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Now that I have the flexibility in my remote-work career and the income to buy plane tickets more often, I'm making the most of it. I love to travel, but I hate hauling all my shit from place to place just to live somewhere new for a bit. Here's what I've learned in my efforts to travel light while keeping my creature comforts (read: my computers) with me.


Left to right: 24 oz ThermoFlask, 25000 mAh USB-C powerbank, hanging toiletry bag

As I've gone beyond my twenties, I've realized that my mom, with her big shoulder bags full of water bottles, wet wipes, and snacks, was right: the worst thing that can happen to you as a full-grown adult is to be caught lacking. So the core of my packing strategy is self-sufficiency. I should never find myself running around to find something I need which I could have brought with me. My big needs are water and power.

I love my insulated 24 oz ThermoFlask which can keep my water ice-cold overnight, and these days it doesn't leave my side – doubly so when I'm abroad. Any day that I need to pop into a shop to grab a bottle of water is a day I haven't prepared properly.

These days, between my boarding pass, my music, and my movies for the flight, my phone is critical to me too. Life is too short to live on Low-Power Mode, so I keep a 25000 mAh USB-C powerbank on me for longer trips. This thing has enough power to keep my phone and (M1 Air) laptop going for days, and I've never regretted hauling it with me. I'm religious about keeping all of my batteries topped up.


To hold my toiletries, I use a hanging bag with plenty of space for everything I could need, including medication and mouthwash. For shorter trips or one-bag travel, I use a smaller, lighter hanging bag.


The drugs I typically bring with me are:

  • Melatonin: for solving jet lag by helping me get to sleep on schedule to arrive in a new time zone. Aligning my sleep schedule to avoid losing a day to travel is my favorite party trick, and it never fails to impress anyone over 30.
  • Benadryl: for occasional allergies, and it doubles as a much stronger (occasional) sleep aid than melatonin. Great for when you've been out later than you intended but you still need to catch a 7am train tomorrow morning.
  • Aleve: never leave home without painkillers.


Left to right, top to bottom: Trtl pillow, SleepSloth eye mask, Laser Lite earplugs, Sony WH-1000XM3 noise-cancelling headphones

I'm a person who can fall asleep anywhere if I'm tired enough, but sometimes I still need a little help. So these are always in my carry-on:

  • Earplugs: My favorites are the Howard Leight Laser Lite disposable foam earplugs. They're extremely comfortable and cheap, they're reusable for a few days if you keep your ears clean of wax, and they block out a ton of sound if inserted properly.
  • Eye mask: I love this SleepSloth eye mask, which blocks out all light and doesn't put any pressure on my eyes. You can even comfortably open your eyes underneath it.
  • Trtl pillow: This adjustable neckscarf-style pillow provides support to keep you from "nodding on" as your head tips over sideways. It's also incredibly compact compared to a big fluffy neck pillow.I've slept dozens of hours with this strapped to my neck on long trips, and it only makes you look a little silly. (They're mostly just jealous of you.)
  • Noise-cancelling headphones: The Sony WH1000-XM series provide incredible noise cancelling, even if you're frugal like me and find a deal on an older generation. I used to be a die-hard Bose QuietComfort fan, but I had two pairs go out on me out of warranty and I no longer trust the brand's quality.


Left to right, top to bottom: Under Armour technical shirt, tabi slippers, synthetic stretch chinos, Fun Toes merino wool socks, Timberland Mt. Maddsen hiking boots

Never skimp on anything that separates you from the ground. It's critical to bring a pair of shoes that won't let you down when you're away from home. Shoes are heavy and bulky, so if you bring one pair that will get you through everything, you won't have to fit a second pair into your luggage.

Look for something durable and hard-wearing. Outdoor hiking boots are a great option, and high-quality brands (with varying levels of everyday style) include Keen, Merrell, Red Wing, and Teva. I am extremely partial to the Timberland Mt. Maddsen boots, which look amazing and are fully waterproof – I've even brought these on canoe trips. I typically wear these with cheap merino wool socks, which are comfortable in hot and cold conditions as well as breathable to keep sweat off your skin.

When you're lounging indoors, you'll want some shoes to grip the dirty floors and protect your nice socks from them. Look into tabi-style slippers, which are lightweight, easy to wash, and fold flat into your luggage.

To stay comfortable when you're spending several hours sweating into your seat on a bus, an airplane, or in an airport chair, I recommend you pack only high-wicking synthetic technical shirts. They double as great shirts for hiking or walking around a city, they don't wrinkle, and they move the sweat off your skin. Anything will do, so find a brand that you find comfortable which fits you well. (I like these shirts by Under Armour.)

Pick shirts that are all around the same color – coordiating your outfits is much easier when all your shirts and sweaters match all your pants. If you're going somewhere sunny, look for long-sleeve technical shirts with built-in SPF protection.

Science has made incredible advances in stylish, wrinkle-free, everyday pants. Synthetic stretch chinos are so comfortable you'll forget you're stuck in a plastic chair for seven hours during your layover, and they're stylish enough to shame everyone else showing up to the pub. I love these so much that next time, I'll bring a second pair instead of my denim jeans.


Left to right: Fire Stick 4K Max, Peak Design Tech Pouch, Anker PowerExtend adapter

I spend a lot of my downtime on vacation catching up on my favorite TV shows and websites, so it's important to me that getting power isn't a pain in the ass. It's critical if I'm working remotely!


An outlet extension strip is an incredible thing to have with you when power outlets are limited. No need to snipe an outlet or wait for one to free up – just piggyback their adapters onto yours and you can plug in too. This Anker PowerExtend adapter triples as an extension cord, a power strip, and a USB-C PD charger for my MacBook, which makes it totally indispensable to me.

