I knew I had to go on a Very Long Trip the day the internet erupted in outrage over Twitter’s decision to shift the shape of its “fav” button from a star to a heart. What started as a fanciful daydream cemented further when I found myself dreading the darkness of winter ... in June. It hardened into stone when I turned 30. For me, the decision to temporarily drop out was thanks to a confluence of nominal events that piled up on top of each other until it became clear that the current trajectory of my life was no longer tenable. Maybe something similar has happened to you. Maybe something terrible has happened to you. Maybe nothing at all has happened to you, but it’s been too long since you dusted off the old rucksack.
The good news is that if you pack correctly, your Very Long Trip could end in a book deal, which will then be optioned into a Hollywood blockbuster. But that’s a big if: It’s unlikely that things would have turned out nearly as well for either Julia Roberts or Reese Witherspoon if they’d attempted to forge plot-enriching friendships dressed head to toe in nothing but Scotch tape and a bandolier loaded with “essential oils.” (“Sorry, lady,” the locals would say, holding their noses against the overpowering stench of bergamot. “You’re on your own.”)
Of course, what you should bring on your Very Long Trip is mostly dependent on where you’re going. Three months sipping red wine in the 4th Arrondissement is quite a bit different than three months slogging through dense Amazonian rainforest. But there are some rules of thumb that apply to everyone not able to afford their own personal porter ... yet.
You will initially be tempted to cram as much as you can into your bag, certain you will find use for each and every scarf and piece of flatware in your apartment. If you’re backpacking, outdoor stores are a phantasmagoric toyland for the aspirational adventurer. Do not let yourself be sucked in. Pack for two weeks. That’s it. Two weeks. If you’re on a multi-month journey, you will do laundry, just like you do at home, in ’Murica. If you’re going somewhere especially rural, pack a little bottle of biodegradable detergent.
But if you simply can’t resist the mellifluous siren song of the outdoor store, sate yourself with a headlamp and a quick-drying towel. If you’re traveling in the developing world, these items will save you. Scenarios!
You’re staying at what passes for a perfectly nice hotel or hostel, but the towel offered by the proprietor looks like it played a supporting role in a live birth. Oh, and look at that, it’s (still?) damp. You go ahead and put your face on that if you want, but me? I’m unrolling my towel. BUT NOT JUST ANY TOWEL. While Douglas Adams and I are in total agreement on the towel as emergency blanket, distress signal, and weapon, normal beach towels are not only extremely bulky, they also absorb water like a motherfucker and stay wet for eons. Quick-drying towels can fold up to roughly the size and weight of an empty beer bottle and dry out in a matter of hours.
I also cannot overstate the importance of the headlamp. Are you on an overnight bus ride and unable to sleep because your seatmate’s chicken won’t stop crying? Perhaps you want to read your book. Did the electricity in the coastal town you’re visiting go out, and your attempts to get a sense of a timetable are met with a a contemptuous shrug? A headlamp is vastly superior to a normal flashlight, because it frees up both hands for whatever you want to use them for, whether it’s digging around in your bag for your earplugs or waving them around in despair after realizing you dropped your last contact lens on the dirt floor.
Bonus item: a compass. “But my phone has a compass!” Yes, but your phone could get stolen, fall in a river, fall in a python, or fall off the Great Wall because you chose to take your selfie during a thunderstorm and it slipped. Get a tiny one and clip it in your bag or pocket, and you will be at least 48 percent less disoriented at all times.
I realize this is 2016, so it’s probably been several years since your hands alit on an actual book, but in all likelihood, you will find yourself in situations where you will want to read, like when the internet shits out (which it will) and you can’t watch Bojack Horseman on Netflix.
Moreover, while very charming, books are heavy dead weight that, frankly, you haven’t got the space for. A Kindle weighs the same whether you are reading a Buzzfeed listicle or The Power Broker, and doesn’t require the internet to use. I’m no Amazon shill, but I’ve found mine to be extremely useful.
This can be difficult if you truly have no idea what you’re getting yourself into. This may seem obvious, but check the weather in the places you suspect you might be going. Just because you’re venturing to what’s generally considered a warm climate doesn’t mean you should forgo all pants. (Definitely bring at least one pair of pants.)
If you’re planning to do any specialized activities, like rock climbing or cycling, plan to leave your own gear at home and rent when you get there, unless those activities are a cornerstone of your trip. If possible, everything you pack should be suitable in at least a few situations. Outdoor stores sell plenty of moisture-wicking men’s hiking shirts as appropriate for the trail as they are for Tinder drinks. For women, assembling a wardrobe that’s both functional and not ass-ugly takes a little more effort, but is not impossible. Prana has some items that aren’t utterly emetic. It’s boring, but neutral colors you can mix and match will help stave off Outfit Burnout.
Leave your fancy rings, watches, and bolo ties at home, as losing them will not only be devastating, they will make you targets for theft.
