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Alaska Packing List: How to Pack for 5+ Days in a Carry On

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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.

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.

TL;DR

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.

Image: paxson_woelber (Flickr)

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  • Hi Laura, Planning for highly variable weather is challenging. Here are some things to consider next time.
    The key is multi-purpose clothing – items that work well in hot OR cold weather. Technical clothing performs best as it looks like street clothing but can handle workouts/weather. Your big mistake in your list is that you separated workout gear from regular clothing. Great travel clothing should be able to do **both**. This is the key to packing light in a small bag.
    Think about bringing a shirt that has roll up sleeves. Rolled down for cold, rolled up for glorious days.
    Think about bringing a light weight long sleeve or 3/4 sleeve shirt for layering or alone. Wear it like a sweater over other shirts when it gets cold.
    Bring 1 sweater (preferably merino) for layering. A cardigan buttoned up with a nice necklace is slinky enough for dinner. Layered over other clothing it is warm (even when wet) making it good for variable weather.
    Bring 1-2 light weight short sleeve technical tees that you can layer UNDER other layers as needed. Wear them alone on glorious days. You can work out in technical tees because they wash and dry quickly. Take a peek at the Royal Robbins Noe tees.
    Think about bringing lightweight base layers. I prefer a 3/4 sleeve filament weight silk long underwear top and a pair of light weight leggings that I can wear under pants. The leggings may also be used for workouts and for sleeping.
    Jeans are too limited for ultra-light travel. They don’t work in a storm. You can’t wash them easily. Think about bringing convertible travel pants. Not the kind with zip off leggings (yuck!) but the kind that roll up into capris. These dry faster than jeans if they get wet. The Royal Robbins pencil pants are cute, and their adventure discover pants aren’t bad either.
    On shorts – I think that they are over rated for travel. I’m a fan of skorts, especially Title Nine skorts (AKA skirts with benefits). These are made of technical fabric and dry quickly. Wear them with leggings if it gets cold. Wear them out with a cute top for dinner out.
    Dump the alarm clock and use the alarm function on your iPhone.

    • Hi LadyLight, thanks for your extensive comment and suggestions. While technical or workout clothing is great for long trips of 3+ months where you’ll be washing your clothes, for trips shorter than two weeks, I prefer my normal clothes since I don’t wear workout clothing as my regular clothing. I like to feel like myself and be comfortable. For me, that means jeans, cardigans, and mining my normal wardrobe for clothes.

      Everyone has their own unique style and methods on what works for them! Isn’t that the great part about travel? Over time you develop what works well for you and how you like to travel. Sounds like you’ve discovered your style, which is awesome!

      • Hi Laura. I understand that you of course want to use “regular” clothing. I think the jeans are a problem though. If it had rained (especially hard) you would have been soaked and in trouble. Hence the recommendation for synthetic pants. This normally isn’t an issue for city trips but becomes critical for outdoors trips.
        I think you also misunderstood my comment on workout clothing. Prior to the 90’s specialized workout clothing didn’t exist – people trained in regular clothing and it worked OK. That’s my point – just work out in normal clothes and leave the workout gear at home. That saves space or leaves room for a few more tops. The recommendation for technical tops is because your trip is an outdoors trip. If you had been in a cold rain your cotton tops would become dangerous. Hypothermia kills.

        • @LauraLopuch:disqus @LadyLighttravel:disqus In the future, we should do a point/counterpoint-style post showing how to pack for the same trip with (1) technical/performance/multipurpose clothing and (2) normal, everyday clothing. Aside from the specific items, we can outline the pros/cons of each approach and how you might mix them. I’ll talk to Jenn about this.

          • @FredPerrotta:disqus @LauraLopuch:disqus Oooh, fun! Especially if we have the “why” behind the choices. That gives people enough info to make their own choices for their own style of trip based on their own circumstance.

        • @LadyLight, thanks for the recommendations on technical tops and synthetic pants. You’re right – wet clothing can be dangerous in cold weather.

          @FredPerrotta, great idea! I’m game.

    • TheWhitePhantom

      LadyLight, I think you are confused on what a comments section is. It is for comments on the post, not a place for you to waste my computer screen space with a post of your own.

