Travel Hacking Basics

Before we begin, let’s just lay our cards out on the table. Jason and I are not travel hacking experts. We’re not even intermediate travel hackers. And when you look at the people who know their stuff, we’re really in the minor leagues. We know about as much about travel hacking as college freshman do about the real world. If you’re looking for professional advice on the subject, click any of those links.

That said, Jason and I have picked up a few tips. We started our trip in February of 2010 when we put all of our possessions except for two suitcases worth of stuff into storage and high-tailed it to Australia for four months. Then we came back to Virginia for a month, then to Chicago for four (where we picked up our dog who was lovingly being cared for by friends) then moved to Austin, Texas for what’s now been 6 weeks. After Texas, we’re planning to hit Brazil for a while then move somewhere out west, but we’re not really sure where yet. Part of the adventure is going where the wind takes you. Thus far, we’ve been living out of two suitcases each for more than a year now. Our plan is to continue traveling for at least two years, maybe more. For right now, our lives are possession-light, experience-heavy and I’m pretty sure we wouldn’t have it any other way.

The question I get asked, fairly frequently, is “are you rich?” Ha! No! Far from it. We aren’t rich. We aren’t even moderately rich. We just happen to have mobile jobs, we travel slowly so we can work at each place we stop without feeling like we’re missing out and we have flexible schedules, so we can take advantage of things like cheaper airline tickets, free museum days and happy hour specials.

That said, here are a few guidelines on what makes our lives affordable:

#1: We work hard and love what we do.
We go out a couple nights a week, but whenever we’re home, we’re working. It’s constant and if we didn’t love what we respectively do, we would kill ourselves, each other and anyone that happened to be nearby. One of my goals in 2011 is to work smarter, but until that happens, I don’t think that the way we live would be possible if both of us didn’t absolutely love what we do.

#2: Travel slow
Jason and I generally don’t go anywhere, besides the occasional weekend excursion, unless we can stay for at least 3 months. That’s because it’s easier for us to move somewhere for 3 months, working the whole time, than it is to take an entire week off of work to travel. Instead of cramming our trips into two weeks of solid vacation time, we stay for a while, work during the day then explore at night and on weekends. Traveling slowly has a couple of bonuses. First and foremost, you can pay rent instead of a nightly hotel fee, you can plan your trip around the cheapest prices and you won’t get burned out as easily. Also, for us, it’s easier on the dog. Your two biggest expenses are going to be where you stay and transportation to get there. Here’s how we deal with those two obstacles:

#3: Forget hotels.
Unless you take baths in money and have servants wash your nether-regions, hotels are out. On our budget, couch surfing and house sitting are an option, but we mainly rely on Airbnb. Through Airbnb, anyone with any amount of free space—whether it be a spare couch in their heated garage or a palace in their backyard—can rent out their place for the day, week, month or year. I cannot underscore how much this site has changed our lives. In addition to offering everything from an igloo in Slovenia to a castle in Britain, the site is also substantially cheaper than almost anywhere else we’ve found. Jason and I found the four bedroom house we’re currently living in at the same price we paid for one room in Chicago. To maintain some sort of financial consistency, we have a budget range regardless of where we live. We simply alter the amount of space we can get from place to place. That way, we are essentially staying somewhere new for the same price that we would pay to stay home.

#4: Think outside of the brands
Big sites like Orbitz will give you (sometimes) decent airline prices, but airlines that aren’t on big box aggregator sites have better deals. Baker of Man Vs. Debt has a step-by-step guide to finding insanely low airline prices.

#5: Use rewards
We’re just starting to get into this and it would be a crime not to direct you to Chris Guillebeau’s site right away. That guy is the Mr. Miyagi of rewards travel. It’s easy to fall down the slippery slope of frequent flier miles. People make full-time jobs out of staying on top of deals and mileage contests. For now, Jason and I do it much more simply. I have a credit card with frequent flier rewards. We charge everything and pay it off immediately. We also keep an eye out for companies handing out frequent flier points for taking surveys or testing products. There are quite a few sites out there that profile those things, but I really just keep an eye on Frugal Travel Guy and Free Frequent Flier Miles.

#6. Connect With People
Whenever Jason and I have decided that we’re moving somewhere new, we e-mail all of our friends and ask them to put us in touch with their friends. From just sending out that one quick e-mail saying “hey! This is where we’re going to be! Make us friends!” we’ve gotten some amazing experiences including an invitation to the first performance ever to feature Sydney Gay and Lesbian Choir and the Australian Royal Navy band, tickets to a show at the Sydney Opera House, a gangster-themed New Year’s party in the Texas suburbs and eaten at hole-in-the-wall joints we never would have found on our own. Know this – meeting friends of friends is awkward. For someone as socially clumsy as me, it’s horribly awkward. The last time we had one, I got super nervous and ended up talking extensively about the extraordinarily perverse mating habits of bees. Here’s what I learned from that experience – nothing, NOTHING will repel new people quite like the phrase “Bee-Gina.” Regardless of the awkwardness, press on! Knowing someone in town who can advise you on where to go on the cheap is invaluable, even if you have to go through a few sweaty-palmed first friend dates to get comfortable.

If you guys have any AMAZING tips that have worked wonders, by all means, leave a comment or shoot us an e-mail. We’d love to hear them.

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3 Responses to Travel Hacking Basics

  1. diana says:

    I have no tips, but I will definitely be using some of yours! This sounds like an awesome way to actually get to know different places!

  2. Billy says:

    Great article! Loved it….. On my way to Guillebeau’s and Airbnb

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