Travel Tips from a Frequent Flyer

I fly a lot. I once flew 110 times which is more than twice a week for an entire year. I’ve flown on every conceivable type of plane, been delayed more ways than you can imagine, been canceled, been rerouted, had my luggage lost, had my property stolen, been detained by customs in three countries, been upgraded, downgraded, and everything in between.

I’ve been in planes during emergency landings with firetrucks zooming along beside us as we landed. I’ve been in aborted takeoffs, aborted landings, terrifying turbulence, near misses, and even managed to have a crazy passenger escorted off the plane in handcuffs when we landed. I’ve seen it all. Here are my tips.


All commercial baggage sucks. Travel Pro? They last me about a year which, to be fair, probably means they’d last the average traveller a lifetime. The blown wheel to the right is from my TravelPro suitcase after abusing it for about a year. I liked the bags, but they just didn’t stand up to the abuse of frequent gate-checking  and such.

Gate checking is when the agent at the gate tags your bag, which you then leave at the end of the jet-way (the thing you walk down to get to the plane), after which it is taken, thrown down a ramp, and tossed into the bottom of the plane. If you’re lucky, you can stand around in the jetway when you land with a bunch of unruly, rude, obnoxious people who don’t know how to take turns while the bags are returned to you after you land. Gate checking is awesome. It is also a necessity on small planes commonly used on commuter legs like the Embraer RJ-145.

After breaking too many bags, I finally just bought some flight crew luggage. I bought a Strong Bag, but another very well-made bag in use by pilots and flight crew is the Luggage Works bag. Both of these are made of aluminum and are VERY strong. The downside is that they’re a bit heavy and due to their strength, practically incompressible which means you can’t “stuff” them anywhere. When I’m waiting in line at the gate, I sit on my bag and read my kindle. Try that with one of those plastic shell bags.

Another downside of these bags is that they’re right at the limit of carry-on size and as a result, they don’t fit in every overhead compartment. If your bag doesn’t fit, try these tips: Turn it around (wheels out), turn it over (wheels up), or both (wheels up and out). If those tricks don’t work, try taking a pillow or piece of clothing and putting it under the visible edge of the bag. Sometimes the overhead door won’t close because the bottom of the bag is a millimeter out too far and raising it up solves that problem because the door is curved. Also, always make sure the overhead closes before you take your seat. If your bag is the one that prevents the door from opening, they will take it off the plane and gate check it.

Mark your bag somehow. I put yellow zipper pulls on mine made of para-cord. It’s very obvious which bag is mine, which is important because every damn bag on the plane is black these days.

I try to never check a bag, but sometimes I’ll do it if they’re begging people to check bags since the flight is so full. If I’ve got the time to spare, sometimes I’ll step up and help out, and every time I do, I regret it.

Baggage claim sucks, especially in airports like Newark (EWR) where the baggage claim is overrun with people begging for money, food, drinks, and who knows what else. Checking a bag will add at least a half hour to your trip, and that’s when everything works properly. And the airlines wonder why people try to bring too much stuff on the plane. Oh yeah, and the airlines also commonly charge for the privilege of checked bag hell. Frequent flyers avoid checking bags at all costs.

Planning your Flight

Where to sit: Frequent flyers generally prefer the aisle seat, though the window is always preferable to that hell-in-the-air experience known as the middle seat. No one likes the middle seat. If you can sleep on a plane, then the window can be good, though I still prefer to sleep in the aisle. The aisle seat means you can get up whenever you want without bothering anyone, though it also means that the other people in your row will need to bother you when they get up.

I generally don’t like bulkhead seats (emergency rows and the front rows in the cabin) even though I’m six+ feet tall. Though these seats generally have more legroom, they also often do not recline which makes them a deal-breaker for me. Lastly, these seats also sometimes don’t have as much storage as other seats and may have in-flight entertainment screens that are out of your reach. Lastly, and I should state that it’s rare, but sometimes a window seat has no window.

Is paying for extended leg-room worth it? In my opinion, yes – every time. Not only do you get more room for your legs, but you’re in the front of the plane just behind first or business class. Being in the front of the plane means you get the good food before they run out, it means you get off the plane before everyone else, and it means that you don’t need to sit in the back where you can watch the fuselage flex during flight, and yes, the plane does flex during flight because if it didn’t it would break.

