Booking Around the World Flights

From Luxx to Minimal Bucks: learn our hard-earned tricks from over 5 years traveling the globe

By Ben Gelsey

Is your travel bucket list perennially growing? For me, it is. Travel destinations are like knowledge --- the more you know (or go), the more you want to know (and go). While I may have visited 21 countries ... There's still 174 more of them after all!

The ever-growing collection of Google Docs about all the places in the world I want to visit...

For people like us, an around the world trip (RTW or "round the world" trip in travel pro lingo) might be just what the doctor ordered. The idea is to spend 3-12 months on a focused, global itinerary of 5-10+ destinations to get your travel fill. While not everyone's schedule allows for this kind of travel, in my experience it is incredibly rewarding (& efficient from a cost-of-flights standpoint).

Though I don't call my trips "RTW" (since it's just my regular life, working online on Flights Machine & traveling), I typically spend 6-9 months away from the USA at time, batching together various destinations much like a traditional RTW trip would. In the past, I've done:

  • 7 months going through Bangkok, multiple cities in India, Kuala Lumpur and Barcelona
  • 7.5 months in China, Bali & Taiwan
  • 10 months traveling Europe (Zagreb, Amsterdam, Barcelona) and Asia (India, Malaysia, Thailand)
  • 7 months visiting the beaches/islands of southern Thailand, India, Seoul, Osaka + Kyoto + Tokyo and Indonesia

Some of my photos from Anjuna beach in Goa, Shenzhen, Bangkok, India and Barcelona

Despite this (and my other shorter trips not mentioned, such as to Central & South America), my travel bucketlist is longer than ever and so I've been thinking about doing a classic around the world trip. In this post, I want to share with you what I've learned about the best options for doing one of these trips.

In this post we'll cover:

  • Booking as 1 ticket with an airline alliance (and why that's a bad deal)
  • The ultimate luxury experience: ANA RTW in Business Class
  • Using Google Flights "Explore Destinations", eightydays, Kiwi and AirWander to find the cheapest Flights
  • Introducing the 3/4 RTW Trip (my crazy idea of skipping the Pacific)

Booking as 1 ticket with an airline alliance (and why that's a bad deal)

There are 3 major "airline" alliances, One World (includes American Airlines), Star Alliance (includes United Airlines) and SkyTeam (includes Delta). For around the world tickets, you're going to need to fly on many different airlines and if you wanted to buy it as 1 ticket all the airlines would need to be part of the same alliance (whereas if you buy multiple tickets you can mix and match any airlines).

Therefore, all 3 major alliances have special websites where you can purchase these tickets:

Now, it would be one thing if the airlines gave you a discount for "buying in bulk", so to speak, but they don't. As you'll see below, a simple 6-flight around the world itinerary on One World (New York - London - Athens - Amman - Bangkok - Tokyo - Los Angeles) costs a whopping $4,459.

This pricing is absurdly high for what you get...

Sadly, all 3 alliance websites are similarly high priced with a cumbersome UI for picking flights as well. These sites are basically a relic from the pre-internet era when you'd substantially benefit from having all your flights on one ticket for organization & logistical purposes. These days, it's no longer worthwhile versus just booking the flights individually.

Now, before we get into the tips for how to book your flights individually, I wanted to share an aspirational RTW trip where you get to fly around the world in BUSINESS class all for under $1000 (usually).

The ultimate luxury experience: ANA RTW in Business Class

As mentioned in my previous post I'm somewhat of a miles collector. A few of the different airline mileage programs offer special around the world awards, for example:

  • Qantas (140,000 miles for economy, 280,000 for business)
  • Korean Air (140,000 miles for economy, 220,000 for business)
  • Lufthansa (180,000 miles for economy, 325,000 for business)
  • Air Canada (200,000 miles for economy, 300,000 for business)
  • Singapore Air (180,000 miles for economy, 240,000 for business)
  • ANA (85,000 miles for economy, 125,000 for business)

Notice any outliers in the above? Amazingly, ANA offers a RTW award ticket in business class for less than most of the other airlines offer in economy!

For 125,000 miles you can fly up to 22,000 physical miles stopping in as many as 8 cities around the world! This is absolutely insane value. The taxes & fees on the award ticket can range from around $300 - $1500 depending on what specific airlines you fly (some airlines charge high "fuel surcharges" as part of their taxes & fees, even on award tickets).

Here are some real-life itineraries people have went on, mostly pulled from reddit:

Example 1

Example 2

Example 3

For more examples, click here.

The challenge here, is finding award flight availability for as many as 8 flights all on sequential dates that work with your schedule... Even for me, as an experienced award traveler, this isn't easy. The most efficient way to search is by using ExpertFlyer, rather than the airline websites.

If there's interest, in a future post we'll dive deeper into all the nitty gritty rules & requirements of the ANA RTW program and the exact methods for earning the necessary points and getting yours booked. Send me an email at [email protected] if this is a topic you want to know more about.

Using Google Flights "Explore Destinations", eightydays, Kiwi and AirWander to find the cheapest Flights

When planning an around the world trip DIY-style, first focus on the longest, most expensive flights and then fill in the gaps. For example, start with the transatlantic flight (TATL in travel-pro lingo).

