I left for a week-long solo road trip across the Midwest on Christmas Day. I had no work obligations, no set schedule to maintain, and really just had the vision to check a few states off Emily’s bucket list. I’ll be honest, I didn’t do much ahead of time to plan the trip, and I changed course multiple times during the journey as I found things to do or I grew restless. It was the most I’ve ever flown by the seat of my pants in years.

On the second to last day of the trip, I realized I had not determined where to stop for the night. As I reached the Wisconsin-Illinois border, I pulled over at the Welcome Center and started looking at hotel costs for towns about three hours down the road. I couldn’t believe how ill-prepared I was in that moment. But instead of growing upset, I simply looked at the teddy bear in the passenger seat, laughed, and said, “Here’s yet another thing that wouldn’t be happening right now if Emily were here.”

Emily Made The Plans

Usually, I thrive on very set plans because I feel safe when I know what to expect. I need to know where I’m going, when, and who will be there so I can plan out what to wear, how to act, and what coping skills I may need to handle the situation. Without a plan, I often feel on edge and scared, which can make me act in ways that are really quite unbecoming.

Emily knew about my anxiety issues and a need for clear plans before we even started dating. She often tried her best to accommodate my need for structure whenever we made plans. Regarding vacations specifically, Emily absolutely loved to plan out every detail of our trips and vacations, so I usually let her handle all of that while I handled other things, like booking flights or preparing the car for a multi-hour journey. It was our system, and it worked.

We Went to St. Louis

I remember one of the first trips we ever planned together was to St. Louis. We had originally slated the trip for March, 2021 (before we started dating). However, I had some conflicts come up, and we moved the trip to September. Looking back, this ended up working in our favor because we were fairly settled in our relationship by the time we went, and this opened the door to some things that probably wouldn’t have been the same if we hadn’t been a couple at the time (like our “special cave time” in the City Museum… but that’s a whole other blog post).

When we started discussing the trip, Emily told me she’d plan everything out. However, I didn’t realize just how detailed she was until a few weeks before the trip. Essentially, Emily had a list of activities, the costs, and about how long it would take to do each one. She then planned out the entire three-day trip, with contingency plans based on weather or other factors. She also had a list of optional extras we could do if we had extra time. It was the most elaborate trip planning I’d ever seen. It made me laugh, but I also loved it.

Throughout the course of the three days we were there, we checked pretty much everything off the list. We went to IKEA, enjoyed tons of local food, walked through the entire St. Louis Zoo, explored a huge park and a science center, and went to the City Museum. Although we were flexible with timeframes, I really liked how Emily planned everything out.

A Knack For Finding Things Off The Beaten Path

One of my favorite things about the trips that Emily planned was that she’d always sneak something completely unique into the trip. For example, when we went to Chicago, we did a lot of the typical Chicago things. But Emily also picked out two things that were very random and very Emily, one of them being our visit to Hull House.

Unless you’re a nerd like us, you’ve probably never even heard of Hull House. The house was founded by Jane Addams, who is often called “the mother of social work.” The compound was a place to help immigrants and underprivileged people in Chicago obtain housing, medical care, and more. The entire museum was fascinating, and we even learned that the federal government investigated Jane Addams because she was “dangerous” due to her liberal views and likely a lesbian.

When we went to Melbourne, Florida, Emily found an adorable breakfast place we checked out one morning. It was clearly a staple for the locals, even though from the road you’d easily ignore it since it was one of those “hole in the wall” places. Again, I don’t know how she found these places, but she always did and it was always great.

She Didn’t Just Plan Destinations

With almost every trip we went on as a couple, Emily made these highly detailed plans. She even did it for our trip to Florida this August and went so far as to plan what we would eat each day so she could grocery shop once we arrived. I don’t know how she could work out all the logistics and find so many fun things to do, but she did.

Also, she didn’t just plan things to do. She also researched medical facilities in the area and had everything planned out in case either of us had a medical emergency while we traveled. I know this was primarily because of her own medical history, but it still made me laugh. She was so detailed and methodical with everything.

She’d always bring along a small notebook and would make sure I knew exactly where to take her if she had any issues with her heart of anything else while we were on the trip. Of course, we never needed any of the facilities she researched, but for Emily, this was just another part of the planning process.

I Can’t Plan Like Emily

I went into my Midwest adventure with virtually zero plans and made things up as I went along. Part of this was because, to be brutally honest, I wasn’t sure if I’d even make the trip at all. Also, I didn’t want to have set plans because the weather and my mood are both fairly unpredictable. So, I just sort of went with a general idea of towns I’d hit, and I decided to plan the rest as I went.

In reality, there’s no way I can plan trips the way Emily did. She just had a gift for researching, mapping itineraries, and finding hidden gems in every city. I didn’t even want to try being her this way, so I opted to go in the opposite direction. I’m sure it drove her nuts a couple of times (especially on the night when I opted to get high and watch five episodes of The Crown while eating cheese instead of going out and exploring), but it just felt like the right way to approach my first trip without my travel companion by my side.

Because of Emily, I enjoyed several amazing vacations and road trips throughout 2021 and 2022. I don’t think trips will ever be the same without her now. However, I also know that she’d kill me if I never went on vacation again because traveling was a love we both shared.