Sitting over the wing means more stability during flight. A plane does something called “yaw” during flight which means that the nose and tail are not pointing in the direction of travel. This is normal (and desirable) in certain circumstances, but it can feel weird. The feeling is mostly noticeable in the very front (first class) and back (coach) of the plane but I don’t’ notice it at all when sitting over the wings or just in front/behind them.

One downside of sitting on the aisle, especially as a frequent flyer who gets to board first, is that as I sit there, everyone who walks by slams their bags into my shoulder. And by “bags”, I mean luggage, arms, butts, children, handbags, laptops, McDonalds bags, diaper bags, and anything else which which people don’t realize they’re smacking me.

Connections: Connecting flights suck. I will do whatever I have to do in order to avoid a connecting flight because nothing will turn a five-hour flight into a 13-hour ordeal like a connecting flight. The fact remains, though, that some times you must connect to get where you’re going. If I must take a connection, I always plan at LEAST two hours between flights. The time you book a 45-minute connection is the time your first flight will be an hour late. Count on it.

Plane Type: Given the choice, I will not take any flight that entails getting on a plane with propellers because some of the worst flying experiences I’ve had have been on these little prop-jets. I don’t know what it is about them, but they just don’t seem to handle turbulence as well as a jet of a similar size. To be fair, the planes handle the turbulence just fine. I, on the other hand, feel like I’ve been closed in an industrial clothes dryer set to “high” for an hour after flying in these infernal machines. Hyperbole? Perhaps, but the fact remains that after too many flights (50+) on these things, I refuse to step foot on them.

After too many exciting (exciting = bad) flights on United Express Dash 8 Prop Jets back when I was commuting between NJ and NC every week, I flew only on Embraer ERJ-145s like the one shown. The cool thing about these little jets is that they have 1×2 seating which means the seats on the left are both window seats and aisle seats. They’re so small that you need to gate-check your bag, but they’re still better than those damn prop-jets.

These days my flights are generally on larger planes, none of which have propellers, but I will still not fly on prop jets if I can avoid them.

When to fly: If you’d like to try and avoid delays, fly early in the day, and by early I mean before 8am. Delays cascade as the day progresses since a single plane may make eight segments in a single day. If the second segment is delayed two hours due to weather on the East coast of the US, then that plane may be delayed for the rest of the day even in other parts of the world.

At the Airport

Some airports are beautiful, and some airports are disgusting. Some airports are both depending on which terminal you’re in.

When you step off the escalator, get out of the way! If I’m behind you I have no choice but to shove you out of the way which is not me being obnoxious – it’s physics. Two people may not occupy the same space at the end of an escalator and the escalator keeps going regardless of your inability to realize this simple fact. If you stand there, the coming rush of people being deposited into the space you’re occupying will have to give, and that means you will get moved. Do us all a favor and get out of the way.

In fact, don’t stand in the middle of, well, anything. There are people who are in a hurry and know where they need to go. If you need to stop and think or talk or whatever it is you feel the need to congregate for, please do it on the SIDE of the open space – not in the middle. You are not in your living room.

Don’t blame the airlines for weather delays. Enjoy a weather delay – trust me, you’d rather be delayed on the ground than in a plane in the middle of that storm. Actually, I should clarify that as don’t always blame the airlines when your flight is canceled due to weather – they probably didn’t cancel your flight, ATC did, though to be fair, it is possible that the airlines cancled your regional flight in favor of larger planes. The airline really doesn’t want to cancel your flight because they like money.

Don’t blame airlines for changing gates – the airport does that, not the airline.

Don’t blame airlines for a crew that shows up late. It’s not the airline’s fault if a flight is delayed when air traffic control (ATC) puts an airport in a condition that prohibits planes from taking off or landing.

Don’t complain about mechanical delays. Would you rather fly in a broken plane? Your gate change might be because of a broken plane, too, so if you’d like to wait the six hours for them to repair the original plane, that might be the alternative to changing gates.

Here’s something that is the airline’s fault: overbooking flights. When this happens the gate attendant will offer people a voucher to take a later flight. The gate attendant has a LOT of power in this situation, and if you’re clever (and have a flexible travel schedule), you can turn that into not only a cash voucher, but an upgrade. Any time you can deal your way into an upgrade, do it.

Look, I know flying can be stressful, and I know that it’s common to blame the airlines, and I also know that the airlines don’t often deserve a lot of respect, but most of the things I see people screaming about have nothing to do with the airlines.

