.com and was then redirected to JAL when I followed the check-in instructions.
Q: After going through the booking process, anything you would do differently while planning a RTW trip?
A: I’d probably try to remain a bit more flexible with my timing. Easily switching dates is one of the major advantages for a RTW ticket, one which I did not employ often. However, there were a few moments–like realizing a big festival was coming to town or that a friend would be in the same place by coincidence–where I wish I had been open to change.
Q: Are there alternative uses for RTW tickets?
A: I stumbled across a few examples of people employing some advanced travel planning techniques. For example, someone might use a RTW ticket for a few trips spread out over a year and buy separate flights to “continue” the itinerary. Or Chris mentions using multiple simultaneous RTW tickets, which just sounds way over my head.
Q: I want to go to Easter Island. How long should I stay?
A: I stayed for four nights, and I thought it was perfect. There’s a good amount to do on the small online. I spent one day on a guided tour, another renting a jeep with new friends to see our favorite sights, and another day hiking along the cost solo. There are volcanos to hike, an underwater Moai you can scuba dive to, and beaches to hang out at. This thread was helpful. Beware: island weather can change very quickly. Before I arrived, flights were delayed for five days.
Q: How much time did you spend on airplanes over those three months?
A: 140 hours