How I Choose And Book My Flights: A Peek Inside A Full-Time Nomad’s Travel Planner

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I seem to have lost my edge in retirement 🙂 . I used to be a badass that took 6am and redeye flights to save money, while disregarding my sleep and chugging coffee until my heart felt like a hummingbird was trying to leap out of my chest…and I thought that was a good thing 😉 .

I was a bit brainwashed by our go, go, go culture and now I value my comfort, sleep and happiness way more than saving a few dollars. So I thought it might be fun and helpful to go through how I book flights in retirement – what criteria I look for and any tricks I’ve learned along the way. This will be similar to the post below I did about Airbnbs, but for flights!

I guess I’m starting a whole series now 😉 . If there’s any other aspect of my nomadic life that you’d like me to expand on in this way, feel free to let me know in the comments.

Since becoming a full-time nomad almost 3 years ago, I move locations about every month. Surprisingly since I’m staying mostly in the US and similar time zones to accommodate my partner’s job, that hasn’t meant I fly every month. I used to think that the US had nothing on Europe’s ease of pedestrian and train travel, and while that’s still mostly true 😉 , I have been surprised by the ease of using Amtrak around the northeast and even up the west coast, which I wrote about below.

At other times we’ve rented a car to road trip through multiple states and see beautiful things along our journey. Basically there have been less flights in my life than I expected or while I was working. We fly about every 3 months and when I do, this is my criteria for domestic flights:

  • Direct flights (and if no direct flights are available, a short layover)
  • No early flights (before 12pm 😉 )
  • No redeyes
  • Plane with in seat televisions
  • Weekdays for less busy airports and usually cheaper flights

I know, I’m bougie 🙂 . I also feel fortunate that I can choose flights based around my preferences instead of what’s available or cheapest. I prefer direct flights because they take way less time and also have less margin for error because of delays.

I don’t enjoy early flights because if my flight leaves at 9am for example, I would arrive at the airport at 7am, which means leaving home at 6am and getting up at 5:30am at the latest. Getting up that early inevitably means that I’ll sleep like shit because I’ll be worried about missing my alarm. So I just don’t pick flights that early.

Similarly, redeyes are usually overnight flights and I have rarely successfully fallen asleep on a plane in an economy seat (international business class like the below is another story entirely 😉 ). If I try, I just end up watching movies through the whole flight and arrive the next morning at my destination exhausted and craving bed instead of my next adventure. So I don’t take those flights either.

Delta, the airline from my hometown of Atlanta, almost always has personal televisions on their planes and I prioritize that for longer flights because I don’t love watching shows on my phone, and my computer doesn’t seem to play nice with plane wifi.

I also try to target weekday flights if it works with my partner’s work schedule, because airports are less busy (people…*shudder*) and the flights are usually cheaper. Now you may be wondering: how do I make sure I get all of these things when searching for flights? I’ll tell you 🙂 .

Google Flights

I use Incognito Mode to hopefully avoid airline website cookies following me and increasing prices for flights I look at often, and then I head to Google Flights (#paranoid). Google Flights lets me filter for all of the above criteria as well as if carry-on luggage is included in the ticket price because for some reason, some airlines (that I try not to fly) have started charging for carry ons and I’m not about that noise. I can also see amenities on each flight, such as in seat TVs right on the same search engine. After I decide to buy a flight, I head to the airlines website directly and buy it.

Flight Aware

Then I go about my life until the day of my flight arrives. At that time, I visit Flight Aware and search for my flight number. This site has a lot of helpful information, such as the “Where’s My Plane Now?” feature. It tells me where the plane I’m flying is at that moment, if it’s delayed, and what gate it’s going to.

This gives me a heads up if the plane departed its last destination late, or if there’s bad weather along the way, or if it’s heading to another terminal so I might be getting a gate change announcement soon.

TripCase

To actually receive that announcement, I happen to trust TripCase more than overhead announcements or even the app of the airline I’m flying. I’ve used TripCase for almost a decade to keep track of my many travel plans and mentioned all the ways I like to use them for that function in the post below.

However, the one way I’ve found that they’re unlike other travel aggregator apps, is that at least anecdotally for me, they always tell me about flight cancellations and gate changes before anyone else. I don’t know how they get that information and disseminate it first (time machine?), but I’m very impressed and grateful.

Conclusion

And that’s how I choose and book flights in my nomadic life! Or put another way, here’s how I make sure my travel is in the perfect “Goldilocks zone” 😉 . Safe travels!

How do you prefer to book flights?

18 thoughts on “How I Choose And Book My Flights: A Peek Inside A Full-Time Nomad’s Travel Planner

  1. *grabs her cane* In my day, when I was a wee girl, I remember when the airlines had checked luggage and carry-on included in the ticket price, everyone got a snack and drink, and you could carry full bottles of water through security *shakes cane* it was better in the old days! Even though major international flights only happened like once a week (depending on location and routes) and tickets were more expensive, it was better!

