Packing 1 Small Carry-on for 4 Months on the Road

Rich and I take the same amount of luggage for a weekend or many months on the road.

“Good grief, what happened here?!?”
 
I stared aghast at what remained of my gray cardigan, recently purchased for our upcoming trip and washed for the first — and last — time. I’d scrupulously followed the instructions on the label, yet the once-long, flowing garment was now short and boxy, with arms that would be snug on a ten-year-old. As directed, I attempted to “reshape and dry flat,” but after every tug, the cardigan simply sprang back into its preferred chunky-child size. I could almost hear it snickering at my futile efforts.
 
When you’re living out of a single small suitcase for months at a time, every garment has to pull its weight, fitting over and under various other layers. Tight clothes are impractical, and that goes double for us at the moment, when we’re about to depart on Our Mediterranean Comfort Food Tour. Serious eating will be taking place, and while I’m hoping my weight won’t skyrocket, I doubt that my arms are going to shrink back to the size they were in fourth grade. RIP gray sweater.

The late, great gray cardigan. A major US department store has some ‘splanin’ to do.

​Whenever Rich and I set out on one of our big journeys, such as the one that inspired my book Adventures of a Railway Nomad, our Luggage-Free experiment, or Our Most Unplanned, Disorganized Trip Ever, people ask me all sorts of questions about what we're taking along. So let me start by saying that we’re not going luggage-free this time; for months on the road, I like a few more creature comforts than I can fit in my pockets. But I am keeping baggage to a minimum: just a single small roll-aboard, plus a roomy shoulder purse, mainly for sweaters, maps, and water bottles. I keep valuables zipped safely inside my travel vest. 

This is the typical amount of luggage I take everywhere.

​Rich and I take the same amount of luggage whether we’re going away for the weekend or many months. We pack a few changes of clothes, a spare pair of shoes, a rain jacket, loose trousers for sleeping and yoga, basic toiletries, and essential electronics. We’ll do laundry frequently (although not every night, as we do with luggage-free travel) so we don't need tons of clothes. Comfort is the top priority, although we maintain what we hope is a reasonable level of stylishness as well.
 
For Rich, this always means choosing a signature hat for the trip. Fedoras and Panamas are an integral part of his personal style, and a month ago, he began scouring Seville’s hat shops in search of something new. 

 
​As we strolled around from shop to shop, Rich and I discussed a riveting show we’d just watched called Minimalism: A Documentary on the Important Things. “So much of our lives are lived in a fog of habitual behavior,” says author Dan Harris in the film, against a background of Black Friday madness. “We spend so much time on the hunt, and nothing really does it for us.” Later Shannon Whitehead comments, “The status quo in the fashion industry right now is driven by fast fashion. Maybe when our moms were shopping for clothes, or our grandmothers, there were four season a year…Now we work in a cycle of 52 seasons per year. They want you to feel like you’re out of trend after one week so that you will buy something new.”
 
“Can you believe it?” I said. “They’re trying to manipulate us into buying stuff we don’t really need.”
 
And then the irony struck us.
 
“What would you think if I took my old coffee-colored straw hat?” Rich asked.
 
“Works for me.”

Rich's spring hat is the color of café con leche (coffee with milk); it's one of my all-time favorites.

So the question of Rich’s hat has been settled.

​As for me, the most vital issue is always, “What's going on my feet?” 

A new pair of walking shoes, an old pair of comfy sneakers, and slippers

As for my clothing, I am bringing a variety of garments in neutral blacks, grays, and whites, with some summery blues and greens, and a pair of wine-colored trousers for a pop of color.

By far the heaviest things I carry are my electronics, toiletries, and prescription meds.

Toiletry kit, pouch with medications, small laptop, iPhone, Kindle, reading glasses, notebook

Beyond that, I will be tucking in miscellanies, such as a sleep mask, spare eyeglasses, socks, and underwear, but I suspect that you are already familiar with such items and don’t need detailed instructions from me regarding how to pack them. If you do want to get down into the deep details, I have a Packing page on this website, where you’ll find such articles as Packing Extra Light, How to Choose Great Travel Clothes, Rich’s World Famous First Aid Kit, and much more.
 
The best way to pack light is to remember that you don’t have to prepare for every single contingency that might conceivably arise. If the president of Albania invites us to a black tie gala, or we get tickets to a Rolling Stones concert and feel edgier attire is required, we’ll have the fun of shopping for it on the spot. I’ve learned that just when I start thinking I should have packed a sun hat, some enterprising local is standing there offering an armload of Panama knockoffs.

Yes, I’m still bitter about the gray cardigan, and when I get back to the States a major department store has some ‘splanin’ to do. But I have no doubt that somewhere along the route, a perfect replacement is just waiting for me. I look forward to making its acquaintance, and have vowed not to wash it until the trip is over.

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Do you have any great packing tips or luggage disasters to share? I'd love to hear them!
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