How I Solo Travel: The Flight

Wondering how I manage to travel so seamlessly? In this post, I share my personal strategies for how I pack, plan, and fly with confidence, so you can too.

How I Solo Travel: The Flight
Photo by Suhyeon Choi / Unsplash

We all plan and execute our solo travels differently. Some of us have whiteboards, some of us use templates, some of us just haphazardly plan on the fly. There’s no right or wrong way. We all have our ways of making this happen. This guide series is meant to explain my process of planning a solo trip from start to finish.


I'll never forget an experience I had flying home from Cleveland. It happened during the summer of 2021 when I was on a Southwest Airlines flight, and I had to make a connection in Baltimore before reaching my final destination. Unfortunately, the connecting flight to Baltimore was completely full, but luckily I had managed to secure a window seat by purchasing the "EarlyBird" option. As the plane started to fill up, my worst fears became a reality. However, it wasn't due to any mechanical or weather issues, but rather the fact that I found myself seated between two large men. Now, I'm not a small person myself, but I usually fit comfortably in an airplane seat and stay within my own space. Unfortunately, that wasn't the case this time. Despite the two men being very nice and trying their best to accommodate everyone, the ride was incredibly uncomfortable for all of us. I don't share this story to instill fear in you, especially if you're about to embark on your first flight. Flying can indeed be anxiety-inducing, but as the famous line from the movie "Forrest Gump" goes, it's like a box of chocolates - you never know what you're going to get. However, once I came to this realization, I started to view flying as just another mode of transportation. In fact, it's the fastest and arguably the safest way to reach your destination. In this guide, I will share my strategies for flying as a solo traveler...in four acts.


Blame It On The Rain

As my vacation time from work approaches, I find myself juggling multiple concerns. Not only am I focused on staying on top of my own work responsibilities and ensuring my colleagues aren't burdened with extra tasks in my absence, but I'm also keeping a close eye on the weather both at home and at my destination. While we can't control the weather, we can certainly plan around it. If you've been following my weekly updates, you'll know that I'm a big advocate for careful planning and preparation. I rely on various weather apps like Accuweather, Fox Weather, and Weather Underground to monitor the conditions and forecasts for my upcoming trip. It may seem like a small detail, but keeping track of the weather can have a significant impact on your travel plans. From deciding what clothes to pack to determining the activities to enjoy at your destination, weather plays a crucial role in shaping your overall experience. I always make sure to plan ahead for my flights. Throughout the year, I ensure that I have Netflix available as a streaming service. It's always handy to have! I download episodes to my iPad of TV series that I'm currently binge-watching, like The Blacklist and Blue Bloods. I also download documentaries, movies, and even some sitcom episodes. Seinfeld is always a reliable choice! Of course, I make sure to keep my selections appropriate for a flight, nothing too racy. This way, I have a backup plan in case the flight doesn't offer in-seat video on demand or live TV.

The Night Before

Checking the weather conditions is crucial not only for planning your activities during the trip but also for deciding what clothes to pack. Since my flight is scheduled for tomorrow, my main focus now is on packing. Since I will be checking in my bag, I usually opt for a larger suitcase to accommodate my clothing, a pair of gym shoes, and toiletries. I make sure to utilize every inch of space in that suitcase. As I mentioned in my article "Pack Smarter, Not Harder," packing a suitcase is like packing a moving van - you have to be strategic. Since it's the night before, I prefer to shower closer to bedtime (although I'm a morning shower person, I can adjust if needed). I also pack the items that I won't need until the morning. For example, I know I'll need to brush my teeth in the morning, so I leave the toothbrush unpacked until then. Similarly, I'll wait until the morning to pack my phone charger block. However, I might consider packing my Roku stick for the hotel TV now (I need some entertainment after a long day of exploring!). I see packing a suitcase as a continuous process, much like cooking a meal - you clean as you go and it's an ongoing task until the very end.

tabby cat in black box
Photo by Valérie Ungerer / Unsplash

Then The Morning Comes

This is the final stage of my packing process. At this point, I am organizing my toothbrush, toothpaste, deodorant, and any other items I may have overlooked. While I typically pack a suitcase, I also bring a backpack as my carry-on item. In the backpack, I usually include my laptop, iPad, and any necessary accessories for these devices. Additionally, I always pack a pair of noise cancelling headphones. I keep the backpack light, only including essential items, as I prefer to avoid having it thoroughly searched during security checks. I usually dress comfortably, opting for clothes that do not require a belt and slip-on/off shoes. I make it a point to arrive at the airport early, as I like to be well-prepared and avoid feeling rushed. Packing as I go allows me to double-check that I haven't forgotten anything. It's important not to become too consumed by the process, but I do take care of general tasks such as turning off running water and lights. Even after taking numerous solo trips, I still experience nervousness and anxiety. However, I take a deep breath and embrace the moment. It's finally happening.

The Longest Day

My local airport isn't a big city airport, so there's always plenty of parking available either at the airport itself or at the nearby parking lots with shuttle services. Personally, I prefer TheParkingSpot because their prices are reasonable and they even offer a nice discount with AAA. I always make sure to reserve my spot well in advance, usually around the same time I book my flight. Once I arrive at the parking place, I park my car and hop on the shuttle to the airport. It's important to remember to tip the shuttle drivers nicely since they work in all kinds of weather and help with your luggage. At the airport, I usually head straight to the self-check-in for my bags. Sometimes, it directs me to the security check-in station nearby, while other times I need to check in with an agent. After dropping off my bag, I proceed through the main TSA line and keep in mind that these guys have a job to do, so it's best to be nice and relaxed. Pay attention to the signs around the security check-in, especially the one about no liquids. Each security site may have different requirements, like removing your belt or taking out your laptop and iPad, but just go with the flow and you'll be fine. Once I'm through security, I check my airline app for any updates and also glance at the arrivals/destinations wall to see if there are any changes to my flight. Whether everything is going smoothly or there are some changes, I usually try to find a convenience store in the airport to grab some snacks (nuts or jerky are always a good choice) and soda/water. I also look for a nearby food option, whether it's fast food or a sports bar, to pass the time before my flight. When it's time to board, it depends on the airline. If I'm flying Southwest, they have a system where you board based on your position in line (although you can pay extra to move ahead with the EarlyBird program). But if I'm flying Delta, American, or other legacy carriers, I usually have an assigned seat and a boarding group. I try to get there around the earliest boarding time, and then I proceed to board my flight.

I settle in, put the noise cancelling headphones on, and I privately non-verbally "say", LET'S DO THIS!

What about a road trip? What if I don't decide to take a flight? Find out next week!