Best Results Organizing

Summertime is a high travel season. If you’re ceaselessly online, when you hear “travel,” you’re probably stuck on the non-stop loop of “Nothing Beats a Jet 2 Holiday.” (If you just got the jingle out of your head, I’m sorry.)

Otherwise, you’re either traveling, yourself, or comparing travel horror stories. But as you’ll see, a little organization can make these experiences a little easier to stand.

ORGANIZED TRAVEL IN A DISORGANIZED ERA

Trapped on the Tarmac

A few weeks ago, I did my own little version of Planes (No Trains) and Automobiles. The plan was to fly to Buffalo (by way of Atlanta) for my 40th high school reunion, and after a week with Paper Mommy, rent a car to drive to a friend’s combination vow renewal/housewarming/birthday party in Massachusetts, followed by a short drive to an airport in Connecticut and a flight home (again, by way of Atlanta).

Any trip with that many moving parts leaves a traveler open to a few kerfuffles. There was a one-hour delay on the New York State Thruway near the village of Canajoharie when one 18-wheeler sheared off the back of another 18 wheeler that was carrying giant bags of cat food, littering the highway with both bags and actual loose cat food.

On the return trip from Connecticut to Atlanta, the gate agent seemed particularly surly as she informed us that the airline had oversold the flight, and nobody would be boarding unless three people agreed to give up their seats and fly the next afternoon or evening, and agree to be without their luggage until they did fly! (This came after I circled the airport twice, passing the “Rental Car Returns” sign each time, because my GPS insisted that I should continue further along and return my car to an empty field.)

However, the anecdote that prompted this post was my connecting flight from Atlanta to Buffalo. We boarded on time, but passengers immediately noted how warm the plane was. After everyone had fastened their seat belts, and had their tray tables locked and seat backs in an upright position, we heard the various bing-bongs, but went nowhere. Eventually, a weary voice intoned, “This is your captain speaking…” and we learned that there was a “minor mechanical problem” and we would be delayed fifteen to twenty minutes. 

 
(This wasn’t my flight. But in a way, don’t we all feel like this was our flight?)

The temperature continued to rise. Passengers were polite and resigned, except that after about half an hour, an announcement was made that there would be another delay of about twenty to twenty-five minutes. This continued for about an hour and a half, when we were assured the problem had been fixed and that pending ten minutes of “paperwork,” our flight would take off. But it didn’t.

We were then told that there was a lightning strike on the field and that all ground crew were ordered inside, so we needed to wait until the weather cleared. At this point, our phones’ weather apps told us it was in the 90s outside the plane; you can imagine how high above 100° it reached inside. 

After two hours, a small rumble of rebellion fomented. We were hot, thirsty, late, and cranky. 

Over the course of time, passengers started air-dropping and sharing Department of Transportation regulations (of which, more later) about traveler rights regarding delays. After more than 2-1/2 hours boiling inside this elongated metal hot box, we were told that we would de-plane and it would be decided whether we would re-board or be assigned a new plane. (This made us wonder whether the weather issue had been valid at all; had our plane truly been fixed as reported, why would we have needed a new one?)

Long-story-short, we deplaned, had our re-boarding scheduled and canceled multiple times in a short period, and then we were assigned a new plane — which would take off a little more than four hours after our originally scheduled flight. 

Welcome to airline travel in 2025.

The Chaos of Air Travel

Of course, my experience is one of many, and a relatively insignificant one. A few days after this, Alaska Airlines grounded its entire complement of planes — 200 flights in all — over a Sunday night and Monday computer glitch.

Because travel has become more chaotic (and more controlled by digital systems), it’s increasingly necessary for consumers to organize their resources to prepare and respond to this chaos. In this post, I will highlight some of the essential information you need and actions you can take to guard against travel frustrations.

Pre-Trip Prep: The New Administrative Burden of Travel

Do you recall the days where you’d call a travel agent, explain where you wanted to go and when, and be presented with a nifty little itinerary and all the information you might need until you arrived at the airport (with your non-wheeled suitcase and traveler’s checks in hand)?

Online check-in and e-tickets began in the 1990s, and though it’s shocking to think how recently it actually was, we didn’t have mobile check-in until 2007, and it wasn’t widely adopted for several years after that. (For those interested, CNN’s Final Call for Paper Boarding Passes: A Visual History of the Beloved Memento offers an interesting look back.) 

