Rant: Planning Ahead & Being Spontaneous

If you're traveling to another city, do you plan ahead, researching the restaurants, bars, wine shops, bakeries, and other such places that you want to visit? Or do you prefer to be spontaneous and simply wander around, hoping to find places of interest? I know travelers on both sides of this issue though my own position is closer to a middle ground, trying to avoid the disadvantages of each choice while gaining the benefits of both.

For example, last week I traveled to Chicago, for the first time in over twenty years, for a couple of days with a very good friend. As it was a short trip, I knew we needed to pack as much as possible into our brief time. For me, that entailed researching Chicago, learning the names of some of the most interesting restaurants, bars, and such. With that information, I had a solid foundation for the exploration of Chicago, having located places which appealed to our interests and preferences. Chicago is a very big city so we would never have just stumbled upon all of those places on our own.

We had lots of luck with the places I researched and then visited, from QXY Dumplings, a killer soup dumpling spot, to Motomaro, an amazing Japanese restaurant. And with my preplanning, we were able to set up a restaurant crawl for one evening, dining at three restaurants for dinner, each place about a block or so away from each other. Simply wandering around might not have led us to these three restaurants.

However, some spontaneity and flexibility was warranted as well. We didn't preplan every minute we'd be in Chicago, leaving open time to explore the city. After enjoying a delightful lunch at QXY Dumplings, we wandered around Chinatown and stumbled upon a bakery that sold Pork Belly Cookies! I never saw anything in my researches about those cookies in Chicago. Later, we stopped at a wine & spirits store and received a recommendation to check out a nearby wine bar & restaurant, Income Tax, which turned out to be a very cool spot. And at Income Tax, we received another excellent recommendation, to Estereo, a great bar with plenty of Pisco, Mezcal, Cachaca, Tequila and other similar spirits.

If we had been rigid in our plans, we never would have encountered those spots. And only a balanced approach, of both prior research & planning, mixed with some spontaneity, would have led to the best results. I spoke to someone else who was visiting Chicago at the same time as us, and they were amazed at all the places we had visited, places she knew nothing about. Her own experiences, which seemed based almost entirely on spontaneity without any preplanning, weren't as successful.


We had an amazing time in Chicago, filling both days with lots of incredible food and drink. In the near future, I will be writing much more detail about my travels to Chicago. If you travel, I highly recommend you do your research first, and then ensure you allow time to be spontaneous, to wander around seeing what you might find.