At Security

Yes, security sucks. Here are some tips to make it easier:

If you’re in the US, then get TSA Pre. It’s a great time saver, though as of 2016 they seemed to have screwed that up in many airports, too. Some airports have a service called Clear or some similar thing where you put yourself into their “trusted traveler” database, they scan your fingerprints and when you pass they take you to the head of the TSA Pre line. VERY nice. It’s a bit pricey, but very much worth it if you travel a lot through the airports that support it.

If you don’t have TSA Pre, please, PLEASE look up what is expected of you before you arrive. The rules are here. Some quick notes:

No, you may not bring the 64-ounce big-gulp Dr. Pepper you just bought during lunch through security.

Yes, if  you don’t have TSA Pre, then you will need to remove your shoes and your belt and go through the naked body scanner unless you’d like to be patted down by hand which takes longer. These are the rules. Accept them and keep moving. There are 900 people behind you who need to catch a flight just as much as you do.

Yes, you have to remove your laptop/Playstation/Xbox/CPAP machine/slot-machine/Prius from your bag.

Yes, you must empty your pockets. Empty means empty.

No, you probably don’t need to remove your watch or glasses, but many larger pieces of jewelry may set off the machines. Be prepared.

The biggest rule of all, which encompasses all of the above – try to keep moving.

At the gate

Be nice to the gate agent. Whatever your problem is, it’s not their fault. Imagine having to deal with literally thousands of annoyed travelers every day. How happy would you be? Be kind to them, and they can make your world better. It’s rare these days that a gate agent will upgrade you to first class since frequent flyers get the spare seats, but gate agents do have the power to make that happen. They can also bar you from the flight you desperately need to board. Such is the power of the gate agent, so be nice to them.

Your airline likely has an app that you can use to get up-to-the-minute status of your flight. Use it. The app generally updates before they make announcements, and I’ve been able to know about gate changes before the rest of the passengers because my app updated me.

When it comes to delays, one of the best things you can do for yourself is to get your airline’s credit card. On United, having the credit card will get you into boarding group 2 which is a very nice perk usually reserved for frequent flyers (Silver gets group 2, Gold and above gets group 1). Additionally, with the United card I get two passes to the United lounge which is a service I would never otherwise pay for. Why is this a good thing? Consider my experience in Newark (EWR) Terminal A during a storm.

The first pic shows EWR Terminal A with multiple flights delayed. Terminal A was built in the early 1970s and so far as I can tell, they haven’t so much as vacuumed the carpet since. It’s small, it cramped, and when there are delays, it’s a crowded mess with people scrambling to find the one power outlet hidden in the floor.

I was delayed in Terminal A and remembered that I had a free pass to use the United lounge. I found it (yes, there’s a United lounge in EWR Terminal A), handed them my card, and proceeded to live in the lap of luxury for two hours until my flight departed. Note that these two pics were taken in the same terminal in the same airport roughly 10 minutes apart. The lounge is replete with leather chairs, private work areas, a bar with free drinks, and concierge service that alerts you to your flight status.

Don’t have the credit card? You can pay a one-time $59 to use the lounge. I’m sure other airlines have similar offerings. During a severe delay in a crowded old airport, it can be very much worth the price of admission.

On the plane

I used to be afraid of flying to a degree. I think it’s human nature to think that the plane is falling from the sky when there’s a bump. Trust me, it’s not. Some tips for comfort:

Flight Attendants: Be nice to the flight attendants. Their job is not very easy, and they’re doing their best. They’re generally hired because they’re people that like people, and they’ll usually treat you very well if you do the same. All they need is a smile and a “thank you.” Is that so hard?

Seats: Every time you grab the seat in front of you it wakes that person up. I know the seats are too close together and you need to grab the seat in order to get up, but you don’t need to grab it every six minutes.

Feel free to recline, but please don’t slam your seat back – it will crush my laptop screen if it happens to be in a certain position on planes with in-flight entertainment screens. Recline away, but please recline slowly.

Please – if you have a window seat on a late-night flight, close the window. When the sun comes up it will wake up everyone for three aisles in either direction.

