Bad choices. Good times.
How “always wrong” is “just right” when we travel.
My wife and I try to visit new cities as often as we can. We love the idea of experiencing a place — the food, the music, the nightlife — for the first time. The problem is, we’re awful at it. Whether it’s Savannah or Boston or Vail, we find a way to do every single thing wrong, every single time.
However, despite these colossally bone-headed choices, we still manage to have a great time. What’s our secret? Let’s use our latest trip to Austin to answer that question.
Step #1: Do NOT research anything.
Even with all the information in the world just a click away, we tend to do very little research (READ: ZERO) before a trip. Why? Mostly because we’re not that bright. In Austin, that meant booking a hotel miles from anything of interest. Sure that sounds bad, but…
Step #2: Walk, then walk some more, then keep walking.
At home in Chicago, we take Uber (sorry, Austin) or cabs everywhere. When we’re feeling thrifty, we take public transportation. On vacation, we walk everywhere…with little regard for the distance or the damage it will do to our bodies. Boston? We walked the ENTIRE Freedom Trail in one day. Savannah? We started our trip walking the wrong way for miles, then turned around and walked the right way for many more.
Austin? We decided to travel from our hotel to South Congress on foot (I was in flip-flops to add a new level of stupidity), knowing full well that it was a 2.5 mile stroll in near 90 degree heat. Yay, new fitbit record!
Step #3: Just pick places at random.
Recommendations from friends and coworkers? Pffft. Yelp? Never. The best way to find interesting places in a new city is to just pick them randomly. No looking at the menu outside either. That’s cheating.
In Austin, this was almost our first stop on day one:
Sadly, the wife shot that one down (it might have been the hostess in a bikini, but we’ll never know for sure). On day two, we ended up at Perla’s. Which we found out was an oyster bar only after ordering a drink. This lead to our first (and last) order of oysters. Or as we now call them: slime boogers.
Step #4: Embrace your errors.
But, here’s the thing about all these “mistakes.” They almost always lead to great memories. In Savannah, we found a pirate-themed bar and a woman there, while dressed in full swash-buckling gear, regaled us with tales of the buccaneers that used to call the city home. In Boston, we were yelled at by a surly bartender with the what can only be described as greater New England’s thickest accent simply for daring to ask about drink specials.
In Austin, we were greeted by a homeless man’s penis within the first hour of arriving and were later chased down the street by a screaming man pushing another guy in a wheelchair he didn’t appear to know.
Ok, so maybe they don’t ALL lead to great memories. Unwashed genitals aside, all our best travel stories start with or are shaped in some way by being terrible at traveling. I, for one, can’t wait until our next trip.
Hey, I’m Jason, a senior copywriter at Simple Truth. If you ever want truly terrible tips, send your tweets to @fiveoutstogo.