As you pack each item in your bag, imagine not having it anymore. How upset are you? Is it crushing? Leave it. I once attempted to ship a duffel bag back to the States from Hungary, which I should have known was a doomed endeavor from the postal worker’s glazed expression and the fact that he charged me only around $50, a price the bored teenage employee seemed to have pulled out of thin air. In that bag was a vintage dress that looked better on me than any other garment ever will, and I never saw it again. It’s been a decade, and I still sometimes think wistfully about that damn dress. It may have taught me the importance of non-attachment, but fuck that. It made my arms look great.
Checking a bag is less than ideal these days, because in addition to the ever-grinding concern of it being chucked carelessly into the abyss by a bag handler, it also often costs money. That said, if you’re traveling for longer than a month in a rural area, you may very well want some items verboten on the plane, like a pocketknife or a gallon of artisanal mayonnaise. If that’s the case, just check the bag. Let the sweet relief of powerlessness buoy you as it disappears down the conveyer. Assume you will never see it again, and that your reunion on the other side will be a delightful, unexpected surprise. (You will see it again.)
A checked bag means the contents of your carry-on become crucial. Consider any critical medications first, followed by items that will make you exponentially more comfortable. Your toothbrush, an extra pair of underwear ... whatever accoutrements are mandatory to make you feel like a human and not a pile of damp garbage wearing a neck pillow.
With limited exceptions (North Korea, Cuba for now), anything you forgot or broke or lost can be replaced. It’s never ideal to have to spend hard-earned cash money on items you’d already bought once, but you may as well accept now that it will probably happen. Factor these losses into your budget, and remember that they’re factored in once you’re forced to replace things. Think about the items you know you don’t want to lose: I have an excellent but rather pricey jacket, for example, that I would probably commit seppuku over if it disappeared on a bus. I intentionally got it in a bright color as a defense against my own absentmindedness, but it remains the one object that I consciously take care to note whenever I’m throwing things into a bag for a 3 a.m. departure. Which leads me to another point.
Things get forgotten in the throes of panic—the one shoe that gets left under the bed, the drawer you neglected to check. The extra 15 minutes of sleep is ultimately not worth it when you realize you left behind your one pair of pants. If you’re planning on drinking heavily before you take off, make sure you run extra defense. Lay out your travel clothes before cracking the first beer, and organize everything else into your bag. Drunk You will be so impressed by the forethought of Sober You, you’ll be able to celebrate with another shot!
“I’m sure it will be fine” is a sentiment that’s anathema to the savvy traveler. Let me assure you that if you forget your visa, it will decidedly not be fine. A friend—one of the most well-traveled people I have ever met—told me that she was once sent straight back to the States after touching down in India because she’d gotten a new passport, and her visa was still attached to her old one. “Not an experience I want to repeat,” she said in an email, securing her title as the grand empress of understatement. Ditto immunizations: Check the CDC website well before your departure date, as some vaccines consist of a series to be completed over the course of a month or more.
While you should obviously bring any prescription medications you need, have the basics in your carry-on as well. The CDC offers a good if perhaps overly comprehensive list (bicycle helmet??!), but take very seriously the over-the-counter portion. If you find yourself thrashing around in the middle of the night gripped by a fever or stomach ailment, you won’t be able to call your winter boo to make a midnight run to Duane Reade for you.
Things will break, things will go wrong. Buses will be missed, you will get sick, perhaps you’ll get robbed. You can allow these maladies reduce you to a whimpering man-tissue, or you can take them in stride and start fashioning them into the yarns you’ll tell your friends once you’re safely back home. Or better yet, the script you’ll hand to ... Scorsese? Bay? Is this the script that the Academy will finally deem worthy of reviving the cryopreserved corpse of Orson Welles? COULD BE.
On one of my first days traveling in South America, where I will be for the next three months, I awoke to a text from a friend in New York telling me that David Bowie had died. I fumbled for my laptop and dressed to “Under Pressure,” surely the exact same ritual I would have performed had I been waking up in Brooklyn, and the exact same ritual that my countrymen back in New York were performing themselves. Having access to the music that makes you feel Normal isn’t so much a suggestion as it is a tool for survival.
Still, when homesickness inevitably sets in, it’s nice to have some tangible objects around which to wrap your fingers while you await the low point to pass. It shouldn’t be expensive (see above), but simple and comforting. Mine is a journal stuffed with letters from friends, which sounds cheesy as hell and most certainly is. But. Regardless of the impetus for your Very Long Trip, there will be times when you will need to let yourself be maudlin and overwrought, because you are not a robot, because you are homesick, because you are scared, because you miss consistent hot water and high-thread-count sheets, because you are occasionally seized with nostalgia for your walk to and from the subway, and the very comforts that eventually hardened into ennui that made you take this journey in the first place. Hold your little treasure close and watch something grotesquely slapstick on Netflix, if Netflix is available. The avalanche will pass.
Lauren Evans is a freelance writer spending the winter in South America. Follow her on Twitter here.
Art by Sam Woolley.