A Weekend Getaway to Cincinnati: History, Great Food, and a Little Indoor Skydiving

A Weekend Getaway to Cincinnati: History, Great Food, and a Little Indoor Skydiving

Sometimes the best trips are the ones that do not require a flight, time off work, or months of planning.

For this trip, Cincinnati became the perfect weekend getaway. It was technically a milestone birthday celebration, but more than that, it was a chance for my wife and me to explore a new city, enjoy some time together, and make a few memories without needing to completely disrupt life. That is one of the things I loved most about this trip. Cincinnati is only a two hour drive from us, which made it easy to leave on a Friday after my wife finished teaching, get checked into the hotel, and still have time for a nice dinner that evening.

For two people juggling work, family, and everything else that fills up a calendar, that kind of easy weekend escape is hard to beat.

Staying Downtown at 21c Museum Hotel

We stayed downtown at the 21c Museum Hotel and Spa, which turned out to be part hotel, part art museum, and part reminder that trying something different can make a trip more memorable.

I chose it because it was included in my American Express Platinum hotel benefit, which gave us a $300 rebate, a $100 hotel credit, breakfast, and the possibility of upgrades. We get that benefit twice a year, and this felt like a good opportunity to use it somewhere close to home.

This was our first time staying at a 21c property, and it was unique. There was artwork displayed throughout the hotel, including a couple floors worth of exhibits. It gave the hotel a different feel than a standard downtown stay. Instead of just walking from the lobby to the elevator, we actually wandered around and looked at the art. That is exactly the kind of small thing that makes a trip feel more like an experience.

The Dinner Reservation Battle

Dinner, however, took some effort.

We had heard great things about Jeff Ruby’s Steakhouse, not to be confused with “Jeff Ruby,” which is how our Cincinnati native friend first recommended it. That little wording mix up gave everyone a good laugh, but the recommendation was serious.

The problem was reservations.

Even though I started looking two weeks in advance, there were no reasonable dinner times available. Everything was after 9:15 p.m., which is not exactly our ideal dinner window anymore. I joined waitlists for two Jeff Ruby restaurants through OpenTable, and for the next week or so I kept getting notifications that a table had opened.

Every time I clicked, it was already gone.

Finally, I was able to grab a reservation at The Precinct, which worked out perfectly. It felt like a win before we ever sat down.

The city was especially busy that weekend because the Flying Pig Marathon and the University of Cincinnati graduation were both happening. That probably explains why dinner reservations were so competitive, but honestly, it also gave the city a fun energy.

Underground Beer History and Findlay Market

On Saturday, we did one of our favorite kinds of travel activities: a local history tour. We booked a beer history tour through Viator, and it ended up being one of the highlights of the weekend. The tour took us through underground caverns that were used in the late 1800s to ferment lager beer. I had no idea Cincinnati had this kind of beer history. Apparently, there are upwards of 20 of these underground lagering cellars throughout the city. Many were covered up over time, and official records were lost in a city hall fire, so no one knows exactly where they all are. The one we walked through was not discovered until 2016. That kind of history fascinates us. I love when a tour helps you see a city differently, not just as streets and buildings, but as layers of stories that were almost forgotten.

We also walked through the Findlay Market area, which had a great neighborhood market feel. It is the kind of place where you can wander, snack, people watch, and feel like you are seeing a more local side of the city. After the tour, we had a drink at the brewery, then headed back to the hotel to get ready for our spa appointment. A Spa Visit and a Scottish Pub Dessert

Since we had the hotel credit, we used it toward a couples massage at the spa.

I will be honest, the $100 credit did not go very far for a couples massage, but it helped. And when you are already there celebrating a milestone birthday weekend, it feels a little easier to justify doing something relaxing.

That evening, we kept things simple and went to dinner at the Scottish pub next door. It turned out to be a fun choice. They had a special dessert in honor of Water for Elephants, the musical playing across the street.

It was an elephant ear topped with a scoop of ice cream and caramel drizzle. The best way I can describe it is that it tasted like Cinnamon Toast Crunch in dessert form. Not fancy. Definitely memorable.

Social Darts at Flight Club

Later Saturday night, we checked out Flight Club, a bar with social darts. Think TopGolf, but for darts.

They have different games, electronic scoring, and a setup that makes darts feel more like a group entertainment experience than something tucked in the back corner of a bar. It looked like a lot of fun.

Unfortunately, they were booked, and the next available reservation would have pushed us well past our bedtime. That is one of those moments where your younger self might be disappointed, but your current self says, “Nope, that sounds like tomorrow’s problem.”

Indoor Skydiving Before Heading Home

On Sunday, we had brunch and then headed to iFLY to try indoor skydiving.

Neither of us had ever done anything remotely close to skydiving, and this felt like a fun, safer way to try something new. Supposedly, it feels like freefall, although I have no actual skydiving experience to compare it to. An instructor is in the wind tunnel with you the entire time, which makes it feel much less intimidating. We had all ages in our group, and everyone was able to participate.

Each flight was only two minutes, and that sounds short until you are actually doing it. Two minutes was the right amount of time. We each did two flights, and it was just enough to feel like we had tried something adventurous without completely exhausting ourselves.

Why Cincinnati Worked So Well for a Weekend Getaway

By Sunday afternoon, we were back in the car for the easy two hour drive home. We got home late afternoon, with plenty of time to unpack, relax, and be ready for work on Monday. That might have been the best part.

This trip reminded me that a great getaway does not have to be complicated. It can be a short drive, one good hotel, a hard fought dinner reservation, a history tour, a relaxing spa visit, a ridiculous dessert, and two minutes of flying in a wind tunnel.

Cincinnati gave us exactly what we needed: a fun weekend, a new city to explore, and another reminder that we do not have to wait for the perfect moment to make memories. Sometimes, the perfect moment is just a Friday afternoon, a packed overnight bag, and a two hour drive east.