Intro to Travel Hacking

Traveling has been on my mind a lot lately.

I’m in my final days in Boulder, heading back to San Diego on Sunday.
I’m a little mixed, there are so many things I love about Colorado, and Boulder, but I’m also really looking forward to getting back to the coast.

And on October 15th, I’ll be boarding a plane at LAX to head to Bangkok for another adventure!


I’m starting to enjoy this process. Every time I seem to be able to throw out a garbage bag full of clothes, more books, and more odds and ends that are just weighing me down. I’ve got this thing down to about 3 boxes full of stuff, plus clothes and a couple stacks of files (which I will soon be scanning and saving to my hard drive instead of lugging these papers around!)..

But the plans keep rolling on. After a few days in Bangkok, I’m off to Chiang Mai for an unknown amount of time. I plan to get a cheap place there and work Mon-Friday, and see some new places on the weekends. Myanmar (Burma), and Laos are on the list.

And in the winter I’m wanting to get down to Mexico and maybe further south. I’ve never been to the real Mexico, and I’m hearing great things about Puerto Vallarta as a place to live from Jake at The Voluntary Life!

So I’m sort of a beginner at the travel hacking thing but I’m learning and wanted to share some of the things I’m doing to get more airline points (and hotel points).

I’m flying coach to Thailand this time around but my goal is to only fly business class or better from now on for the longer flights. Here’s what I’m doing so far to accumulate points and miles:

Credit cards, the foundation of travel hacking. I’m not sure how you can hack travel without doing the credit card points thing. It’s ill-advised if you are already in credit card debt, but if you can handle it, you’ll get some nice perks! Here’s what I have so far:

1. Chase Ink Business Card. With this one, you get 50,000 bonus points that can be used on a variety of airlines, including United- but you need to spend $5000 in 3 months. For me, this was easy as I’ve been using this for ALL business expenses. And I run a lot of Facebook ads, so this was a no-brainer. You also get 5x points for purchases at office supply stores (I bought a $300 computer at Office Depot this year and got 1500 points!), and 2x points at gas stations (more on this below) and booking direct with hotels. The first year is free for this card, then it goes up to $95 a year. Worth it, from what I can see.

2. United Explorer Card. 30,000 points for spending $1000 in 3 months. 2x points at gas stations. 2 free passes to visit their lounge. I used this as my personal card and easily hit the minimum spend mark. I just charge all my everyday expenses on it. Groceries, meals out, gas, etc. Goes directly to my United mileage account.

3. Starwood Preferred Amex Card. 10,000 points for making your first purchase. Another 25,000 points for spending $5000 in 6 months. I’m shifting my spending to this card to meet the minimum. I need to start getting hotel points! Other benefits include 5x points for booking any Starwood hotel. You can also transfer these points to many airlines, including United.

The next thing I have just scraped the iceberg on is using reload cards to pay bills. Basically, you can get these Vanilla Reload cards at some gas stations, and put up to $500 on them using a credit card (preferably one that gives you 2x points at gas stations!). Then you can load an Amex Bluebird debit card with these funds, withdraw the cash at an ATM, and deposit it into your account and use it to pay your rent, mortgage, bills, whatever! It’s an awesome system.

However, it’s ridiculously hard to find the VR cards, and when you do, there are often issues. I tried the other day and the machine to load the cards was broken. Then I tried at another gas station and they wouldn’t let me use my credit card. So this scheme is still a work in progress!

So I’m working on improving my systems here, but this is a start and hopefully gives you some ideas on how to hack some of the expenses that go along with world travel.

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Kevin Koskella

Kevin is a podcaster and writer on living free, despite the crazy world we live in. Kevin travels full time and explores the world and how to achieve and maximize freedom in life.

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