adventure roulette

I didn’t really know how to approach this. I know a lot of people who’ve said that they’ve wanted to do it, but I didn’t know anyone who actually had.

So, like most things, I made it up as I went along, and sort of made a game out of it. I named it “adventure roulette” (you never know what you’re going to get), and made up rules to go along with it as I woke up early, and set off to the airport at 4am.

Here were my rules (feel free to make your own). I thought they created a decent framework for what I wanted to do.

Adventure Roulette Criteria

  • Any ticket under $500

  • Any destination at least 500 miles away

  • One backpack

  • No input at all from me on the final destination

  • No looking at the ticket until I’m through security (and, ideally, as long as possible)

  • Departure: any time during the day that I show up

  • Return: any time before midnight the following night


Like I said, feel free to come up with your own criteria, but mine gave the agent at least *some* sort of a framework to use to book a ticket without collapsing in a ball of stress because of some oddball request at 4:30am on a Tuesday.

I also realized (and accepted) full and well that I could end up in some field in Idaho, and I was just as prepared to walk around a city all day as I was to hang out in a small little town bar, and make friends with some Idaho ranchers. Everything was fair game.

I made it through security, and to my gate without looking at my ticket. I had about an hour to kill, and when people finally started sitting down around me, I took a look at my ticket.


“And where are you traveling to today, sir?”

“I have no idea.”

*polite laugh*

“Well, let me see your itinerary.”

“I don’t have one. I’m trying something different today. I’d like to go somewhere. I have £500, and I’d like you to book me a ticket.”

“Well, where do you want to go?”

“No place in particular . Whatever sounds good to you would be great!”

“Well,” (getting a little flustered now) “I don’t know what you want to do, so how am I supposed to pick a destination?”

“Literally wherever you pick will be fine. I’m sure of it.”

“Do you want to go to the city? Do you want to go sightseeing? Or what?”

“Whatever you want.”

“What if you hate it?”

“I promise I won’t. I’m sure I’ll have a great experience.”

“Is this a test?”

“Ha! No, this isn’t a test. And, if it was, I’m not sure I’d be allowed to tell you. I just got myself some free time for today, and I want to go on an adventure.”

“Okay then….”

*5 minutes later*

“Well, there you go. That’s £462. Have a good trip, and have a good meal out there. You’re going to...”

“Thanks, Tammy!”


How To Do This Yourself

I had a bunch of people tweet things at me along the lines of “that’s so awesome,” or “I’ve always wanted to do that,” when they found out what I was doing. And the good news is that you can! Here’s how (prepare for underwhelmingly easy directions):

  1. Put away $500.

  2. Go to the airport.

  3. Find an awesome agent. You can tell that some are stressed, and that some are friendly. Talk to the friendly ones if you can – they’re much more fun.

  4. Give them your $500, and tell them, “I’d like you to book me a trip somewhere – anywhere -, preferably a cool place, but it can be anywhere you like for under $500. Can you do that for me?”

It’s really that easy.

The cool thing about this one thing is that I know a surprising amount of people who want to do this. And, while it’s not very hard to do at all in practice, most people won’t simply because of the “unknown” factors involved in booking a last minute trip to somewhere where they may or may not know anyone. Go anyways.

The risk value in this is practically zero. The worst case scenario is that you end up spending more on a hotel and a couple of cab fares than you would like, and that is it. The upside is a whole new adventure that you would have otherwise missed out on.

A few people expressed worry that the TSA or gate agents would give me a hard time if I didn’t have a predetermined destination, but I had absolutely NO issues whatsoever (I only finally found out my destination when I was actually at the boarding gate).

It’s easy to do – all you have to do is go.


Additional travel tips

  1. Show up early, ideally as soon as the ticket desks open. This way, you won’t be *that guy* at the airport holding up a line of 50 people patiently waiting to check in their luggage.

  2. Travel light. Bring as little as possible – ideally just a backpack. This makes it easier to pick any flight, AND it makes your trip that much more fun.

  3. Have fun.

A little adventure every now and then is good for you. If this is something you’ve been wanting to do, and haven’t done yet, just go. There’s nobody stopping you from doing it other than yourself.

And, if you do, hashtag it #adventureroulette, and let me know. I’d love to hear your story of how it goes.