How to Pack for Alaska in a Carry On

Laura Lopuch

I looked down at my usual carry on bag — an open top duffel — and back to Frontier Airlines’ personal item dimensions.

The duffel was too big by several inches. If I took it, I’d be forced to pay $25 as a carry on fee. That seemed silly: paying to bring unneeded things on a trip, when I could save that money by simply bringing less.

The following night, my husband and I were booked on an 8:30 pm flight to Anchorage. Tickets had been redeemed with miles, saving us over $900.There I was wrestling with bags to save us a total of $50 in carry on fees, thanks to Frontier’s latest price ranking strategy to charge for carry ons, checked bags, seat selection, and pre-boarding.

But their weak spot was that one personal item per passenger was still free. And that’s exactly where I was aiming. My personal item would be my carry on.

My trusty Timbuk2 messenger bag (a.k.a. my weekender bag) would comply with the personal item size requirements. Yet I’d never packed for a five-plus day trip to a destination with notoriously fickle weather — like Alaska in the fall — in that bag before.

If I was packing for this trip now, I’d pack in either the Outbreaker daypack, with the nicely sized computer sleeve and exerior pockets to add just a little more flexibility, or the packable duffle, organized inside with the packing cubes. Of course, if I was willing to pay for that carry on, then the Outbreaker 35 would have felt as spacious as a steamer trunk!

I wondered if I could really pack for five-plus days and plan for unpredictable weather in a smaller-than-normal carry on bag.

Challenge accepted.

Core Packing List

First, I had to figure out what my core items to pack were. In other words, what types of items I’d need for the trip. From there, I could figure out where to trim the fat from my list.

After checking out the weather forecast (50-60s F, sunny and potentially overcast, cool nights) and aiming for layer-friendly clothes to max my options, this is what I came up with:

  • Two short sleeve shirts in hopes of a warm day
  • One long-sleeve cotton cardigan
  • Two three-quarter length shirts
  • One tank top
  • Four pairs of underwear
  • Five pairs of socks, including one workout pair
  • Running shoes (to wear — I planned on jogging a few miles there)
  • One workout shirt
  • Running pants
  • One lightweight, wind-resistant and waterproof jacket: FlyLow Gear’s Vixen
  • Scarf
  • Book I was reading
  • Backup book to read

I dove into my closet, pulled the clothes out, rolled them up, packed my bag and realized this was going to be harder than I thought. My inner play-it-safe voice yelled that I must have two short sleeve and three-quarter length shirts, but there wasn’t enough room. Even if I wore one entire outfit on the plane (jeans, shirt, scarf, jacket), my bag was still busting at the seams.

What if I wanted to bring anything home from Alaska? Where would I cram it?

My husband eyed the bag and plucked out the backup book, “Really? You’re not going to read this there.”

I needed that book. What if I ran out of reading material?

“Alaska has bookstores if you finish this one, you’ll be fine.” He picked up the book I was reading, “See, you’re not even at page 50 and this has, what, 450 pages?”

He was right. I emptied my bag, silenced my inner freaking out voice, and went to work again.

Narrowing it Down

This time when I felt the tug of indecision about taking an item, I laid it aside. I told myself sternly that this trip would be amazing, whether or not I brought three shirts and that, if I needed something, it would a five-minute trip to the store.

It was a challenge to discard the extra shirts. Leaving them made me feel anxious and uncomfortable.

I told myself to live a little dangerously and not care if someone noticed I was wearing the same shirt from two days ago. I told myself to take a deep breath, think about how light and free I’d feel with fewer items on my back, and how excited I was to see glaciers. What I brought wouldn’t make or break my trip.

Alaska Packing List

In the end, this is what I packed for Alaska for five-plus days, in a smaller-than carry on bag:

  • One pair of jeans (wore)
  • FlyLow Gear Vixen all-weather jacket with a hood (wore)
  • Short sleeve light fabric t-shirt from target (wore)
  • Target long sleeve cardigan (wore)
  • 3/4 sleeve button-down shirt
  • Short sleeve shirt
  • Blue infinity scarf (tied to outside of my bag)
  • Workout shirt
  • Sports bra
  • Workout shorts
  • Running shoes (wore)
  • 4 pairs of underwear and socks
  • One book
  • Moop paperback handbag (tucked inside messenger bag for flight)
  • Alarm clock
  • Reading light
  • iPhone power cord

Alaska was staggeringly gorgeous. The trip went off without a hitch. It was overcast for the majority of our trip, but one glorious day the sun broke open the sky. It felt like summer. Even the whales cooperated, blessing Homer Bay with flukes and water spouts.

It was, however, colder than I anticipated. The sun up north is weaker than what I’m used to in super-sunny Denver. While I wasn’t cold enough to warrant buying anything, when I go back, I’ll make sure my bag has long sleeve shirts and warmer sweaters. No short sleeve shirts for me. That breeze off the glaciers packs a punch, sneaking into your warm spots in a devilish fashion.

I didn’t miss the things I didn’t pack. My bag was lighter, both physically and metaphorically without that extra baggage. And, I had room to bring home a coffee canister, even if it was filled with my dirty shirts.


You can still pack in a carry on (or smaller bag, like a personal item) for a 5+ day trip to a destination with fickle weather, like Alaska in the fall. Pack what you’d normally pack, then weed out the multiples so you end up with one or two similar items (like shirts).

Aim for layer-friendly clothes to be prepared for any type of weather. Don’t forget a lightweight, waterproof and wind-resistant jacket (preferably with a hood) to fend off chilly winds.


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