cheap travel

Cheap Travel: Tips, Tricks and Cheap Destinations

Cheap travel is more accessible than you might think.

For most of my career, I’ve been in a position where I interview and hire people for our company. I’ve interviewed thousands of candidates and hired hundreds of them. You learn a few things when you have that many conversations focused on the same topics.

I like to make my interviews feel like conversations instead of inquisitions. It’s more comfortable for the candidates and I learn more about them when they are put at ease.

One of my standard interview questions:

“If you awoke tomorrow morning and you had all the money you would need for the rest of your life, what would you do with your time?”

What do you think is the answer 90%+ of the time?


I’m being a little sneaky when I ask that question. Because I already KNOW most people are going to say “travel,” I’m ready with a follow-up question. The answer to the follow-up question is what I’m after.

After the candidate answers, “Travel,” I respond with, “That’s great! Where would you go first?”

I get all sorts of answers to the follow-up question, but every answer falls into one of two categories. Either the candidate is very specific and starts rattling off places they have clearly researched OR the candidate speaks in vague terms and doesn’t have any specific destination or reasoning behind the idea of “travel.”

The idea that traveling is reserved for wealthy people is a myth. Cheap travel is easier than ever thanks to the internet. You can research destinations and book travel accommodations on your iPhone in-between bites of sandwich during your lunch break.

In fact, there are plenty of destinations that will cost far less than you’re paying to live in a typical US city.

That’s right, you can SAVE money by going on vacation.

For a recent example of some cheap travel, I took a trip to Colombia (the country) from San Francisco (where I live). To be fair, San Francisco is one of the most expensive cities in the US, but bear with me.

A one-bedroom apartment in San Francisco costs about $3200 a month right now. That’s for roughly 550 square feet and doesn’t include parking. Some of the added benefits (haha) of living in San Francisco are a hefty sales tax (8.5%), the highest state income tax rate in the US (up to 13%) and the fact that you pay a premium for things like groceries (priced 20-30% higher than anywhere else in the US).

But the weather! Lol

To get to Colombia, I bought a round-trip plane ticket for ~$500 and booked an Airbnb in a nice part of Medellín. The Airbnb was a one-bedroom apartment that cost me $24 a night. It was a lovely place and very comfortable.

So, a month of living in an apartment in Medellín would cost me $744 plus a $500 plane ticket while a month of living in an apartment in San Francisco would cost me $3200 (plus utilities and parking, so another $200-$400 a month).

Things that make you go hmmmmm.

Uber has a presence in Medellín and it cost me $3-5 per ride to Uber just about anywhere I needed to go. There’s also a train system that is far superior to the public transportation options in San Francisco and that cost me $.90 per ride.

The costs of housing and transportation were wonderful, and everything else in Medellín is inexpensive as well. I tried my hardest to break the $20 barrier for a nice dinner in Medellín and I couldn’t do it. I would get the most expensive steak on the menu, wine, etc. and I couldn’t spend more than $20. It was glorious.

Update: My new expat friends in Colombia have informed me of a few restaurants where I can definitely spend more than $20 on dinner. I’ll give those a try on my next trip and report back.

Cheap travel is here to stay. The world is rapidly adapting to the idea of a distributed workforce as it becomes easier to do many jobs from anywhere that has wifi.


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