Turbulence: Watch the flight attendants if you’re scared. If they’re not scared, then you shouldn’t be, either. Turbulence feels scary because you’ve decided that it should be. If you pay close attention in your car, you’ll notice that the ride in your car is much rougher than it is on 99% of all flights. That said, turbulence can be scary when it’s severe. Guess what? In over 500 flights, I’ve been through what pilots call “severe” turbulence just once. In that case the flight attendants couldn’t even get back to their jump seats – they pulled themselves into empty passenger seats and buckled up. If the flight attendants are standing, there’s nothing to worry about. If the pilot tells the flight attendants to remain in their seats, then the ride will be bumpy, but there’s still nothing to worry about. Honestly, unless you see the oxygen masks fall or you hear the flight attendants yelling, “Brace!  Brace! Brace!”, there’s probably nothing to worry about. You’re not falling from the sky.

By the way, I’ve been on flights where it feels like I was falling from the sky. People afterwards insisted that we “dropped hundreds of feet”. We did not. How do I know? Physics.

The inside of the cabin is about seven to ten feet high. If you put a laptop on the tray table in front of you and the plane “dropped 100 feet”, the laptop would slam into the ceiling. In fact, if the plane “dropped” even ten feet the same thing would happen. If the plane does descend but doesn’t descend fast enough to make you and your items weightless, there’s nothing to worry about.

If you don’t believe me, consider the fact that they give you open cups for your drinks. The next time you’re driving somewhere, put an open cup of ice water on any flat surface in your car and see how long the water stays in the cup.

Bending Wings: Oh, and no – the wings won’t break off. They’re designed to move, and in fact, if they weren’t flexible they would break because, well, physics. Don’t take my word for it, let Boeing show you.

Certainly there have been news reports of people being injured when the plane encountered severe turbulence. A quick note about those events are in order: first, they’re on the news because they are rare events. Second, in probably every case of a passenger getting hurt during turbulence the passenger was not buckled in, which brings me to my next point.

Seatbelts: Put on your damn seatbelt. If the seatbelt light is on, sit the hell down and just wait.

When the plane lands, sit the hell down until the seatbelt light goes off. The plane is forbidden from taxiing unless everyone is seated (otherwise the flight attendants would be up and working). Wait for the bing when the light goes out after the engines wind down, and then get up.

Due to the nature of modern airliners, the people with aisle seats will be the only ones getting up in a crowded plane. This is one of the many reasons that frequent flyers prefer aisle seats.

Noise: I travel with earplugs in my pocket. I wear them in the hotel when I’m sleeping ever since I had a road crew working outside my room at midnight in Ireland. I also wear them on the plane. The constant noise will ruin your hearing more than sudden loud noises will. I also wear them when waiting at the gate because noise adds stress. I like the blue Hearos because they’re comfortable, cut out a lot of sound, but still leave enough that I can hear announcements and listen to flight attendants and gate agents when need be.

A lot of people fly with noise canceling headphones. I’ve tried them all, and when I say all, I mean I’ve owned probably 10 different brands, all promising to deliver blissful silence on a plane full of engine noise, crying babies, obnoxious snoring passengers, and the obnoxious laugh of that woman sitting right behind you. Guess what, they all suck. Yeah, I know, you’ve got a pair and they’re awesome, only they’re not. There’s a reason Bose has a terrible reputation in high-end audio circles.

Forget the Bose headphones – they suck. To be fair, they do cancel out some of the sound from the engines, and thta’s where they shine, but they do nothing to cut out babies, snoring, talking or anything else that isn’t basically a droning noise. They’re also too damn big for an environment where carrying less stuff is good, not to mention the fact that they take batteries which is one more damn thing you need to bring.

If you’re going to spend the money, get yourself a set of Etymotic ER4Ps. They’re infinitely better for listening and just block out the sound instead of trying to magic it away with science (and power). They’re also small enough that I carry them with me everywhere.  Highly recommended. If you don’t like the flat response of the Etys, there are many other in-ear monitors like this, and they all block sound the old-fashioned way, which is to actually block the sound.

Your Head: Forget about the neck pillows – they don’t work. If you’re on a redeye, they’ll probably give you a small pillow. Sit up straight in the seat and put that pillow in the small of your back. It will help you to sit properly and your neck will hurt less when you sleep.

Modern airline seats have headrests with wings on them. These wings fold out to the front which forms a cradle for your head. Pull  these wings forward until you have a perfect headrest. I must have flown 100 times before I noticed these little marvels, but to be fair if you’re short or very tall your head may not reach them, which sucks. I’m six feet tall and they work great for me after I slide them up, and yes – they slide up and down, too!

