How I Travel for (Almost) Free

I’ve been traveling a lot lately – 30 countries and 11 states in the past 2 years – and my friends and family keep asking how and why.

“Are you really a secret agent working for the CIA?”

“Did you win the lotto?”

If I was a secret agent I wouldn’t tell you. And no, I didn’t win the lotto. But by using some simple travel hacking techniques that involve strategically using credit card offers, manufactured spending, and knowing the ins and outs of airline loyalty programs, I’ve been able to collect over 1 million miles in the past 2 years very inexpensively and with little effort.

This is called travel hacking, and there are many blogs you can follow to learn more about it. And I’m telling you that travel hacking works. It can help you a great deal if you’re willing to put in a small amount of time and effort.

I’ve flown for almost free (excluding taxes and fees) for the past 2 years and some of this has been in first class. If you can remove the cost of flights from your trips, travel can be much more affordable or open up other travel-related opportunities. I’ve also been lucky enough to take advantage of some really good mistake fares – I flew to Abu Dhabi for $187 round trip, to Los Angeles for $210 in first class, and next year I’ll go to Dublin on a ticket that costs only $99.

Much of this is not vacation – it is travel, and there is a big difference. This quote by Anthony Bourdain sums it up nicely:

Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s okay. The journey changes you; it should change you. It leaves marks on your memory, on your consciousness, on your heart, and on your body. You take something with you. Hopefully, you leave something good behind.

I don’t know many people that like to travel how I travel. Sometimes it is not very relaxing. I’m constantly on the go. Sometimes I like to do things the hard way. Sometimes I don’t sleep much. I’ll do things like taking longer flights with more connections to do a “mileage run” to rack up miles.

But overall I want to have the most authentic experience as possible. This means that I don’t stay in fancy hotels or eat at expensive tourist restaurants. I generally book places on airbnb where I can stay with and connect with locals to find the off the beaten path places. And while I’m away I rent out my own home on airbnb to recoup my travel costs.

In Jordan I camped out in the desert with a Bedouin family and in Cuba I stayed with a local family in a “casa particular” – some truly unforgettable experiences I would have not had if I stayed in hotels.

The Bedouin camp in Jordanian desert.
The Bedouin camp in the Jordanian desert – middle of nowhere.


The classic cars and architecture of Cuba make you feel like to stepped back in time.
The classic cars and architecture of Cuba make you feel like to stepped back in time.


No matter if the trip is 4 days or 4 weeks, I never check a bag. I can fit all I need, including an 11-inch macbook, into a 48 liter carry on backpack.

Lastly, I work while I travel. The photos may show otherwise, but I work a lot on extended trips. I have a new job, new responsibilities, many ongoing research and creative projects. I have to carve out time to get work done while I’m away.

90% of the time I travel by myself, but I have some solid strategies for meeting people so making new connections has been easy (and perhaps opens up opportunities to visit again in the future).

Even if this isn’t your style of travel, knowing a little bit about travel hacking can help you get more out of your travels.

Here are some of the most recent places I have been, but follow me on Instagram for more travel photos: