As I’m heading out, people have had lots of questions for me about booking Round the World flights. Namely, how do you do it? And just how expensive is it?

It’s taken a long time to get the flight thing figured out – especially with wanting some level of flexibility to take care of anything that might get delayed, cancelled, etc. I’d hate to have everything booked back to back, get delayed in the Philippines, and then have the whole trip thrown off.

Given that, I had a few options:

1. Buy a Round the World ticket from one of the major carriers
Before I actually quit my job to make this a reality, I always thought this was the way to go. OneWorld, SkyTeam and Star Alliance all have great trip planners and flexible tickets. When I was dreaming about taking a trip like this, I spent a decent amount of free time playing with those planners and pricing trips out.

Ultimately, while these have some options for flexibility and allow you to rack up a ton of miles on one group, these were too expensive and too restrictive for my tastes. When you’re flying on one airline group, some of the connections I’d have to make would be out of the way and inconvenient.

My estimated cost going this route: $5,500 – $7,000

2. Buy a Round the World ticket from a broker like AirTreks
AirTreks has an awesome planner for all sorts of routes and flights. I only discovered this option after I resigned to make this trip a reality.

AirTreks gives the advantage of a RTW ticket without the disadvantages of only having one airline group to fly with. They also get to take advantage of cheaper flights and flight options, so their total cost is much more reasonable than one of the big groups.

For a while, I thought this would be the way to go. And ultimately, maybe I should have gone this route. But again, I wanted a bit more flexibility than they offer. Also, adding a ton of regional flights would have made this really add up – and booking those on my own isn’t so difficult.

My estimated cost going this route: $3,000 – $4,000

3. Buy a series of one-way flights to get myself around the world
This is definitely the most DIY option. It’s also taught me all kinds of things about the most economical ways to book flights.

Sites like Kiwi are great for figuring out the most economical destinations to fly to after each place, and were incredibly helpful for me figuring out the route.

And then there’s Skyscanner – my new favorite site. Skyscanner has excellent price alerts, and seems to have found a few incredible deals that I couldn’t find anywhere else. For example, my flight from Tampa to Cebu, Philippines – Skyscanner found it for $720. When I looked at it on Air Canada’s site (that’s the airline Skyscanner found), it was coming in at about $1200.

Skyscanner also seems to do a far better job than any of the American aggregators on scanning low-cost Asian airlines like Cebu Pacific and Air Asia. It’s an incredible tool for playing with, but definitely takes some time to figure out the best plan.

One area Skyscanner is coming through for me is looking at flights from Yangon, Myanmar to Kathmandu, Nepal. When I search there for Yangon to Kathmandu, the flights are about $320 on my dates. I noticed they all also had layovers in Kuala Lumpur.

So then I searched Yangon to Kuala Lumpur; and then Kuala Lumpur to Kathmandu. Jackpot. Yangon to KL is about $50 on AirAsia, and KL to Kathmandu is then about $90. So I’ll save a ton of money by adding some time in Kuala Lumpur. I’ll get to spend a day or day exploring the city, and then head on to Nepal.

This route is far more time-intensive but does appear to be paying dividends.

My estimated cost going this route: $2,000 – $3,000


I picked booking a series of individual one-way flights, and that’s giving me a ton of flexibility in case something happens. My current plan is to have flights booked so I have flights out of whichever country I’m flying in to. Thus, I have my flight to the Philippines booked, my flights through the islands, and my flight to Cambodia. That’s it. We’ll see what happens next!

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