Book Your Travel Arrangements — With Padding

This is not a travel blog, but one focused on organizing and productivity. If you want good advice on booking travel, I direct you to:

• The Points Guy (especially for using credit card, airline, and hotel reward points for booking)
• The Blonde Abroad (focused on solo traveling for women)
• Nomadic Matt (great for coverage of wide-ranging travel tips and news)
• Budget Traveller (particularly for adventurous but cost-cutting travelers)

Travel is messier than ever. It’s not uncommon to hear tales of canceled flights and travelers sleeping in airports, even when weather is not a factor. My advice is to always book your travel with at least one day of padding in case things go awry. 

I discourage you from ever scheduling a flight the same day that you need to be anywhere or do anything; that will guarantee more stress than is necessary. 

Log all of your travel information

Those 1970s-era travel agents? They provided tickets, itineraries, and nicely organized lists with every date, time, and confirmation number. You are your own travel agent now.

Whether you create a digital, analog, or hybrid record of all of this information is up to you. However, whatever you do to log your essential travel information, provide a copy to loved one or trusted assistant. If technology fails and/or you and your documents are divided, having someone able to see your travel arrangements (and possibly help you alter them from afar) can be the real golden ticket.

Confirm everything a week in advance

During our junior year in college, my boyfriend was seeking a placement for a summer and semester in engineering co-op (basically, a fancy science-y internship). He painstakingly wrote down the details arranged by the company’s office, and arrived on-time at the airport — a day late.

It’s easy to mis-remember details, or to misread what you’ve logged or see in an app. Check your dates and times, even if you’re 100% absolutely, positively sure. 

Check in when prompted

Nowadays, check-in has become a part-time job for travelers. I traveled extensively up through 2019, but must admit that I hadn’t traveled (by air or stayed in a hotel) since the start of the pandemic, and was by turns surprised, annoyed, and flummoxed by all the different types of checking in to be done. You will be asked to check in a day prior for:

• Flights — You’ll generally get a prompt to check in 24 hours in advance of the first flight in whatever sequence of flights you have. If you haven’t booked via an airline co-branded credit card, you will likely have to pay a fee for your baggage; do it at this time and it will be one fewer thing to worry about when you get to the airport.

• Hotels — I’ll be honest, I wasn’t expecting to have to do this and was surprised when my hotel sent me a text and email to prompt my check-in. 

This is where another travel kerfuffle took place. I clicked on the link in the text, which took me to the hotel website, but the page was insistent that my booking did not exist and suggested I call. (I was just delighted that I wasn’t routed to an AI bot.) The phone system immediately recognized my cell phone number and the automated attendant asked if I was calling about my hotel reservation for the next day — at least the robot lady knew that I had a reservation, even if the web site did not.

It took twenty minutes with a lovely gentleman to accomplish the digital check-in; eventually, I had to download the app, log in (twice) and (I think) spin around three times and bow toward the ocean, but eventually it worked.

For this reason, having your confirmation number and reservation information logged and handy will help ease whatever pain the process requires of you.

• Rental cars — Yup, I wasn’t expecting this, either. Admittedly, every time I’ve had to rent a car in the past 5 years it has been (sigh) because someone has hit (or stolen) my car, so the reservations have been handled by insurance companies, and the car rental companies have called me to confirm, so I have never had to check in.

• Tours, transfers, etc. — Basically, any arrangements you have related to travel, whether it’s a car service, a tour, a transfer (like from plane to bus for a group booking), etc., will likely have a booking. Anticipate your check-ins so that your busy day-before-travel workload is not interrupted unnecessarily.

What happens if you don’t check in? 

Wondering what happens if you just don’t bother to do a digital check-in as prompted? Consequences vary.

On a flight, your seat may be given to someone on the stand-by list, particularly if you arrive late to the airport. You might miss important information or changes to your reservation, causing you to be late or miss the trip altogether. Your hotel room could be given away, or your priority level could be reduced.

ORGANIZING YOUR TRAVEL INFORMATION

The New Tech Landscape of Travel: Apps You Can’t Escape

I’m not going to tell you that you have to have all of these apps, but I can tell you from recent experience that downloading travel apps and having the passwords accessible in a digital password manager will save you headaches on a rough travel day. So, at least consider downloading the following apps and saving them all in one travel folder, moved to your phone’s first page on travel days:

• Airline apps – Although you can check in to a flight in your computer, phone, or tablet browser, airline apps are pretty much de rigueur for managing check-ins, downloading boarding passes (or sharing them to your digital wallet), keeping abreast of gate changes, arranging re-bookings, etc. The app makes everything smoother.

