I think a lot about how to pack a carry-on — and indeed, how to dress — on the plane: Planning well can be the difference between a mini-retreat, with entertainment and snacks, and a freezing-cold brain prison. Below, you’ll find everything I bring to keep it more in the former vibe than the latter.

I will add here that of course you want all your essentials in your carry-on, rather than any checked bags: medication, wallet, etc. etc. One thing I often pack by accident into my checked bag is charging equipment: cords and battery packs and wall chargers. Of everything here, the thing I forget most often is cables: a USB cord to charge my phone, a full laptop charger, and a cable to connect my headphones to the plane’s entertainment system.

A quick note about budgeting, as several of the items below are expensive. As a freelance travel writer, my income varies hugely from year to year: It stabilizes when I take a staff job, and then occasionally craters when I’m freelancing, including some years when my income fell under the poverty line. (Freelancing is not for the faint of heart.) While I’m fully employed, I try to buy quality gear that will last through the rough periods — during my last staff job, I bought the Away bag and both pairs of headphones below, and I’m hoping I’ll have them for years. I’ve had the same Gregory backpack since 2012, I only replace my phones when they’re lost or destroyed, etc. And I’ll add that I’m happy to travel with well-used gear — it’s less of a target for thieves.

Affiliate links below. 

Gear

1. A 30-Liter Gregory Backpack

I much prefer to travel with a backpack versus a suitcase. You have total mobility, whenever you want it: Stairs? Elevators? Who cares!

The size is important. I wanted a 30-liter pack — I just looked and that size is rated for 1-3 day(!) trips. (I routinely use mine for month-plus-long stays.) The fastest way to make a trip miserable is to overpack, and it’s virtually impossible when your bag is this small. Another huge bonus is that it can fit under an airplane seat, which means you’ll never have to check a bag — or, even better, worry about overhead space.

The model I have — an older version of the Gregory Z-30 — is no longer available, so I’m suggesting the next size up: the 45-liter Facet. Gregory has other 30-liter bags, but now they’re structured more like daypacks — I like having more side pockets, and lighter materials, of this slightly larger size.

2. For Nice Trips, An Away Carry-On

Sometimes, when I’m not traveling solo (or I’m writing about a hotel where it will matter if I show up looking like a ragamuffin), I’ll bring this nice Away carry-on. It’s fine. I suggest waiting for one of their limited-edition colorways — I loved their no-longer-available Aura collection.

3. In an Era of $5 Diet Cokes

Empty on the way through security, then filled with water before the flight. Obviously there are a thousand different models and color combos, but I love this “Hawks in Flight” version from Bird Collective.

Electronics

4. A Google Pixel

I’ve weirdly been in the Android phone world since I gave up my iPhone 3 for a gifted Samsung Galaxy a million years ago. I’ve loved my Pixel, though recently I’ve felt like I’m seeing nicer photos on my sister’s iPhone. But I’m one of those people who won’t give up their phone until it’s lost or destroyed, so I’ll be getting by with my Pixel 7 for a while.

The best thing about Pixels is that they’re made for Google Fi service (note you can use an iPhone, or any other phone, on Fi as well). Its international service can’t be beat: “unlimited” international data — though they’ll throttle you at a certain point, and it’s a violation of the terms of service to use it only overseas (a dilemma if you’re traveling with it as a digital nomad), though I don’t know how much this is enforced. Calls to the U.S. from overseas vary by country; from France, they’re 10 cents a minute, though it’s pretty rare I pay that since wifi calling is free, and texting both ways is free.

5. Macbook Air

I cannot believe anyone here is going to base their laptop choice on my rec, but I will say that after my Macbook Pro was stolen (out of my apartment, by a thief who came in through an open fifth-floor window), I downgraded to a new Air and didn’t notice a difference, even though I’m doing moderately heavy lifting (video editing, etc.) Go, Air! Don’t forget about educational discounts if you qualify, and refurbished models if you’re looking to save.

6. Bose 700 Noise Cancelling Headphones

There’s no better way to reduce airplane noise (which is considerable!) and isolate during a long flight than with these headphones. After too many hours using a sander with no ear protection (don’t get me started), I can barely hear my phone or laptop on a plane without jacking up the volume. These headphones mean I can tune everything out for up to about 18(!) hours.

I’m obsessed with these Bose headphones and once rescheduled to a later flight when I realized I’d left them at home. I have an older version of these, the 700s. These have 11 levels of noise cancellation and free two-day shipping from Bose. One thing I’ll say is that after two years I’m noticing some wear in the “protein leather” (a pleather, but very soft) covers, which has me slightly concerned. I do use them constantly — not just for flights but at the gym, on walks with the dog, etc.

