When You Don’t Plan Everything, Everything Goes As Planned


I just took my first real vacation for the first time in two years. I’m used to working, or at least having some obligation, every day of the week—even including evenings and weekends.  It wasn’t healthy. Because of this ridiculous schedule, I would plan out everything the night before, from what clothes I would wear to laying out exactly what I needed to pack for breakfast, lunch and dinner (as I would usually be gone from 8am until 11pm…on good days). People who know me can attest to how crazy it is to see someone pre-assemble the ingredients in a coffee mug and lay out a bowl of dry oatmeal so that their Tasmanian Devil routine in the morning wouldn’t be disrupted. From the time I left my bed until the time I returned, every second of my day was planned.

But during these past 8 days, I again went to ledge and jumped off completely. I allowed my schedule to be dictated by no more than what I felt like doing during that exact second. No alarms, no itinerary, nothing. The only thing I had to be on time for was my flights and even they were so horribly delayed and disrupted that I was truly forced to roll with the punches. How did I do? Surprisingly great. I may have approached melt-down mode once, but I blame that on the Chicago heat wave and a 4am taxi ride for a flight that didn’t leave until Noon…more on that below.

This unplanned but completely perfect vacation will remain one of my most memorable travels. Here are some of my highlights from Chicago to Miami:

It wasn’t even 10am and already 105 deg in Chicago. Breakfast ran late and we thought for sure we’d miss the boat tour. As it happens, the boat tour schedule online wasn’t correct and we got there just in time to board.

Having never really visited Chicago before, I thought this statue of Marilyn Monroe was an everyday fixture downtown. Little did I know just a week or so before visiting, this statue was finally unveiled. It is truly quite amazing. Spoiler alert: she’s wearing underwear underneath.

Taking the boat tour of Chicago wasn’t a planned venture. It was something we saw online and thought would be interesting if time allowed. This experience may have single-handedly made the trip. I fell in love with how the city’s tall, hard buildings so boldly contrasted with the smooth, flat water which weaves between them.

Out on Lake Michigan was one of the most serene moments I’ve had in a long time. You can see the hustle and bustle of the city in one direction, but turn around and it’s just you and the calm, blue water.

Catching a game at Wrigley Field wasn’t at all in the plans. We grabbed breakfast, hopped on a city bus (which is a whole other story involving a screaming homeless man) and bought tickets from a stand outside the stadium. A sunny July day spent watching baseball in Wrigley Field–now that’s American.

I’m by no means an experienced traveler and when flying out of one of the largest airports in the U.S. I didn’t know what was ‘normal’ airport volume. But I feel like this is FAR from normal for 6am in O’Hare. Apparently the record-setting rain in Chicago all fell in one night–8” to be exact. No flights were leaving and even the airport staff was delayed in traffic. That morning Chicago had a new attraction, the O’Hare Zoo.

The view of Biscayne Bay from the balcony made the flight delays, endless lines, sleep deprivation and 11 hours of travel completely worth it. Welcome to Miami…

This was the night we did the “touristy” thing and hit Miami Bayside. A great span of shops, bars and restaurants, but the most memorable part of this evening was the culture. Looking at this photo I can still hear the music and see the locals dancing so effortlessly to the rhythm. I think more people were dancing on the street than they were inside the bar. This city is filled with genuine contentment–a souvenir I got to take home.

South Beach, Miami: the place that has inspired songs, bikinis, diets and soft drinks to be created it its honor. Overall, it was like most public beaches I’ve been too–but who doesn’t love a day at the beach? I was never set on having to spend a day here, but a free ride from the hotel and it just seemed to again work out perfectly.

The night we hit South Beach, we got out of the cab and simply started walking. No plan, no schedule. Walking down the entire strip was pretty amazing. All the restaurants were hustling us for our service, but we chose to eat at “Tap Tap” an authentic Haitian restaurant just a few blocks away from the craziness. In hopes of meeting the rapper Pitbull, we grabbed drinks at the staple of South Beach night life: The Clevelander. No such luck on being star struck, but a perfectly unplanned evening yet again.