Across the four flights on my trip, but particularly that hot-box delayed-flight experience, the app alerted me to each change (and even to the location of my suitcase each time it was relocated) long before the pilot or gate agent informed us of anything. Because the new plane was larger and had a different layout, my boarding pass and seat assignment changed, seamlessly. I just had to consult the app.

• Hotel apps – You may be wondering why you need an app to basically rent a tiny piece of real estate for a day. (You may also be wondering why you book a hotel “by the day” but can only check in at 3 p.m. and must check out at 11 a.m., getting only 20 hours of any “day.” Sorry, no clue.)

Hotel apps now not only have digital check-in and check-out, but keyless entry and the ability to control the TV, thermostat, and lights, order room service, request amenities (like more towels or toilet paper) or to chat with front desk. If you are an introvert, hotel apps must be a saving grace!

Note, however, that like most of modern travel, boo-boos occur. My Hampton by Hilton digital key on the app should have allowed me to hold my phone against a plastic square above my doorknob to unlock the door. However, after several attempts on my own and multiple re-settings by the front desk dude, my digital key never worked to enter my room. (Strangely, it operated as expected if I wanted to use the fitness center, pool, business center, and laundry room. Apparently, the app felt strongly that I should be a fit, productive, and clean traveler; it just didn’t want me to sleep or be well-dressed.)

I was given a plastic key card, like the kind we’ve been using at hotels for thirty years; however, instead of inserting it anywhere, it required waving it in front of the aforementioned doorknob plastic square thingy at just the right angle or speed. 

(For germaphobes like me, being able to control the TV from my phone instead of having to touch the hotel’s remote was a nice feature.)

• Car rental apps — Whether you opt for the old standbys like Hertz or Enterprise, or have embraced peer-to-peer car rentals like Turo (basically an AirB&B model for car rentals) – an app may be necessary for everything from rental check-ins and returns to unlocking the vehicle.
• Ride share apps — If you spend more time in Ubers or Lyfts than in your own car, you’ve probably got the apps already, but if you only use them to get to/from airports once every few years, you might want to re-install and make sure your saved credit card info is right.
• Master itinerary managers — If you prefer a formal platform to DIY-ing your trip, an app like TripIt allows you to gather all your hard-won trip-planning successes in one place. You forward all of your travel confirmations to the app, and it automagically arranges everything into a comprehensive itinerary. TripIt also includes seat trackers (in case a better place for your tush becomes available, fare trackers, point trackers, and document storage. Wanderlog is similar, but includes functions for creating checklists, tracking and splitting expenses, collaborating with fellow travelers, and adding travel guides. 
• Note-taking and cloud apps — You don’t have to use fancy apps to track your itineraries if you prefer DIY. Just print your travel itinerary info to PDF and save in a trip-specific note in Evernote, Notion, AppleNotes, or OneNote, or upload your confirmation documents to iCloud or GoogleDrive. 
• Your photo and camera app — These other apps are convenient, but if you really want a failsafe digital backup, screen-shot or make a PDF of mission-critical travel details, like confirmation numbers, boarding passes, airport maps and hotel/resort directions, and important contact info that’s too lengthy to type into your contacts app.
• Flight tracking sites/apps — Some people are comfortable trusting the airlines to keep them informed. The rest of us obsess and need to know if our connecting flight is leaving late or if there’s weather that’s going to make our plans go kablooie or if our travel companions coming from other locations meet us on time! Two great site app options for knowing about flight and airport disruptions are FlightAware and FlightRadar24.