7. Google Pixel Buds Pro

I feel like a princess when I do this, but I always switch from the Bose headphones to earbuds when we land — it’s too easy to lose all sense of spatial awareness in the larger ones. These, from Google, have great noise cancellation while not limiting my understanding of where I am in space. (Read: I’m less likely to walk into things wearing these.)

8. The Best, Heaviest Coat I Can Afford

I feel like many of these picks somehow involve not being cold. There’s nothing worse than getting somewhere and realizing you don’t have proper protection from the cold, because you’re not going to want to buy an emergency new coat, and it sucks, gutting it out when you have a chill. You don’t want to do anything but stay inside, wrapped in a blanket.

Of course, since you’ll be on the move, you want to optimize for both cold protection and packability/weight. This Fjallraven coat is filled with down and warm enough that I can wear it in the middle of winter in Iowa with just a T-shirt underneath (handy for going to the gym). I have a heavier wool coat from Sandro, but it’s super bulky, and not good for travel. In fact, I’m wearing this Fjallraven right now, on a plane, and I am extremely warm, and I could not be happier.

Clothing

9. Walkable But Not Too Sporty Sneakers

What I want is something between my Nike Metcons (my choice of gym shoe, I love them) and Vejas, which are very stylish but which I also don’t trust to be comfortable on 10,000-step days. The best answer is colorful and vintage-styled Nike Daybreaks — they’ve been discontinued for the moment, but they’re available everywhere but Nike.com — like the ones shown above, which are on sale at ASOS.

10. American Vintage Cashmere Sweater

Just something warm and blanket-like for when the air conditioning is on too high — I have this one from American Vintage.

11. Topshop Jamie Jeans

They’re not what they used to be, before Topshop was sold to ASOS, but I still love the Jamies, especially for traveling: They’re high-waisted and slim, and the fabric is stretchy enough that it’s comfortable on the plane. I used to prefer leggings but just got tired of looking like a pile of laundry in the airport. Respect if you can pull it off, but I couldn’t.

These go on sale all the time, so just keep an eye out for your preferred color and/or embellishment.

Entertainment

When I’m on top of it, I have a very strict regimen for my on-board entertainment. Otherwise, I just stare out the window.

11. Downloaded Comedy Specials

I take a lot of short flights — mostly between Cedar Rapids and Chicago — so I prefer entertainment that I can dip in and out of without ruining something more in-depth. Comedy specials are perfect for this — this year, my favorites included Beth Stelling’s If You Didn’t Want Me Then, Mo’Nique’s My Name Is Mo’Nique, John Mulaney’s Baby J, and Sam Jay’s Salute Me or Shoot Me.

12. Downloaded TV

So comedy is Tier 1. If I have a longer flight, I want something I can dig into, which is where actual television comes in. This year, my favorite shows were: Beef on Netflix (obsessed — Rolling Stone called it “this oddest, darkest of dramedies,” which I co-sign), Barry on Max (weirdly, that same description applies), Succession on Max, and a zillion more. All are downloadable (the Max shows depending on your membership level — it’s only with the no-ads service.)

13. Downloaded Audiobooks

I save this for the longest of flights (and road trips, of which I am a master, having done the 1000-mile trip between New Jersey and Iowa about a dozen times by now). The right audiobook can make the difference between a smooth and successful trip and a slog — and the right audiobook, I’d argue, can make the perfect book even better. I actually did a little post on this a couple years ago and I really did get to some of the best: The Handmaid’s Tale (read by Claire Danes), Trevor Noah’s Born a Crime, and Virginia Woolf’s To the Lighthouse, which is read by Nicole Kidman and absolute perfection. To that list, I’d add World War Z: The Complete Edition: An Oral History of the Zombie War, which includes voice actors like Martin Scorsese, Mark Hamill, Alan Alda, and the author, Max Brooks, as well as Gary Chapman’s The Five Love Languages. 

14. Actual Books

The best books for long flights are big, epic books with lots of intense world-building. My favorites in this category include: Pachinko, obviously the entire Game of Thrones series, the His Dark Materials trilogy, Outlander, The Stand, and a million more.

Miscellaneous

15. United Club Infinite Card

I have more credit card debt than I should, and I don’t recommend that anyone irresponsible (like me) take out additional credit if they can avoid it — it’s too easy to overspend. That said: I love this credit card. It has a high annual fee ($525), but the perks may very well make up for it. United lounge access is free, as are up to two checked bags. If you’re flying on someone else’s dime, or if you have elite status, that might not be so exciting, but it is for me. Even outside of just “lounge access” (not a necessary thing!), I save so much money eating (for free) in the lounge that it makes up for the cost. Eating in the lounge also means I’m less likely to get by with sugary snacks or fast food — it’s a total win. Here’s a link — it’s the one on the right.

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