      Laura,
      I really enjoyed your post. Frontier has indeed made a new challenge for those of us that refuse to check luggage or pay seperate fees. Your post had good information on how to pack normal clothes people should wear in public. Not clothes that make you look like a walking REI ad.

      • @TheWhitePhantom – I think I’ll let the Tortuga folks decide on what the comments are for. They’re paying for the website after all. If Fred wants me to stop commenting then I shall certainly do so! I also believe that I commented on the post – I disagreed with some of the info. Last time I looked it was allowed if done in a respectful manner.
        As an FYI, if you actually look at the clothing I recommended it looks normal and not like jungle clothes. I personally wear them when I’m not traveling because they are comfortable, cute, and stylish. The whole point of great travel clothes is that they look…. normal. I have integrated them into my personal wardrobe and I use BOTH types of clothing when I carry on. This is not an either or proposition.
        I have personally traveled with a single under seat item on several occasions, including a wedding. I never looked like I stepped out of an REI ad.

        • Your comments are fine by me, though everyone will have their own style. That’s why we brought on more writers like @LauraLopuch:disqus to showcase a wider variety of travel and packing styles.

          I tend to mix everyday clothes, like Laura, with a few technical pieces like socks, underwear, and my new Outlier “jeans.”

          My hope is that readers can find writers that they identify with and follow them for the most tailored recommendations. I also like to challenge people’s assumptions with more extreme packing posts so that everyone can see what’s possible, even if it isn’t for them.

      • @TheWhitePhantom, Thanks for your comment! Glad you found the post useful. Agreed; Frontier has upped the challenge on packing light and in a carry on only. Game on! 🙂

      • Thanks for commenting. We like to have an open dialogue with other travelers and writers, so we welcome @LadyLighttravel:disqus’s comments. If you aren’t interested, that’s totally understandable. Just skip right by. We hope that readers can writers with a similar style so that they can find the best advice FOR THEM. If you ever think we’re missing anything, let us know with a comment or email.

        • TheWhitePhantom

          I agree that an open dialogue is great to have in posts like this. What LadyLight attempted to do was highjack the post .

          As you mentioned you have many different contributers to account for many preferences. This allows us readers to follow the writers we identify with. It would be great if LadyLight could show some restraint in her excessive “comment” and allow us readers to enjoy a post without having to make the choice of “skipping by” an unnecessarily long and self-promoting comment.

          Again, I enjoyed your post Laura and I look forward to the next one because i relate with your style.

          • @TheWhitePhantom – Stating that I’m trying to hijack a post is a very strong accusation. Perhaps you could clarify why you are accusing me of this? And using the term “self-promoting”? From here it looks like you are attempting to bully /manipulate / intimidate another reader into silence. If this is not your intent could you clarify?

            I took issue with some of Laura’s clothing choices. I did so for a very specific reason – Alaska outdoors is an unforgiving environment and hypothermia is a real issue. Proper clothing for the outdoors is a critical part of hypothermia prevention. Laura got lucky and had pretty good weather. If the weather had turned she would have been miserable at best in her cotton-based jeans and top. The good news is that there are travel clothing choices out there that are outdoors appropriate and look good.
            As to the “why” of this? Maybe I’ve seen too many friends die because of someone making inappropriate choices in the outdoors. I don’t believe it is inappropriate to suggest clothing that looks good AND protects you.

  • Diane

    Just a couple of thoughts on lightening the load, Laura. You mentioned an alarm clock & an iPhone cord. Your iPhone has many alarm options. I use it at home instead of an alarm clock & it works great for travel, to eliminate 1 item.

    Since you like to read, you can download a free Kindle app on the iPhone & get books from Amazon. The phone screen is too small for me to read, so I was traveling with a cheap Kindle. I now travel with an iPad mini & use the Kindle app.

    • @Diane, thanks for the tips! I have considered getting a Kindle or iPad to indulge my reading obsession. However, I can’t quite seem to kick my love of feeling physical books in my hands while I read. 🙂 Sounds like you’ve found a great way of bringing multiple books on a trip without sacrificing space!

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