How to book flights as a Digital Nomad

Things to consider before buying that ticket and taking the ride.

6/4/20233 min read

I want to buy a fucking flight to Thailand and it’s proving harder than I originally anticipated. Well, mostly because I don't want to fuck up. After years of painful boarding times, challenging logistics to the airport and a generally uncomfortable experience navigating new airports - timing can be everything. I’m based in Portland Oregon and while the time difference shouldnt be that challenging to navigate, I’m still paralyzed with fear in pulling the trigger on committing a couple thousand dollars to an airline I’m not overly familiar with before ensuring that I’m not royally fucking myself with the timing of everything.

Just this year, I had the entire process of planning executed to a tee and then it turns out that local flights through Tunisia have a very specific gate tucked deep in the basement with somewhat unclear departure times. This why here are some factors that you’d generally want to think about when timing flights:

Understand Time Zones and Destinations:

I’m a big time (pun intended) user of - this is an easy way to map out where you’re at, where you’re going and everywhere in between in consideration of time zones.

Research Peak and Off-Peak Seasons:

Peak seasons are real, generally a simple google search will guide you in right direction but there are cultural events to consider as well that might not be so obstinate when you look up “peak season for blah blah place” - be sure to cover google topics like “holiday, festivals, and political conflicts” when researching the timing of your travel.

Consider Departure and Arrival Times:

Everyone is different - maybe you love waking up at 5am and being the first person in the cafe line or a low flow at security. There are definitely pros to showing up early, as in you have a lot of options if something fucked up happens to your flight specifically the cons are…you have to wake up early and being half awake in that fluorescent lighting can be a real son of a bitch. A mid day flight is almost always going to be the most convenient and therefore, the most expensive. A later day flight is pretty clutch because you have all day to consider the how and when to get to the airport, you can have some nice dinner/cocktails if you roll in to the airport early enough but then you have to consider…the later you leave the later you arrive and late arrival times can present challenges around checking in to your accommodations. SO MANY FACTORS TO CONSIDER.

Analyze Flight Durations and Layovers:

Nonstop is king. Maybe one or two layovers isn’t totally hateful but it’s helpful to have some level of familiarity with the airports you’ll be stopping in. If you have to do a long layover, it’s helpful to do some reconnaissance around the airport hotels or lodging options closeby. The last thing you want is to arrive into a 7 hour layover with over 2 hours of commute to and from the airport to consider (Hi, Istanbul). You get to sleep 5 hours now, maybe if check in is easy. Maybe if cab is available

Utilize Fare Comparison Tools:

I’m a hardcore airline loyalty person because I dont have the time or the dopamine to dedicate to gamifying the airline industry at large. That being said….Google flights is where I start all my searches. This guides my timing decisions for dates as well as serves as an easy access to all the airlines that fall under my loyalty program by simply selecting “star alliance” under the dop down for airlines. 3rd party sucks. I know this from years of working in the hospitality industry but they can provide some good deals so you know, buyer beware.


Don’t think too optimistically when booking your flight times and logistics around them. Too many times I’ve said “sure it’ll be easy to find a cab at 5am in Antigua, 1.5 hours away from the airport and get through check in and security all within an appropriate boarding time with zero stress”. It’s never been worth the $40 savings my guy, literally never. Be brutally honest with your timelines and needs when scheduling flights and you can thank me later when you’re sipping a $17 cocktail while you comfortably wait to board a flight in 30 minutes.