One thing bout me, I’m goin take a trip.
Inspired by the travels of my mother and grandmother, I have lived my entire life with a deep awareness that there is much to be seen on this beautiful floating rock of an earth, only if I am brave enough to seek it.
But over the years, particularly in my first few solo adventures, I learned rather quickly that bravery is not the only thing you need to travel meaningfully, joyfully, and as peacefully as you possibly can.
Each trip is a blessing and a privilege. And behind each of my trips is a plan.
Since I started documenting in Dec 2021, I’ve completed 24 trips to date. That averages out to be about a trip per month for the last 2 years. While I didn’t do that on purpose, traveling that often has required me to develop a very specific skillset and collection of tools to do so with joy, peace, ease, and fun at the very center of every move I make.
And as I prepare for my biggest trip of the year, I thought this an appropriate time to document for you, dearest reader, how I plan a trip.
This piece is not sponsored or endorsed by any company, entity, or individual. The following is based on my experience, my circumstances, and my interests. My approach to travel may not be of interest to you and I need you to know that’s okay. The way we experience the world is extremely personal to us as individuals, so take what is helpful and leave what isn’t. Off we go!
Before we get into the steps I take to plan trips, it’s important to briefly discuss the systems I’ve set up to make any individual trip I take possible.
In short, I travel so often because I made travel a priority. It does not live in the “wants” section of my budget. It’s its own line item, with its own unique fiscal allocation that I’ve shifted pretty much the rest of my spending to accommodate.
It is not something I rely on others to do; I took my first solo trip at 18 and haven’t waited for nobody since. I plan first and invite later.
I also have worked a remote job for the last few years and just recently started a hybrid role. I have been blessed with coworkers and managers who understand what travel means to me and respect (and even encourage) the way I get gone.
Finally, the biggest key to my success is travel seasons. I’ve done a lot of trial and error over the last few years to figure out how I can travel better, but the greatest takeaway I have from my experiments is traveling in seasons that are conducive to me and the annual patterns of my life.
Those are truly the key ingredients, but there is still more that goes into it. To plan a trip, I need to have a system to organize it and some change to pay for it.
Dear reader, I present to you my Travel Plans Notion Board.
Side note: If you’re not already on Notion, you should certainly go do that. I was introduced to Notion in 2021 by a few dear friends and quite literally have not looked back. The opportunities for organization are endless in this application, I assure you. They’re not sponsoring this piece, but shoot they should be lol
What you see below is a portion of a view of my Travel Plans board.
This singular board contains every detail for every trip I have taken since December 2021 and extends to March 2029. This is my source of truth, holding nearly every receipt, flight number, payment history, and dinner reservation within its user-friendly hands. It is a space for transparency, collaboration, and negotiation. It is the way I get it out of my TikTok bookmarks and my IG DMs and into my reality.
First of all, God. *praise break*
Second of all, I’ve somehow consciously and perhaps subconsciously created a life that is especially conducive to a regular travel schedule. I currently have very minimal expenses, partially because I’m afraid of bills but largely because I want to reserve as much disposable income as I possibly can for my adventures. I don’t drive a 2025 big-body Benz, I don’t live in a high-rise in Midtown, I don’t have a dog (yet, y’all pray for me lol) and I do not have any European designer bags in my closet.
I shop at Kroger and Sam’s Club, live at home with my mama, and go to the High Museum for fun. I, in the crucial habit-building period of my young adulthood, essentially created a fiscally intentional lifestyle that was specifically designed to ensure that I always had enough resources (time and money) to sponsor the upcoming travel season a year in advance.
I plan to move out soon, though, and I’ve been gradually understanding just how large of an expense that will turn out to be. But I’m working very diligently now to ensure my financial security prior to making that move so that regardless of the job market, not only will my expenses be satisfied for at least 6-9 months, but so too will my travel season remain intact for at least a year.
Third of all, travel credit cards. I’ll defer to my friend, Jared Seller Bryson, and his SellerSaves approach of using points to see the world. The thesis of the approach is to always “use more of their [the banks] money, and less of yours.”
His approach and advice have allowed me to completely stop paying cash for flights, saving literally thousands of dollars just in the last year alone. Reducing the cost of flights has drastically reduced my per trip expenses, leaving me with more change in my pocket than before.
The exact step-by-step process I use is highly informed by my background, experience, and interest. It’s also quite fluid based on the unique circumstances of the trip itself. With that being said, here is what I would call a true how-to.
When I’m planning a trip from scratch, the first two questions I ask myself are when and where. I can start with either one, but they must be answered together.
When can I go and is that a good time to go to that destination?
Where is a good place to go during this time I’d like to go?
You can start with either question, but these are settled before I go any further.
🛠️ Tooltip: I often consult Google Flights’ Explore feature to navigate these questions. Just plug in some dates, play around with the globe, and see where you land. If you’re using points, cross-reference that with pointsyeah.com and seats.aero to find the best deal for you.
Once I’ve identified a destination, the dates, and the airline I’ll be transferring my points to, I book all these things! But I do them in phases.
The first thing I book is the flight. I transfer them points, book my flights in one-ways, and plug my flight details into my Notion board.
Then, I start hunting around for an Airbnb. I am frankly quite slow with this part depending on how I feel, how high the demand is for the time I want to go, and how far away the trip actually is.
And somewhere in between those two, I book or reserve my big ticket itinerary items. That’s the concert ticket or the dinner reservation or anything else that needs to be booked ahead of time. I don’t plan out the entire itinerary this early, but the key activities are often booked and on paper well in advance.
Ah, the fun (but optional) part.
It’s optional because, truth be told, you don’t need an itinerary. Or at least as strict of an itinerary as you might think.
Now, I love a plan and a schedule as much as the next planner girly, but in my experience, I’ve grown to understand that the key to a well-planned trip is to slow down. And slowing down may, to the untrained eye, appear to be abandoning a plan altogether.
Slowing down in trip planning means identifying an anchor and side missions, instead of just marring your calendar with every single activity you see on the internet.
For a longer trip, try finding a couple of anchors throughout the week (things you really want to do or things that require reservations) and a few more side missions to fill out the day.
I’m drawing inspiration from my 2022 Barcelona birthday trip to plan Osaka 2024. As I recall my time in Spain, I’m reminded just how much joy can come out of intentionally moving slowly, especially in cities you’ve never visited. We kept it extremely simple, no more than two scheduled activities per day, and even those activities were far apart in time. The day before my birthday, we scheduled horseback riding and made that the singular activity. Later that night, we ended up getting drinks and learning Bachata in a random alley bar with friends we had made that morning, but we were able to do that only because we left space for it.
Free space on an itinerary allows you to walk a little slower, spend a little extra time at the cafe, take a few more pictures, sleep in a little longer, or stay out a little later. When you leave room in your itinerary for spontaneous adventure, it will surely come. But if you try to plan out every hour of every day, you’ll find yourself with less time than you imagined.
If you’ve read this far, you must be seriously considering taking a trip. And I love that for you. I pray this has been an encouraging resource for you that has empowered you to press “reserve” and “book” to wherever your heart desires.
If you are new to traveling and a little nervous, hear me when I say that it’s okay to be scared. Doing new things is scary, I know, but you and I are far braver than we think. If this is what you want, I encourage you to think deeply about what it will take for you to get it. Yes, it can get a little complex and, of course, there are an infinite amount of travel horror stories on the internet, but when you take your time, focus on doing your best, and move with both curiosity and confidence, you’ll find yourself traversing the world in a way that just might change your life.
See you at the gate, bestie! Safe travels!
Thalia's just happy to be here, to be honest. God is good!!!