If you're going somewhere with different plugs, don't forget to bring an outlet adapter. A 240V -> 120V adapter is often huge and heavy, so if you can avoid bringing one of these, don't bring one! Odds are your USB adapter (e.g. the Anker listed above) supports anywhere from 100 to 240 volts AC – you can find out for sure by reading the fine print on the back.

And of course, don't forget the USB power bank I mentioned under the Essentials section.


Triple-check to make sure you have the correct cables on you for all your devices before you leave. It's never a great feeling to leave on your trip only to have to hunt down an overpriced Lightning cable at the airport. And if you're planning on using your iPhone as a mobile tethering modem for your MacBook, make sure you bring that pesky 3ft USB-C to Lightning cable too.

If you carry as many cables and devices as I do, you'll want to organize them better than coiling them all up and tossing them into a big pocket together. The Peak Design Tech Pouch is the gold standard for organizing lots of little cables, but of course, it's just a pouch with pockets! There are plenty of $10 options which do the job just fine.


I love catching up on my TV and movie backlog while I'm on vacation, but I hate showing up to a rental apartment and finding out their smart TV is all goofed up, or the HDMI cable is broken. So these days I bring my Fire Stick with me on trips, along with its power adapter and cables, in a little accessory bag. It stays signed into my streaming accounts and makes it easy to put on whatever I want when I arrive.

Amazon devices like the Fire Stick regularly go on sale during holidays and Prime Day, so don't buy one at full price.


A great trip ends when your luggage goes missing. The best way to prevent this is to never let your bags leave your side – that means no checked luggage! There are two main schools of thought:

1. One-bag

Left to right: Osprey Farpoint 40, Aer Travel Pack, Peak Design Travel Backpack

Pack all your stuff into a single bag.

Aim for a 40L backpack intended for carry-on travel. Bags of this volume will fit on airplanes, either below the seat or in the overhead compartment. (In my experience, they even fit onto Ryanair.) A bag listed as a travel pack will typically unzip all the way around so that you can pack it like a suitcase, rather than stuffing in from the top like a hiking pack. My favorites are the Osprey Farpoint 40, the Aer Travel Pack, and the Peak Design Travel Backpack.

If you only bring one bag, your one bag never leaves your sight (or your arms) so it's at reduced risk of being left behind or stolen. Airlines love you – many offer priority boarding for folks with no overhead carry-on, and you're never at risk of having to check your second bag when the plane is full. However, you will have less space for all your items.

Folks who are willing to pack light can absolutely do a trip of any length with a very minimal set of clothing:

  • 3-4 shirts, sets of underwear, and pairs of socks
  • 1 pair of versatile pants
  • 1 pair of comfortable pants (or shorts) for sleeping and lounging
  • 1 all-purpose down jacket
  • 1 versatile sweater layer

This gives you enough clothing to wash your dirty laundry in a sink and hang dry every couple of days. You can bring travel detergent packets, or you can just put a bit of your own detergent into your travel shampoo bottles – it's the same stuff.

2. Backpack and carry-on

Left to right: Travelpro Maxlite 5, Briggs and Riley Domestic 56cm, Peak Design Everyday Backpack strapped to a carry-on handle

Pack your clothes into your carry-on bag and your devices into your backpack.

A one-bag travel pack can turn you into a tortoise, and they're not ideal for bringing your laptop to work from a coffee shop. If you choose to bring a carry-on, you can bring most of the clothes you want, and you can bring a backpack that's more ergonomic for daily use. Plus, you'll have more cargo space for bringing souvenirs for friends back home.

If you go this route, bring your favorite daily backpack and a good softshell carry-on. Mine is the Peak Design Everyday Backpack, which comes with a handy built-in strap that fits over a carry-on bag's handle. You do not need a hardshell carry-on – hardshells are most useful for protection against airline employees chucking your bag into the cargo hold, and softshells allow you to use more space and expand the bag's capacity with a zipper.

Pick a high-quality spinner (four universal wheels) carry-on bag. It should either come with a lifetime warranty (Briggs and Riley) or be cheap enough to replace when the wheels go out in a few years (Travelpro Maxlite 5). Don't forget that American brands have a "domestic" size (larger for American plane cabins) and an "international" size (smaller for European plane cabins), so size according to the airline you usually fly.

Other bag tips and tricks

Left to right: Gonex compression packing cubes, crossbody sling, 4Monster 16L packable daypack

I am deathly afraid of being made a target when on vacation, especially when I'm out drinking. I'm also horribly scatterbrained and liable to lose anything not physically attached to me. So I keep my passport, wallet, and cash glued to my body using a crossbody bag. (It has enough space for an N95 mask and my AirPods as well.) I like this bag enough that I've started using it for my dailies at home, rather than transferring all my items between my pairs of pants every morning.

Sometimes I just need a bag to hold my down jacket and water bottle, or a tote for groceries, and it's inappropriate to bring my nice laptop backpack. So I always bring a 16L packable daypack in my luggage. It packs down into a tiny bundle that I can shove into any free corner of space, and it's ultralight when empty.

Whichever bags you use, you can get more volume from it if you use packing cubes to store your clothes. These Gonex compression cubes come with a zipper for the contents and a second zipper to compress the air out of the clothes inside. This way you don't have to worry about carefully rolling your clothes together – just fold them flat, put as much as you can into the bag, and zip it down to compress.


These tips aren't intended for anyone in particular – they're just items and practices that I've found which help me make a good trip great. I hope some of these help you on your future trips, and I'd love to hear what you like to use when you travel.