This scene from Joe vs. The Volcano captures the dilemma all frequent travelers face: Getting your stuff from Point A to Point B. As the luggage salesman says, "Out there, it's just you and your luggage." Overnight trips aren't a problem...throw a shirt, underwear, and socks in the Adventure Bag and I'm good to go. Two to three day trips are equally trouble-free...extra clothes in a small, carry-on bag and the Adventure Bag with its usual collection of gear suffices nicely.
Now, when I say small, carry-on bag, I really mean a small bag that I physically pick up and carry on the airplane...and "small" means it takes up about a quarter of an overhead bin. This, I recognize, is in marked contrast to the three other major classes of "carry-on" luggage: backpacks, shopping bags, and wheelie bags. I accept day packs as perfectly legitimate carry-on luggage and have, on occasion, resorted to using one. However, to men who travel wearing a suit and a back pack: "Buy yourself some 'big boy' luggage and grow up." Also note that I specify "day pack" here. See that overhead bin, Sparky? Only a third of it is yours. The rest belongs to your two seat mates. They may choose to use it or not. That is their prerogative as a fellow passenger. Don't presume to make the decision for them by being a selfish asshole and throwing your big-ass piece of luggage up there.
Shopping bags are an unfortunate, but sometimes necessary, piece of carry-on luggage. However, I have to say that if you find yourself using plastic grocery bags as carry-ons on even a semi-regular basis, you really need to rethink your travel strategy.
Wheelie bags. Wheelie bags are one of the most diabolical evils ever foisted upon the traveling public...and, like most diabolical evils, it, at first, seemed to be a good thing. A bag, with wheels and a handle, that you wouldn't have to carry, just pull behind you like a grown-up version of a little red wagon. What could be better? Why nothing, nothing at all...until you have a plane full of people trying to maneuver their bloated wheelies down a narrow 757 aisle and heft them up and stuff them into an overhead bin. The GI's in World War II presciently invented the word "blivet" to describe this situation...and men, if you are young and in good health, and I see you trotting down a concourse with a little wheelie carry-on bag trailing behind you....well, let's just say that I have to assume you are flying off to see a Cher concert and your wheelie contains your "in-drag" costume. Man up, bro.
Having said all this, on extended trips when I have to check luggage, for years, my "go-to" bag has been a Land's End duffel that has served me long and well:
I have survived for multiple weeks out of the contents of this bag...and had enough extra room to pack trinkets for family members for the return trip (Attention female relations: Those Prada bags you're sporting around came back from Shanghai in this bag). But there's a problem here. After a few trips of lugging this bag through the Frankfurt airport through tunnels like this:
So, after having just lugged my Land's End duffel through the Honolulu airport, I decided I needed to buy a wheelie bag I could check. After doing a lot of research, I've decided on this one, (Click on the "fit1" picture) because sometimes, the redhead likes to travel with me.