The One Simple Pleasure That Makes a Trip Perfect

I don’t aspire to be Gordon Gekko (though I used to have his cell phone more or less, a long long time ago – ever notice how cell phones are one of the great democratizers, no matter how wealthy you are you can’t really get a better iPhone or Galaxy S6?).

I’ll never be ‘rich enough to own my own jet’.

But I do not like to waste time.

I hate checking bags, because I don’t want to wait for them on the back end of a trip. (Not to mention that if something is important enough to bring with me, it’s important enough so ensure I don’t lose).

But I also hate carrying on… because I don’t want to board early to ensure I’ve got overhead bin space, and ideally bin space near my seat.

I’ve long held two propositions:

  • If you’ve never missed a flight you’re spending too much time in airports
  • You don’t want to be the first to board, you just want to not be last.

Still, even if you board somewhere in the middle or towards the end you’re likely to waste quite a bit of time standing in the jetway at least on narrowbody aircraft and US carriers that even use a single forward door to board widebodies.

The most liberating thing in the world I think is not checking bags and not having a rollaboard either. When you don’t need overhead bin space you cruise through airworld nearly frictionless. A laptop bag that can fit underneath the seat in front of you and carry your tolieteries and a change of clothes?

The day trip, and the simple overnight, and the best things going. Can you wear the same pair of pants, same jacket, and just vary the shirt, socks, and underwear? A guy can probably get away with that two days in a row and then hang up the jacket in first class (or in the closet on boarding, or nearly folded up into the overhead bin in back.. just wait for everyone else to stow their stuff so they don’t wrinkle it beyond recognition).

Freedom’s just another word for nothing you’ve got to pack.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. @gleff-

    “I’ve long held two propositions:
    —If you’ve never missed a flight you’re spending too much time in airports…”

    I missed a flight once. I was sitting at an airport bar with my friend, we were enroute to a week in Jamaica and decided to start the party early, before we even got off the ground. Does that count?

  2. I am the opposite (admittedly coming from someone that flies 3-4 times per year). My trip is more important than the marginal minutes spent boarding early. I would rather board 1/2 hour early and fool around on my ipad.

    Additionally, the trips we tend to take (bora bora, hawaii, USVI etc) are for 1-2 weeks and necessitate taking large luggage for snorkel gear etc.

  3. This is my travel style. 🙂

    It helps when your “dress code” is jeans and a t-shirt, though. If you get really good, find a laptop that’ll fit on the tray comfortably even when the seat in front is reclined (think MacBook Air 11″). Add a charger that you can keep tucked away in the bag. Get a bag that’s TSA-approved to keep the laptop in the bag for the X-Ray machine. Take an empty water bottle through security and fill it airside. Finally, make your preferred seat selection (personally, I like the window) that’s not bulkhead.

    Wait until you hit 10k feet. Pull out laptop, attach charger, and pull charger’s cord out for the plug beneath your seat. Everything is well within reach, takes just seconds to pack away, and is in no danger of being crushed by the dolt in front of you or doused in liquids by turbulence (you brought your own free water, right?). You’re set. 🙂

  4. NOT boarding first wastes the most time, while you unnecessarily stand on the jet bridge. Once you are seated, you are free to continue your workaholism…

  5. For those of us that work out though, you need workout clothes and shoes, even on a short overnight. When I was commuting between DC and LA, I had an apartment on both sides and both had enough clothes to last me a week. I would frequently board the plane with just a book and my car keys.

  6. In the 80’s, my father-in-law used to travel with just an old school briefcase – pre-laptop and electronic gadget days. All he needed was a 2nd shirt, socks, underwear, some toiletries, and a portfolio. Life was much simpler then….

  7. When I was a road warrior I had the good fortune of traveling each week to the same destination. I sent my clothes to the cleaners on Thursday evening at my travel “home”, wore jeans and a casual shirt on Friday’s plane ride. Stowed my bag in the hotel closet for the weekend and just carried on my laptop with the week’s undergarments to wash once I got home.

    I was able to wait until the very end to board the plane and easily stow my laptop and fresh undergarments under the seat in front of me. No pressure, no wasted time, it made the entire process so much less stressful. Going to different locales obviously doesn’t work for this but I didn’t have to worry about that. My counterparts used to carry everything with them and struggle with bags, the security lines, the gate area. At least I could control that.

  8. i stopped carrying a laptop or even a netbook once i got my iphone 5. i carry a smaller-sized canvas and leather duffel bag that has lasted me at least 3 or 4 years now. fits right under the seat if bin space is a no-go. i believe in packing as light as possible, doing laundry at the hotel and buying any new clothes as needed. so far, it hasn’t been a real issue.

    the only remote inconvenience i’ve had with packing this way are immigration agents in disbelief that i’d be traveling halfway around the world for two weeks with so little luggage. but even then it just means answering a few more questions than usual. (notable exception: canada.)

  9. Only works for short people, I need every inch of space under the seat in front of me. Even in the exit row/forward cabin.

  10. Not sure what is wrong with being last on the plane (as long as it isn’t WN). I had to check a bag the other week so I only had a small carry on. I gladly waited while everyone else boarded knowing my seat was waiting and I could fit my bag under it. Just sitting in the waiting area is more comfortable than hurrying up to wait in Y. I also respect carriers like Thai that whisk their F passengers to the plane just in time for the door to close. Time sitting on a plane on the ground is some of the least useful or productive in my experience.

  11. The best purchase I’ve made when it comes to travel is my Victorinox Officer 17 wheeled case. It fits everything I need for 2-3 nights away including workout clothes. Fits underneath the seat on regional jets when I take out my laptop portfolio. (macbook air)

    I have a garment bag that fits 2-3 shirts and an extra suit. It’s a stretch for 4 nights, but it’s better than checking a bag or gate checking anything.

  12. It helps tremendously if you don’t care what you look like. I’m hardly vain, but I’m not going anywhere without a curling iron, make-up, nice clothes and shoes and casual clothes and shoes. That’s the first 24 hours, and only petit women with small feet can get that in a carry-on. Checking bags is just part of the price of travel for many of us.

  13. The other benefit of foregoing the rollaboard is not having to gate check on regional jets (which sadly almost all my trips begin and end on). For weekend trips, I just use a gym bag.

  14. And one wonders why Americans are universally stereotyped as horrible dressers.

    You state you’re wearing the same crumpled-up pants you’ve traveled in for your meetings on the following day, instead of some clean, crisp ones from your baggage? I am in disbelief, but I have a feeling that you actually do that.

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