    Flights are much cheaper now, there are more of them, and the airlines are trying to make money where they can, especially in wake of the pandemic. I recognise all that, but my god it’s so frustrating when I can remember how special and nice flying used to be. That being said, EasyJet over here has been charging for a “large” cabin bag for years now and other airlines have followed suit. I’ve responded by packing lighter and lighter *shrug* turns out that works nicely and I don’t need most of the crap I think I do for short trips.

    I use Skyscanner, I also go incognito mode, and I manually clean out cookies once or twice a year (and before any major flight bookings). I’m with you on direct flights wherever possible and avoiding early/redeye flights (I still find myself doing them occasionally, but I try not to). Just not worth it anymore.

    1. All fair points and good to know about EasyJet! I didn’t know those kinds of carriers were charging for certain kinds of carry ons, but all that info is super helpful in advance of my next Eurotrip 🙂 . I’ll check out Skyscanner – I’ve been wary of aggregate sites besides Google Flights for some reasons, but should expand my scope. Thank you!

      1. I use Skyscanner to find flights, then I go to the airline site and redo the search there to book the flights. I never use Skyscanner to connect with the airlines or make a booking. Just use it as a search tool.

        Yeah, EasyJet will nickel and dime you – they charge for large cabin bags as well as checked, and for seat reservations. You do get priority boarding if you purchase certain seats. You don’t have to buy seat reservations if you don’t care where you sit, they’ll allocate you a seat at check in anyway. They’re so damn cheap and fly everywhere, it’s hard to get away from using them XD

        Other airlines have rates like “Economy Light” “Economy” and “Premium Economy”, where the light version is just a cabin bag. I know I’ve seen BA and Lufthansa do that. The big carriers are generally more reliable in terms of scheduling and a bit more generous with baggage allowances.

        Stay away from Ryanair if you can. Budget travel hell.

    2. heh, I also remember the old days when you had to call (on a telephone) the airline directly to book a flight or use a travel agent. I struggle with phone calls and aural processing in general but luckily I only had to do it for a few years before the internet caught up with technology promised us in ‘The Net’ 🙂

    3. I kinda miss the tickets printed in a booklet with each copy torn off and handed over per leg. Just something about the red carbon paper and the feeling of each ticket. Wouldn’t trade it for electronic tickets since can’t beat the convenience but I still miss those days.

  2. I’m with ya 100% re: no red-eyes or morning flights! Problem is, there are often no other practical options for the route I need to take. 🙁 Unless I add 20 hours and three layovers. Sigh.

    1. Fair. If it’s all there is I’ll take it, but I have my ideal preferences 😉 . I hope a better route opens to you soon!

    1. Last I checked TripCase is all free and TripIt charges for several important things TripCase does for free 🙂 . Do you prefer TripIt? If so, I’m curious why! I’m always looking to improve my travel game 🙂 .

      1. Yes I prefer TripIt. I know they work pretty similar (forward related mails to an adress and they process it) and so far I used both in their free version along each other for a few trips and honestly I just like the TripIt user experience a little better. I feel like TripIt recognizes a little bit more attributes from processing the forwarded mails and displays them a little neater and cleaner in the iOS app. Plus the webapp is nice, too.

  3. I am on a business trip all week this week, but all I can think about is FIRE. So I was mindless browsing on Google and came across your blog this morning. Right after I got back from work, I saw that you have a new post! It’s very encouraging to see your success stories, and hopefully sometime next year, I will have the courage to pull the trigger! Thank you for sharing your stories!

    1. That’s super cool! I hope you can pull the trigger too 🙂 . Thank you and I hope you have a great rest of your week!

  4. I’m an early riser so I like early morning flights. I know; I’m crazy. 🙂 I use Google Flights to track prices and one bag whenever possible. And I give myself permission to upgrade my seat whenever I feel like a flight is going to be unusually stressful. For example, I flew to Boston on vacation last year during the time when the airports were unusually hectic and baggage was being lost/misdirected a lot. I was in premium economy but, after watching the news reports, I spent the extra $60 and upgraded to first class. I still had to deal with crowds at the airport but at least once I was on the plane that extra bit of personal space helped me destress.

    I remember when flight attendants handed out wings and coloring books to kids on flights. If the airlines handed out coloring books to all passengers (kids and grownups) on their flights I bet everyone would be a lot less stressed out.

    1. Naw – I’m glad someone is enjoying those early flights 🙂 ! And that’s awesome that you choose to upgrade in situations that will lower your stress. I love that and do same. And oooh I vaguely remember coloring books on flights…or maybe I’m thinking of restaurants…Either way I am SO down to color on flights. It does help me relax.

  5. Early bird here, I see no issues to flight in the morning. I would do any efforts for a holiday 🙂
    Still on accumulation phase, still I look at every 50€ spend, can’t wait to have same ‘issues’ as you. Google Flights is my friend, then I go on the company site.
    Another parameter for me is where is the airport and if I can arrive easily and cheap there. Where I live, there are a few airports under 2 hours far away but some are difficult to access with public transport and this might cost more than worth a cheaper flight.

      1. Thanks for the tip! I never noticed that. Does that indicator mean that they have a screen on the seat in front of you, or does that include flights where you will need to bring your own device to watch it on?

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