Organize in Case Your Tech Fails

Apps and the internet are modern and cool and essential for many things. Except, and I’ll hold your hand when I say this, tech can suck. For example:

• Some apps only work when you’re online. This is bad news if you’re in a cell tower dead zone or, as happened on my hot-hot-hot delayed flight, the promised Wi-Fi melted down.
• You phone may poop out, because the more travel kerfuffles you experience, the more time you’ll be spending on the phone.
  • Yes, you should probably travel with a hand-held charger, but if you’ve had to re-charge your digital devices many times, your charger may be weary, too.
  • Yes, there are chargers on planes, but if your charging cable is the modern USB-C format and you’re not traveling with an adapter, you may be out of luck, as the weird little charging ports down below the seats and the ones (on larger planes) in the seat-back “entertainment system” are all USB-A.
• Digital keys often fail — that front desk clerk is still your best chance at getting into your room. (When you get to the hotel, request key cards. You don’t want to schlep up to your room with all your luggage, only to find the digital key doesn’t work.)
• Notifications overload is real — Sometimes, it’s worse if all your technology works than if it fails. There’s too high a chance of important messages getting lost in a sea of “Rate Your Experience!” notifications pinging your phone.

So, as Old School as it sounds, and with apologies to the trees, print your master itinerary with all of the dates, times, and confirmation numbers.

I printed every confirmation email and arranged them in the order in which I would need to use them over the course of ten days. I popped them, along with a pen and one of my beloved purple legal pads, in a zippered Container Store document pouch. It kept my notes dry when I needed to dash a few places in the rain, and the cardboard backing of my legal pad kept the papers from getting wrinkled or squished. 

A printed boarding pass works when your phone is freaking out. If the airline or car rental place is having a computer meltdown, your printout will verify your booking and the rates and service levels you were promised.

And Don’t Forget the Telephone

Save yourself the headache of having to Google or look on the back of your frequent flier card — program important numbers for your airlines, hotels, rental car agencies, etc., into your phone. 

WHEN TRAVEL GOES SIDEWAYS: KNOW YOUR RIGHTS

The United States Department of Transportation has developed a variety of passenger rights, but many people misunderstand or get them wrong. Some highlights:

• There’s a maximum 3-hour domestic tarmac delay at which point airlines are required to “de-plane” you (unless the pilot feels that passenger safety would be compromised).
• Airlines must provide food, water, working lavatories, and climate control after 2 hours. During our first two hours on the tarmac, we had only working bathrooms. Just before the 2-hour mark, we were each offered a tiny puddle of lukewarm water, and it took almost half an hour to disseminate those.
• Passengers must be notified about the situation every 30 minutes.
• The airlines must provide flight refunds if the airline cancels or significantly delays your flight, but only if you decline whatever alternative they offer!

So, if they delay you by four hours but put you on a plane (or get you onto a competing airline’s flight), you aren’t due a refund; but if you had a “non-refundable ticket” and the airline’s delays ruin your trip such that you reject their offer to get you where you’re going a day late and many (airport snack) dollars short, you can be refunded for your non-refundable ticket.

Airplane Photo by Gerrie van der Walt on Unsplash

However, if you have a bad experience, I encourage you to contact your airlines rewards center; they have a chart for depositing extra miles for delays and bad experiences.

You have other rights, too. For example, airlines must refund baggage fees if your bags are lost or extensively delayed. There are also rights regarding compensation for voluntary and involuntary “bumping” due to overbooking. For further reading and resources:

Department of Transportation Dashboard for Airline Commitments

DOT Fly Rights: A Consumer Guide to Air Travel

Keep a PDF copy of these rules on your phone.

During a bad experience, log problems as they happen so you can request compensation later. As we never took off during that hot-as-h-e-double-hockey-sticks flight, my phone wasn’t yet in Airplane Mode, so I was live-texting Paper Mommy, yielding contemporaneous time-stamps for every frustrating occurrence. This made it easier to have my upgrade fee refunded and to secure rewards points.

Experts and seasoned travelers with whom I’ve spoken advise being polite but firm in quoting regulations if you believe your rights regarding tarmac delays (or, y’know, anything else) have been denied. 

If the airlines fail to satisfy your complaints, read section 13 of the DOT Fly Rights document (above) to know how file a complaint with the DOT if needed.

Finally, always have a backup plan. Know what other options you have for flights, rental agencies, or hotels are nearby. 

For more on organized travel:

• Paper Doll’s 5 Essential Lists For Planning an International Vacation
• Paper Doll on the Smead Podcast: Essential Lists For Organized Travel
• Paper Doll Organizes Your Space, Money, and Well-Being While Traveling
• Ultimate Guide to Organizing the Passport Process: In Person, By Mail, & Now: Online!

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We can’t control the skies, but we can control our systems. Organized travel isn’t about being perfect, but about considering what we will need and having appropriate plans and backups. Feel free to share your trips (and travel horror stories) in the comments.