While you may really want to visit Berlin, don't limit your search to $YOUR_HOME_CITY --> Berlin. Intra-europe flights are incredibly cheap these days, so focus on finding the cheapest flight to any city in Europe. While Google Flights doesn't make it obvious, the magic tool is when you click "Explore Destinations" in the bottom right corner of the screen.

Visit the Google Flights home page to see this link, after you do a search it cannot be found

In the "Explore Destinations" page key an eye out for nearby cities that are cheaper to fly your TATL to than your target city. Almost certainly, the city you want won't be the cheapest.

Berlin is $238 one-way ... But Rome and London are as low as $160!

Now, most likely you will want to visit a handful of cities in Europe. Planning the optimal routing used to be fairly time consuming until an outstanding tool called eightydays was released.

Now this is a bucketlist-checking trip! Rome, Vienna, Mallorca, Barcelona, London, Milan, Venice and Florence all for $234

But! Before you go any further, again, think about where you are going after Europe. Africa? Middle East? Central Asia? India? Or skipping all the way to South East Asia / East Asia?

Depending on what you choose, will dictate your search parameters for eightydays. Specifically, using Google Flights Explore Destinations you should find the cheapest flight to your next destination (from any city in Europe) and then use that as your final destination in eightydays.

Here's where it gets tricky --- Google Flights Explore Destinations only allows you to input 1 origin, where in this case we want to consider all of Europe as our origin...

To effectively search, you have a few options:

1.) The simplest way is to simply "brute force" Google Explore Destinations and simply click a bunch of likely cheap origins one-by-one... This is the most accurate, but the slowest.

2.) As an alternative, temporarily use the "roundtrip search" with your actual destination inputted as the origin. This will give you a rough sense of which actual origins are cheaper, and then you can perform the one-way search for each of those origins.

If I wanted to go to Mumbai next, set that as my origin and see which round-trips in Europe are cheapest

3.) Use, which allows you to input arbitrary geographical regions as both your origin and destination

Though most results will be for the same city on different dates, if you scroll enough you will get a sense of things

The other nice thing about Kiwi is that it often stitches together separate tickets. For a layover, this can be awkward (e.g. if the first flight is delayed). But for the world traveler, this indicates that you can get a free stopover. Meaning, you can stop in the intermediate city for as long as you like, effectively getting to visit an extra city for free.

Here we see that if flying from Stockholm to Mumbai, since it is 2 separate tickets we can stop in Dubai "for free" and visit that city as well.

Unless you've already been to the stopover city and disliked it, I highly recommend leveraging these free stopovers. It's a great way to broaden your "travel taste" and discover awesome places you never would have considered.

The ultimate site for discovering free stopovers is AirWander. AirWander is an incredibly innovative flight search tool that specifically focuses on discovering these free stopovers.

Just like Kiwi, AirWander pegs Dubai as the best way to get between Stockholm and Mumbai

In AirWander, we can see that if we tried to fly directly from Stockholm to Mumbai on one ticket it would actually be $27 more expensive than stopping in Dubai. The Kiwi way is stitching together these two tickets with a layover (and their "Kiwi Guarantee" to protect you in the event of delays), but the AirWander way is to stay in the city for at least a few days in a proper stopover.

Now, if the above is too much work, Kiwi does offer a shortcut tool called they call "Nomad" search. You just plug in the destinations you want and they try a bunch of different orderings until they find the cheapest path. This tends to work OK, but the more manual solution will usually find better results.

A sample NYC - Paris - Mumbai - Bangkok - New York itinerary for $1,031

Now... In the above screen you might have noticed something strange on the final flight. Kiwi has determined that the cheapest way to return from Bangkok to New York is to fly EAST. Due to Norwegian Air causing TATL prices to plummet, these days it is often cheaper to fly BACK across the atlantic rather than crossing the pacific (which has no budget airlines pressuring prices downward).

Returning the long way...

This leads to the new RTW trip that I've coined the "3/4 RTW", since after all you are only going are 3/4 of the world.

Introducing the 3/4 RTW Trip (my crazy idea of skipping the Pacific)

One day I was playing around with Google Flights Explore Destinations and came up with the following route:

  • LAX --> LGW ($160)
  • LGW --> ARN ($59)
  • ARN --> DXB ($94)
  • DXB --> BOM ($77)
  • BOM --> DMK ($102)
  • DMK --> NRT ($85)
  • NRT --> DPS ($147)
  • DPS --> SIN ($43)
  • SIN --> ATH ($173)
  • ATH --> BCN ($61)
  • BCN --> JFK ($156)

That's Los Angeles - London - Stockholm - Dubai - Mumbai - Bangkok - Tokyo - Bali - Singapore - Athens - Barcelona - New York for a total of $1157.

12 cities spanning the globe for under $1200.

Now... Although the above flights were all found on Google flights explore, the exact dates are out of order. So this represents a theoretical best and in actuality getting the dates to line up might add a few hundred dollars more. But, I am strongly convinced the 3/4 RTW has incredible promise.

In the coming weeks we are going to be posting more about the 3/4 RTW and if there's interest even sending out a real, bookable 3/4 RTW itinerary.

If visiting 10+ cities for under $2000 in airfare has got you hyped, email me at [email protected] and I'll share with you my latest info.

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