Take an Unplanned Vacation

Today I woke up in Mesa, Arizona, went for a quick swim, ate remarkably-accurate New York-style pizza in a Southwestern town with a population of around 200, drove to the Grand Canyon, slipped on my Vibram Five Fingers and hiked a bit, slowly made my way to a Route 66 town called Williams where I downed a Blue Moon, listened to some live, twangy oldies music (sung by a mountain man), then watched Jurassic Park while relaxing in a cheapish hotel room with too many beds.

Being able to do this on a Monday must be the product of a lot of planning, right?

Nay, good sir/madam. In fact, my girlfriend and I were vaguely planning on taking a trip to the Grand Canyon sometime before we go our separate ways at the end of August, but we definitely were not planning on doing it today, nor were we planning on leaving LA this weekend, much less stopping in Williams, Arizona for the night (and we definitely were not planning on watching Jurassic Park).

We took an unplanned vacation.

The unplanned vacation is a temperamental and flighty beast, especially for someone like me who can enjoy rolling with the punches, but definitely tends to plan everything if given the opportunity.

The rules for such an outing are three-fold, as are the benefits.


  1. You cannot make ANY plans with absolute certainty. No calling ahead for hotels, no buying tickets online any sooner than a few hours beforehand, no telling friends for weeks ahead of time where you’ll be (you shouldn’t know where you’ll be at that point, anyway, or that you’re even taking the trip). The whole idea is to maintain your potential for spontaneity, which is not something we’re allowed to do in real life very often.
  2. Make an effort to do things that you wouldn’t normally do. Sure, that Starbucks might be a little cleaner and has familiar sizing conventions for the cups and names for the specialty drinks, but that Mom and Pop coffeeshop down the road will almost certainly have a whole lot more character, put a lot more effort into making sure you’re happy (they are competing with that Strabucks, remember), and might have drinks and pastries you’ve never even heard of (yum!).
  3. Bring only what you need for three or four days, but leave your options open. If you find that you’re ready to head home after one night, do so. If you want to stay out a whole week, make it happen. This rule may not be quite so easy for people with strict working days and hours, but do what you can within the time that’s available. Even a 3-day weekend can be plenty of time if you do it right.


  1. Not making any set plans will allow you to act spontaneously and really be in the moment. Ever been on a really stressful vacation or trip? Most of the time, this stress arises because of plans not going the way they were supposed to (or the fear that they won’t). If you pre-purchase tickets, you HAVE to be there for the opera/burro ride/spaghetti western or you lose your money with nothing to show for it, and that would be a shame. The even greater shame is that planning like that only takes your vacation and imbues it with the same scheduled-feeling of work, the very thing you are trying to avoid for a bit. Don’t do it.
  2. Going out of your way to try new and interesting things is almost always a fantastic experience, and if it’s not, well, that can be super-fun, too. A lot of my favorite moments while traveling have been while visiting highway-adjacent sideshow attractions (World’s Biggest Ball of Twine, World’s Saltiest Peanut, etc) that have just been really godawful. Taking photos, joking around with friends, and generally not taking anything too seriously can be a blast, however, and these kinds of adventures-gone-wrong are catalysts for that kind of attitude. Plus, it’s always good to expose yourself to new things. Learning is cool, kids.
  3. Bringing only what’s necessary is key to keeping your stress level down. While preparing (at the very last minute, of course) for this adventure I’m currently on, I packed a pair of nice shoes, a nice shirt and a suit jacket (in case we decided to head someplace fancy), my Five Fingers (very versatile shoes, which came in super-handy at the Grand Canyon, but were included for running while on the trip…multi-purpose clothing is great for packing light), a pair of workout shorts/swim trunks (quick-dry, moisture-wicking material for swimming or sweating), a few t-shirts, a nice pair of jeans, my toothbrush/toothpaste, contact lens solution/case, and my trusty laptop (in case a client called me with an emergency). It all fit into an overnight bag, and it’s wonderful to have so little to worry about.

The whole concept is so simple, yet also very much against our ‘vacation response,’ which usually leads us to overplan. Because of this tendency, most people will never do something this spontaneous in their entire lives, and it seems like they have a valid reason not to: it can be a lot cheaper and quite comforting to plan your trip ahead of time. It removes the need to think! The trade off, though, is that you miss out on those novel experiences and have to follow the schedule from beginning to end. Funnnnnn(?).

When it comes to stress-relief, nothing beats getting away from your typical environment and having no place you have to be. Despite the 10+ hour trip driving through a fairly barren desert on the way here (we decided to hit up Phoenix yesterday last-minute in order to visit an old friend, so it took a little longer than a straight-shot from LA would), my shoulders and back feel looser and less tense than they have in over a year.

Further, taking this kind of trip allows you to be in the moment and take in your surroundings like nothing else. Since you don’t have a definite end-destination in mind, you’ll be watching every town as you drive by – both small and large – for fun stuff to do. When you have a set destination, on the other hand, these potentially fun things remain nothing but billboards on the other side of your car window.

Last, but certainly not least, these kinds of trips can be SUPER cheap. I’m not strictly adhering to this rule on my current trip, but I find that knowing how much you’re going to spend ahead of time (I know, I know, it’s like planning; but it will be based on how much you can afford to spend, not what you will be doing, so it’s allowed) and taking out that much in cash can be a good way to keep track of your budget. Get enough smaller bills to use on the road without attracting the wrong kind of interest and you’re set. You’ll know when you should start heading home and which activities to choose from your myriad options based on how much legal tender you have left in your pocket.

If done right, this kind of trip can be the ultimate de-stressor. Have you taken an unplanned vacation before? What did you end up doing? Have any additional tips, rules or benefits to add? Share with the rest of us in the comments below!

Update: May 9, 2016

I think this might be the first time I ever acknowledged the benefits of being prepared for anything as a person in contrast to being prepared for a very specific set of things because of thorough planning.

It’s difficult to remember what I must have been like back then, as ‘rolling with the punches’ has become so second-nature that the rigidity of a set schedule seems downright confining. That’s not to say that there isn’t a degree of planning involved with how one packs, and in which direction one chooses to go, but to plan much more than that and really get into the specifics leaves out a lot of what I enjoy about travel.

I’d forgotten about this trip till just now, which is a shame. My ex and I had a blast, and it was a mental salve that made me think that this full-time travel thing I was planning might not be such a bad idea after all. I wasn’t seriously doubting the path I’d chosen — I’d committed to it, regardless, so if it proved to be a non-optimal direction, I’d change course and figure out something new — but I had no idea how doable it would prove to be once the rubber hit the road. Up until I left, it was all just theory. This little trip showed me a little of what I could expect, and I loved it.

It’s important to note that those little Five Finger shoes were all the rage in the lifehacking community back then. We were all so proud of ourselves for having discovered this bizarre new product before everyone else.