I’ve advocated before for getting lost when you travel.
But you don’t necessarily need to get lost to stray from the path or wander off-plan.
When I headed to Chicago for a long weekend with a friend from college, we had a rough idea of what we wanted to do. But, from the minute we arrived in the Windy City, our plans changed.
Originally, our plan for Friday evening had been to eat some deep-dish pizza and then go see an improv show. But when the line at Gino’s East stretched around a corner, we decided to scrap the plan and go visit our friend Heather — who works at the John Hancock Observatory — instead.
Thus began what we dubbed as “The Weekend of Whatever.”
I’ll admit that I’m a researcher and planner when it comes to traveling. I like to do my homework and know all about the different activities that a city or country has to offer. Before I arrive somewhere, I like to know where I’m staying, what the weather might be like, and what I might like to do while there.
But, when it comes to travel, very little usually goes according to plan.
So, even though I often leave home with a rough plan in my head, it usually gets amended or completely thrown out once the travel actually commences.
And that’s okay.
I’m not the type to freak out when things don’t work out, or when plans have to change. In fact, adapting to the situation at hand is one of my favorite things about travel. And, since I’m usually equipped with a knowledge of alternate things to do when something falls through, I’m able to adapt well while on the road.
In Chicago, my friend and I decided to just go with the flow. We decided to let our feet wander and to let our curiosity take over.
And, as experience has proven in the past, straying from the plan was the best plan we could have come up with.
Because we weren’t confined to any sort of schedule, and because decisions and invitations were often met with a “whatever” or a “sure, why not?”, we stumbled upon plenty of interesting things around Chicago.
Not only did we wander around the theater district and along the river, but we also found our way into a Garrett Popcorn Shop, where (at Heather’s insistence) we bought a bag of their famous “Chicago Mix” popcorn.
The “Chicago Mix” is a blend of cheesy popcorn and caramel corn. It may not sound very appealing, but take my word for it that it is absolutely delicious. Oprah even added it to her list of “favorite things” in 2010, so you know it must be good.
We wandered down to Millennium Park, where we had fun taking photos of “The Bean,” checked out the Jay Pritzker concert pavilion, and took a stroll along the BP Bridge.
And then we ran into an a cappella group performing pop songs near the Cloud Gate. They were eventually joined by a passing dance troupe for an impromptu performance of Cee Lo Green’s “Forget You.”
We also wandered down near the shore of Lake Michigan to check out the iconic Buckingham Fountain, even though it was silent and dry at this time of year.
On our way, though, we stumbled upon an anti-war protest taking place.
None of these extras had been in “the plan.” But each one only enhanced our time in Chicago, and made it that much more memorable.
For us, straying from the path paid off.
It’s kind of like the quote that inspired my blog — “It’s a dangerous business, going out your door. You step onto the road, and, if you don’t keep your feet, there’s no telling where you might get swept off to.”
Sometimes, it’s the things we don’t expect to see or do that end up as our fondest travel memories.
So, next time you step out onto the road — no matter where you’re headed — don’t be afraid to lose your feet and wander away from the path.
You might just get swept off to somewhere worth remembering.
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What kind of traveler are you? Do you stick to the plan, or do you like to stray from the path?
I agree and disagree. I agree that some of the best travel moments are those we don’t plan. On the flip side, I don’t always adapt well when my plans are interrupted. I am hypocritical like that!
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Hey, feel free to disagree away! Everybody has a different travel style. And I’ve had quite a few situations of my own where my plans were forced to change and I wasn’t happy about it. But that’s the beauty of travel – everyone does it differently!
I think it’s good to have an idea of what you want to do, but I like things to be somewhat up in the air. I’m a few hours from Chicago myself, and I love taking random trips up there to explore. I don’t know about other cities/countries, but Chicago is definitely a good wandering city. Great pics!
Chicago seems to be a great city to just kind of wander around. I’m sure there are “less savory” parts to it, just like any other big city, but I felt pretty safe just going with the flow and getting lost here and there. Thanks for reading!
I am a seat of the pants guy married to a planner. It actually works out okay. She plans to give her a sense of comfort, but some of our best adventures have happened when we change directions midstream. We also see a lot of cool things because she has done the research and planned. them.
That actually sounds like a really nice balance! And it’s good that you’re both able to adapt and appreciate each others’ travel styles. Sometimes that sort of mixture — of planned and unplanned adventures — is the best.
I pretty much travel the same way that you described. I love to plan and research a trip – not just so I can know what to do, but also because planning a trip gets me excited to take it. But I know things can change, and I’m okay with doing something different once I get on the road.
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Sounds like we’d make great travel buddies, Alouise! I agree that planning a trip helps get me hyped about it. Plus, it’s a great way to get a feel for a place before you visit. I don’t like going into anything completely blind, and travel is no different. But, once I’m in… I’m up for anything!
Wandering around downtown Chicago is definitely a great idea because of all the tourist-y stuff. Hopefully you got to check out lots of other neighborhoods too, because that’s where real Chicago is!
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I didn’t get to check out nearly as much as I would have liked in just 2 days. But I guess that just means I’ll have to go back!
I usually just make a list of things I want to see in a city, arrange them by location, if the city is too big and just set off. If the weather is good, I try to do all the outdoor things first because you never know when the weather is going to turn! Or figure out if something is going to be closed one day and do that asap.
Oddly, I am not much of a wonderer because I like to have some sort of goal, but it may not be in a straight line to get there:-).
I never stress because I know I’ll be back someday!
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And this illustrates the beauty of travel – because everybody does it their own way! It’s great that you don’t stress; I know plenty of people who do!
I like having ideas of both indoor and outdoor things to do, just in case the weather doesn’t cooperate. In Chicago, my backup plan for bad weather was the Museum of Science and Industry. I really wanted to visit, but the weather the weekend I was there was just too nice not to take advantage of!
Coming from Toronto, most of us are so jealous of Chicago, it is so much like Toronto but has managed to do so many more things right – like the waterfront.
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Toronto has city envy about Chicago? I had no idea! But I agree that Chicago has figured out how to do a lot of things right. The metro system, for example. And, yes, the waterfront. And the parks! Millennium Park was very cool. I wanted to check out Navy Pier, too, but never got the chance.
I firmly agree and have written about this myself – I love the road less traveled.
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Sometimes, I think the road less traveled is the road you SHOULD be traveling.
Love the pics! I just saw the movie “Source Code” and recognized “the bean” in your post
Never been to Chicago, but have been wanting to go for a while now. I am a huge planner when it comes to my travel. I like to know what the best spots to see in a city are, what activities one shouldn’t miss, etc. But I agree. The best moments often happened because you veer off plan.
I saw “Source Code” only a couple of weeks after visiting Chicago for the first time, so it was cool to recognize a lot of things from the city!
Thanks for reading, Sabrina!