How to travel like you can’t afford it.

Taylor and I have managed to do a lot of traveling. Enough so that our friends are always asking us how we make it work. Even now, as I wrap up the fourth week of a rural psychiatry rotation in Southern Oregon, we’re planning the final details for flying to Japan next week.

I think travel is pretty awesome. It expands your world. It expands your comfort zone. It brings you in touch with people and cultures that expand your appreciation for the human race. In the interest of persuading you to travel like we do, if only once, I’ve compiled a list of tips, hacks, and philosophies that make it possible to put together amazing travel experiences with less money than you’d expect. It’s not definitive, but it works for us. Over and over again.

This adorable hut on the amazing Bomber traverse would never be here on this page if it weren’t for a half-cocked dream turned into reality by unbridled optimism and half-sane planning.

Recognize that it’s possible.

This is crucial. It’s all about the mindset, so we have to start here; You really can create radical travel experiences for yourself that are just as cool and at least five times as real as what you drool over in magazines. It’s critical to know that it’s possible, and once you’ve pulled off one amazing trip that defied your expectations, the drive to make more trips happen will just grow. Just because you’ve never done something like this doesn’t mean that you can’t. When in doubt, remind yourself that the people in the magazine are on some lever just regular jokers like yourself. If they can do it, you can too.

He wasn't having it.
He wasn’t having it. No matter. We were still in Iceland.

Divide the costs.

This is largely psychological, but it’s absolutely key: don’t pay for everything all at once. A year out from your trip, make the big dive and spend the money on flights. Even if you’re not sure how you’re going to pay for the rest of the trip, making the commitment brings the trip into reality and facilitates saving. Six months before you go, book any accommodations that you’re planning on using. Three months out, book a rental car if need be. It’s pretty much impossible for someone making less than $75k a year to spend $2,000 all at once, but it’s psychologically a lot easier to spend $500 four times in a year. Just don’t go into debt for travel, please.

Sun strikes Imogene peak above our camp. We'd have to hurry to get skiing before it warmed up.
Sun strikes Imogene peak above our camp in Idaho’s Sawtooth range. We’d have to hurry to get skiing before it warmed up, but the trek in was worth it.

Take advantage of free money.

Ignore this paragraph if you have trouble managing your money, struggle with credit cards, or if you already have a lot of debt that you can’t pay off (check out the next section instead). For the rest of you, I say to you that if you’re not taking advantage of a travel credit card, then you’re losing out. Lots of credit cards have benefits, but they tend to be pretty limited. An REI credit card sounds great until you don’t want anything at REI but would rather actually go outside. A cash-back card is nice, but you’ll actually get more money back if you opt not for cash, but for a cash-surrogate like miles or points.

But points are a pain! You have to schedule flights through lame airline websites, they seem worthless at times, and you can never do what you want when you want. Thankfully, there’s a solution. For those with reasonable credit, there are credit cards that let you spend your acquired points on any travel. That means that you can pay with credit for rental cars, Airbnbs, or any flight that you want, and afterwards you can redeem points for a statement credit. Limits begone.

I recommend the Barclay Arrival Plus World Mastercard, and it’s what I use to pay for a lot of my travel. I also run as many expenses as I can through the card. Lots of utilities bills and other regular expenses offer the option to pay by credit card. If there’s no fee, then do it! Every dollar that you pass through the card is a free point to spend on travel. Of course, this is a waste of your money if you don’t pay off your credit card completely every month. Screw up once or twice and you’ll waste all of the benefit that you’ve derived from the card. But pay it back always and you get free money.

Barclay Arrival Plus World Mastercard

Chase Sapphire Preferred Visa

Along the road, Bruneau Dunes State Park, ID
Along the road, Bruneau Dunes State Park, ID

Save money you didn’t know that you had.

Slowly accumulating savings for travel has never been easier, thanks to tech. A number of apps have cropped up in the last few years that help you to save towards a goal by rounding up transactions on your credit or debit card to the nearest dollar. The automation makes it very behaviorally simple to save money, which can otherwise be a bit painful. Over the course of a year you can sneakily save $300-400 without feeling like you’re going without your daily coffee. That money could be a round trip ticket within the continent, or it’s enough to really amp your budget on a two-week trip.



Cottonwoods and Water, Coyote Gulch, UT
Cottonwoods and Water, Coyote Gulch, UT

Be flexible with your travel plans.

Or be crazier than everyone else. The most expensive times to travel are when everyone else wants to.  The most expensive times are also when a travel destination is in peak season; think Iceland in Summer, or Whistler in the Winter. If you have the flexibility to travel outside of holiday periods, or if you’re crazy enough to travel off-season, the cost of a flight can be less than half of what it otherwise would be. In this way, it helps to be a skier– when the weather is foul and the tourists are away, that can be when the skiing is best.

-Avoid holidays and academic breaks.

-Fly on Monday-Thursday.

-Fly at odd hours.

-Fly in the off season.

Our first look at "Wizard Island"
Winter is a great time to go to National Parks. It keeps the riffraff away. (Wizard Island, Crater Lake NP)

Buy cheap flights.

‘Duh!’ you say, ‘of course I want to buy cheap flights, but they don’t really exist’. I’m going to let you in on a secret. This requires a lot of flexibility, a lot of patience, or both, but it has saved us hundreds of dollars on flights in the year that we’ve been using it:

This dude Scott has some kind of notification system worked out to keep a close eye on flights to everywhere, and when prices drop to ridiculous levels, he sends out an email blast. Recent opportunities have included round-trip to Switzerland for $300, Finland for $350, and Beijing for $400. Give Scott the $20/year that he deserves for finding these flights and he’ll send you more and better deals. The catch is that you have to sit and wait and hope that the flight you want will appear. Our honeymoon trip to Paris from Portland took 2-3 months to drift by, but we saved ~$800 by waiting. His quoted average is a savings of ~$600 per flight.

Scott’s Cheap Flights (Free Version)

Scott’s Cheap Flights (Full Version)

Descending into Anchorage over the Chugach.
Descending into Anchorage over the Chugach range.

Don’t use hotels.

Roughing it is best, and Airbnb fills in the rest. Taylor and I went on a 2 month road trip from California to Utah to Colorado to Utah to Idaho, Washington, and British Columbia and we paid for a place to sleep on exactly 2 nights. If you cook for yourself and camp on national forest land, then you save yourself between $15 and $100/night. If you really want to sleep indoors, then look on Airbnb. Hotels are a terrible deal, and they never have a good place to store skis or wash a bike. Most places that you’ll want to travel to ski or ride will have good options on Airbnb, usually at half the cost of a hotel and sometimes including meals, locals secrets, or a bike wash. Taylor will filet me for throwing this out there, but if you’re looking in an obscure european country and not finding what you want on Airbnb, take a look at, as they’re better known in Europe. It’s just not as good a deal.

National Forest Locator Map


Best of all options: stay with friends. It’s best to have friends who are care taking remote mountain villages for the winter. Photo: Peter Innes


There you have it. The only step that we skipped was the dreaming and scheming, which is a whole ‘nother post to write. Pro tip: keep travel guidebooks by the toilet.

All you need to do is dream a dream, take advantage of all the free money that’s out there, save systematically, and spend strategically. If you do one thing next year, do this for yourself: plan a trip that has always lived in the ‘dream’ category.

Category: Knowledge & Technique



  1. I never heard of that flight website. I will definitely try it when we are off the student schedule! Thanks!

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