How to Pack Like a Seasoned Pro for Super-Long Trips

Last June, I spent a month traveling across Iceland and then hopping around the Greek isles while reporting stories for InsideHook. (I know, tough life but somebody has to do it.) While it wasn’t my longest stint on the road, the combination of climates, activities, and locales made it a bit of a tricky one to pack for. Especially since I have one non-negotiable rule while traveling: I refuse to check a suitcase. Unless I’m returning home with invaluable whisky stashed away, that is. Now, with the help of some fellow trusted travel pros, we’re bringing you the secrets of traveling light and traveling well, no matter how long you’re gone for — or even if you don’t know how long that might be.

Embrace Carry-on Life

There’s no better feeling in the world than stepping off an airplane and walking straight out of the airport. No more waiting, and no fear of a bag not arriving with you. There are other advantages, too.

“The less stuff you can pack the better, even if you’re only going to be in one place for a long time,” says Natalie Compton, a travel reporter for The Washington Post’s By The Way. “Traveling with just a carry-on saves you the hassle of schlepping heavy bags in and out of Ubers, up and down stairs, in and out of hotels. If you’re strategic with your packing, you’ll find you can get away with bringing less.”

The key is paring down as much as possible, and once you start stripping away the nonessentials, you’ll realize that’s exactly what they are. Nonessential. Marie f’n Kondo your packing list. Ask yourself, “Does that third pair of jeans really spark any joy?” We didn’t think so. Prioritize reusable clothing items, layers, and solid colors that work well in different combinations and settings. If you need a jacket or a blazer with you on your trip, plan to wear it on the plane.

Live on the Road: Shop, Do Laundry

When you’re traveling like a nomad, there’s no way you could literally pack everything you need, be it clothes, accessories, or other supplies. So don’t try to. You can’t bring four or six months of clothes and toiletries with you, so does it really matter if you have 10 or 14 or 21 days worth of gear with you? Therefore, another way to lighten the load is to realize you can get what you need when and where you need it.

“If I’m packing for a long trip I focus on and double check I’ve got the difficult to replace things,” says Alex Outhwaite, a travel TV presenter, who spoke to us while backpacking across South America, and planning a group trek in the mountains of Pakistan this fall. “Passport, any unusual medication or contact lenses and expensive tech, everything else can be easily bought on the road. This alleviates any worries that I’ve forgotten things.”

My list of most-essential accessories includes my passport, and these days vaccine card, with a digital copy of both on my phone. That’s a phone with a charger and a travel outlet adapter, so I can plug in anywhere in the world. Throw in my Surface Pro, a backup battery, and everything else is negotiable. Some months it might be my DSLR camera and a telephoto lens. In other instances, it might be hiking gear, or when I know lots of busy days and city hotels are on the docket, TRX straps, so every hotel room is a gym when I need it to be.

Just as you can pick up what you need on the move, you can also take care of the chores which extend a single suitcase into months worth of clothes. “Be strategic with where you’re staying,” Compton says. “Can you find an Airbnb with a washing machine? If not, can you find one within walking distance of a laundromat? The latter may sound like a hassle, but some of my most memorable travel moments are from finding places to clean my clothes abroad.”

When in doubt, or desperation, a few individual use packets of laundry detergent and a hotel sink can be a life saver. “I’m also a fan of traveling with quick-dry workout clothes like running shorts and sports bras so I can pack just one of each, haphazardly wash them in the sink after each use, and have them dry when I need them next or have to my hotel or Airbnb,” Compton says.

…and Travel the Way You Want to Live

If you’re on the road for an extended period of time, then you should be traveling the way you want to live, and holding onto the same ideals and principles. For James Thornton, the CEO of Intrepid Travel, that means keeping sustainability front of mind with all of his endeavors. “It’s always exciting to pack for a trip and there are some great B Corps out there that can help you reduce waste on your travels,” he says. Thornton should know, as his company recently recertified as a B Corp, and is recognized as the largest travel B Corporation.

“Living in the world’s coffee capital Melbourne means I love my daily caffeine fix and popping a KeepCup in my bag means I can avoid takeaway cups while on the road,” Thornton says. “I’m also a huge fan of fellow B Corp Patagonia – their gear is really high quality, plus you can get it repaired or altered, extending its life, and keeping it out of landfill.”

He’s not the only one who values proper caffeination while on the road. For globetrotting Irishman Philip Duff, the founder of bartender-favorite Old Duff Genever, traveling the way he wants to live means looking the part regardless of his environs, and having the energy to pound the pavement as he zigzags across up to forty countries per year teaching seminars on spirits and cocktails, promoting his brand, and consulting for others. “There are two things that are always in my luggage, even when it’s a carry-on: my HiLife hand-held clothes steamers – I actually own two, one for US voltage and one for the rest of the world – and my Wacaco hand-held manual espresso machine,” he says.

“Steamers mean you can look immaculate in return for just three or four minutes steaming each morning, even if your jacket and shirt have just come out of a suitcase, or you’ve just come out of a dive bar,” Duff continues. “And no matter where you are, there’s no better way to start the day than with a great espresso. The Wacaco doesn’t even need electricity, just hot water – and it means you can avoid the dreaded, ancient hotel-room instant coffee!”

Versatility is Crucial

Any item, be it a piece of clothing or a must-have accessory, is exponentially valuable if it’s versatile and usable in different ways, or for different reasons. “I always travel with a large, light scarf,” Outhwaite says. “It’s helpful for covering up in churches and temples, dressing up a casual outfit, using as a beach throw, or even keeping warm in excessive air conditioning.”

For Compton, when she sees a red piece of clothing, she wants to dye it black. “When I was a freelancer, I’d end up spending months on the road at a time, and the best practice for my long-term travel was to wear almost exclusively black clothing,” she says. “Like, a lot of it. All over the world, black. Black clothes tend to look a little dressier, show less dirt or spilled food or sweat, plus you can wash and dry it all in the same laundry load. A black Everlane t-shirt can double as your daywear and your workout gear.”

At the end of the day, packing and living like a travel pro is part art, part science, and part skill honed through repetition, mastered only with extensive experience. The weekender? That’s for the beginner. The week-long conference-to-beach jaunt? Worth a yawn. The three-month, multi-continent rove with a carry-on? That’s a worthy opponent, and like any good opponent, it’ll help you raise your own game. Now on my mark, get out there and pack your bags, gentlemen.