The Secret to
Traveling Well

A diehard carry-on-only guy discovers the joy of skycaps

Vintage airplane travel

Time tends to move strangely at the airport. People downing beers at 10:30 in the morning isn't an uncommon sight. Shops and restaurants close inexplicably early. And minutes never move slower than the painful transition from landing to disembarking your plane. I think this is why I became a diehard carry-on evangelist. It offered complete control and minimized the threat of having to wait. Because if you check a bag, you've got to wait to check it in, you've got to wait at your destination's baggage claim and then there's the fear of having everything get lost in the vortex of missing luggage.

Of course, carrying on comes with its own stresses to contend with. You have to jockey for suitcase space in the overhead bins—real estate that has become increasinly in demand these days. And you've got to be a master packer to efficiently stuff everything into a smaller bag and successfully get it through security. But that seemed like a small price to pay to ensure I wasn't “inconvenienced” with having to wait around.

But a few trips ago, I didn't have a choice. I was flying overseas and going to be gone for over 10 days. I wanted to bring my regular toiletries and I needed to make sure there was enough space to bring home some of the stuff I knew I wanted to buy while I was traveling. I would need to check a bag—a big one.

And then the most amazing thing happened. Instead of having to lug all my stuff through the airport, I checked into my flight and handed over my suitcase before heading to security. With only a backpack on, I was suddenly free. The security line was easier. I could roam throughout the terminal unencumbered, grab a coffee and peruse some magazines before strolling to my gate. And while the gate agents warned that our “completely full flight” wouldn't allow everyone's bag to fit in the overhead bin, I sat back and relaxed, knowing it didn't matter to me.

I brought that less frantic mind-set with me once we landed. I knew I had time before our luggage was spit out onto the conveyer belt, so I took care of myself. Went to the restroom, freshened up and then grabbed a quick snack. By the time I made my way to the baggage carousel, our bags were just starting to parade in front of my fellow travelers. Less than 10 minutes later, I had my bag and was in a Lyft.

I realized that my fear of waiting was simply fear of the unknown. Now that I knew the slight wait was entirely worth the obvious benefits, I wanted to go even further. On my next trip—newly emboldened—I packed my big suitcase and embraced the airport move of a previous generation: curbside check-in.

Sure, it seems like an indulgence or an archaic waste of time in an era of online check-in and self-serve kiosks, but I discovered it's the savvy traveler's amenity hidden in plain sight. Why fight the possible lines and mobs awaiting you in the terminal when you can get out of the car, hand your bags and ID to a skycap and be done with it? They'll get your bags squared away and can print out a boarding pass if needed—and for most major airlines there's not even any extra fees. You simply tip a few bucks per bag—a small price to pay for the convenience of unloading your bags before even entering the terminal.

If that's not incentive enough, I can confirm that sky caps are much more lenient than ticket agents inside when it comes to baggage weight restrictions. And maybe it's the ability to work out in the fresh air or the regular tips, but skycaps also seem to be in much better moods than the agents inside. Or perhaps it's just that less people utilize them. But I'm glad I'm one of them now.

Tag Your Bag

A luggage tag can almost seem irrelevant in this carry-on age, but they’re definitely necessary when you check your bag. Plus, they’re an excellent way to flex your style and help you quickly identify your suitcase on a baggage carousel crowded with lookalike black bags.

Boarding Pass Custom-Stamped Leather Luggage Tags

Custom-stamped leather luggage tags,
$89 for two by Boarding Pass

Leatherology Signature Leather Luggage Tag

Signature leather luggage tag,
from $40 by Leatherology

Orvis Engraved Brass Luggage Tags

Engraved brass luggage tags,
$49 by Orvis

Ghurka Personalized Brass Tag

Personalized brass tag,
$195 by Ghurka

Dynotag Web-Enabled Smart ID Tag

Web-enabled Smart ID tag,
$19.95 by Dynotag

Clare V. Leather Luggage Tag

Leather luggage tag,
$55 by Clare V.


While most bags make it back to their owners, the airline industry still dealt with nearly 25 million lost or stolen suitcases in 2019, according to Sita, an international IT provider that monitors global baggage handling.

The Smart Way
to Start Your Day

The Daily Valet. is your cheat sheet to what's happening, what's cool and what's making headlines. It's your secret to being the most interesting man in the room.

More on
Traveling Well