Bring a soft jacket when you fly, even if it’s hot where you are when you depart. If it’s cool on the plane, it will keep you warm. If it’s warm, you can mash it up and use it as a pillow if you’re in a window seat. If you don’t need it, you can stuff it into your bag or use it to make your bag fit in the overhead.

I see some people lean over and rest their head on the tray table from the seat-back in front of them. Whatever works for you to sleep on the plane is worth it, so long as you’re not annoying the people around you.

Entertainment: Load up your phone and/or laptop with music, TV shows, and movies. That way, if the plane charges for entertainment you can watch your own stuff without it costing anything.

Brink a book. Better yet, bring an e-reader. My Kindle takes up very little space, weighs less than many paperbacks, contains hundreds of books, and perhaps most importantly, includes a backlight.

If you must use your laptop, tablet, or phone while the cabin lights are dimmed, please, PLEASE, turn the brightness down. I’ve sat next to people who lit up a third of the plane with the electronics because they insisted on burning their retinas with a device set on “suntan”. Turn the brightness down. It will not only let you sleep better, but it will be kinder to your fellow passengers who are trying to sleep.

By the way, the picture of my Kindle next to a cocktail was from one of my trips where I got upgraded to first class because of my status. I love first class, but I would never pay for it because it’s usually priced ridiculously high. The rare exception is that sometimes the airlines will offer me a first-class upgrade for something like $100. If you ever see that sort of offer when booking your flight, and you can afford it, jump on it because that’s a great deal.

Food: Bringing your own food on board is perfectly fine, but please don’t bring something that fills the plane with aromas (pizza) or odors (seafood).

Customs and Immigration

If you’re in the US, sign up for Global Entry. It is the greatest thing ever, and yes it’s even better than TSA Pre. Yes, you’ll need to be fingerprinted and go for an interview with a humorless gun-toting government agent, and yes, you’ll be on yet another list, but that list gets you through customs and immigration faster than you can imagine. It is totally worth it. I signed up after I was detained due to someone with my name enjoying a crime spree in another state. I asked them if Global Entry would have prevented the excitement and they said, “Absolutely.”  Sold.


I am a lifetime Marriott Platinum Rewards member because I have accrued over two million points and have stayed over 750 nights in a Marriott, most of which was back when I was an independent consultant. Is Marriott the best? I have no idea, but they are almost ubiquitous and have many levels of brands which makes it easy to find one. The Marriotts that have a concierge lounges are fantastic though because I can stay there and not worry about breakfast or dinner. You need to have status to use them unless you pay for the privilege, though.

I prefer to stay on a high floor because then I don’t hear the noise from the street, the pool, the parking lot, or the lobby.

Is it worth paying a little bit more to stay in a better hotel? In my opinion, yes, every time. Cheap hotels suck. I need sleep (so do you), and a nicer hotel makes that more likely.

Rental Cars

All rental car companies suck. I use Avis because I have for years and know what to expect. Don’t be afraid to tell them if you don’t like your car. They’ll give you a different one. Don’t be afraid to ask for bluetooth so you can use your phone in the car. Look carefully at the prices when you book. A full-size car may only be $10 more than a compact. Remember to fill it up with gas before you return it or you will be charged a ridiculous price for fuel. Some companies will let you pre-pay for fuel which may be a good option, but you’ll need to know the current rate for fuel in the area to know if it’s a good deal.

If you travel a lot, especially through the same airport repeatedly, become friendly with the rental car service people. Join whatever frequent-customer option your chosen company has because waiting at the counter for an agent can add a lot of time to your trip. Most major rental companies will allow frequent travelers to just walk up to their assigned car, get in, and check out at the security gate. I get an email when I land telling me where my car is, and every little convenience like that adds up.

Oh, and that convertible Camaro SS in the pic? That was given to me with a normal mid-size rental because the guy who ran the lot liked me. He would routinely give me upgrades to Mustangs and Camaros because I was nice to him in a world of people who constantly yelled at him.


I know travel is expensive, and I know saving money is very important, but one of the lessons I learned early on when I paid for my own travel as an independent consultant was that the monetary savings aren’t worth the stress, time wasted, and discomfort.

One of the best things you can do as a traveler is to get status with the airline, hotel, and rental car companies. They will treat you well and your traveling experiences will be substantially more efficient. I know that’s not possible for people who don’t fly regularly, but many of my other tips are. I hope they help someone have a more pleasant and efficient trip.

Safe Travels.






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