How to Pack a Carry-on for 2 Weeks

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Trying to pack a carry-on for 2 weeks is no easy feat! It has become my latest obsession, and through trial and error, I’m getting better at it!

One of my most challenging attempts was my 16-day trip to Colombia. Temperatures varied from a low in the low 40s in Bogota to highs in the mid-90s in Cartagena, where it was really humid.

It was not easy packing for two weeks of what I’d need in a carry-on bag, but it was well worth it. You’ll know exactly what I mean once you start!

I did have a few misses—and I’ll share those as well as a packing list that you can adapt for the specifics of your trip. You can absolutely pack for 2 weeks in a carry-on bag, and here’s how!

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1. Choose the Right Carry-on Bag (+ Options!)

Packing for two weeks in a carry-on all starts with getting the right bag. You want to be sure it will fit on most airlines.

  • Check the size—If you’re taking a smaller commuter flight or flying on a discount airline, their size allotment is even smaller. Airlines show their size requirements on their website, and I often use Ryan Air as a guideline as theirs are quite stringent. You can be charged a lot in fees to check a bag if it doesn’t fit.
  • Leverage technology and features—Look for bags with features like compression straps and solid zippers. If you bring just a carry-on, you are going to pack it full!
  • Make sure it’s lightweight—You’ll find great bags that are really light, making it easier to navigate. Save the weight for your belongings instead of the bag.
  • Consider what you’ll do on your trip—You have lots of options for carry-on bags, including wheeled bags, duffels, and backpacks. Will you be walking on cobblestones or uneven terrain? Or will you be mostly on roads in the city? Give this some thought when choosing your bag.

4 Great Carry-on Bag Options

Here are some of the top options for carry-on bags with a range of types and styles. All of these are really good brands, so if you like what you see but it’s not quite right, go to their website and see what else they have.

Eagle Creek

I’ll admit I’m slightly obsessed with Eagle Creek. When I visited Colombia, I brought their Expanse convertible International Carry-on. It’s tiny but I love it because it has straps so it can be worn as a backpack and great compression straps.

They don’t make it anymore (and you can’t have mine!) They do offer this international carry-on, which is great.

I have one of their backpacks and a roller bag as well and love them all. They are incredibly sturdy, have a really thoughtful design, and are durable. Their bags are also light and comfortable, which is important.

Many of their bags also have locks on the zippers, which comes in really handy in certain areas.

pack a carry on for 2 weeks, suitcase, day pack, suitcase at airport

My beloved Eagle Creek convertible bag

Travelpro Luggage Platinum Elite 21” Expandable Carry-on Spinner

Travelpro has an extensive line of carry-on bags so there are a lot of great options. However, this one seems to often bubble to the top. It’s small enough for many international carriers with sizing restrictions and does allow you to expand it if needed.

It includes a lot of thoughtful and very usable features. It is a four-wheel spinner, so it is easy to roll and glides really well, even on cobblestones. And it’s quite durable—important for a bag!

It has some nice features inside, including a wet bag and a garment bag. No worries about wet bathing suits! And it has handy interior pouches for storage and access. There’s also a built-in luggage tag holder.

Buy the Travelpro bag now. It comes in red, black, and grey.

Away Carry On

Here’s a brand that has gotten a lot of hype in recent years, and for good reason! They have raving fans due to the quality, durability, and thoughtful design of their bags. If you prefer a hard-sided carry-on bag, the Away Carry-On is a great option.

It’s a great size to fit on most flights. It also has an interior compression system, which is helpful in maximizing space, and a water-resistant laundry bag.

An interior compression system and water-resistant laundry bag make it easy to pack all of your essentials. It also has a 360° spinner for easy use.

The secret weapon in this bag is for travelers who want to stay connected while on the go—there’s an ejectable USB charger you can use to charge your phone up to four times! Wow. For someone who always forgets her external battery charger, this is an amazing feature. (You can easily eject it should you need to go through security).

If you want a roomier carry-on bag, check out this Bigger Carry-On. You can’t take it on some of the smaller international flights, but it will fit on most major airlines.

Osprey Ozone

Those who are familiar with quality backpacks will recognize the name Osprey. In fact, my larger backpack is an Osprey, and I love it! Osprey makes a lot of great packs.

The Osprey Ozone includes both interior and exterior compression straps to enable you to pack it as fully as possible. There is an easily accessible compartment at the top of the bag. You can use it to stow liquids, making it easy to pull them out at the airport.

There’s a strap on the front of the bag so that you can attach a smaller bag to it. And there is a rear zippered pocket for carrying a laptop or a tablet. It also has a carrying handle that can be used when you can’t roll it easily, like on cobblestones or uneven ground.

2. Select the Right Personal Item Bag

Bringing a good personal item bag is just as important as your suitcase. You’ll want to consider what you’ll need it for during your trip, as this bag often serves as a day bag when you’re traveling.

Do you need a backpack for hiking? Or do you want a tote for walking around the city? Just like with your carry-on bag, you have lots of options for your personal item bag.

Make sure it has a zipper close so you don’t lose things. Having compartments to separate things and easy access to what you need on the flight on the outside is really helpful.

You May Also Like 7 Best Personal Item Bags for Flying

3. Wear Your Bulky Clothing

This one can make a big difference in the room you have for packing. If you’re packing jeans, consider wearing them on the plane to take up less room in your bag.

If you’re hiking, wear your boots on the flight. This leaves more room in your bag, making it easier to pack for 2 weeks in a carry-on.

Wrap your sweater or sweatshirt around your waist and keep your jacket out of your bag. These items tend to be more bulky and take up more room, which could go to important things that you need to bring.

4. Pack Clothing that Wears Well Together

If you’re going to pack a carry-on for 2 weeks, you need to make sure you have options with what clothing you bring.

Bring some neutral items and some prints that match so you can wear different items together. Also, consider tech fabrics or lightweight wool that wears well. You might be able to wash a little less, depending on what you bring.

I love wool and have been really enjoying my Unbound Merino clothing. It’s soft and not scratchy like wool clothing used to be. And it wears really well! It’s not cheap, but it’s well worth it!

5. Layer, Layer, Layer

The best way to travel for a longer period of time, especially when you have significant weather variance, is to bring layers.

When I took my 16-day trip to Colombia, I packed clothes for the hot weather in Cartagena. I used those same pieces to wear as a layer under my warmer clothing. This way, you can be flexible and have options during your trip.

6. Use Compression Packing Cubes

Do compression packing cubes really make a difference? YES! They most certainly do.

Not only do packing cubes help you organize your bag, and they help you unpack easily as well, but they also help you fit more. Compression packing cubes are even better.

I love my Eagle Creek compression packing cubes. They pack down well, and the zipper really holds up!

packing for 2 weeks

7. Do Laundry

You may be on vacation, but doing laundry during your trip can really decrease the amount of clothing you need.

If you rent an apartment, there may be a washer in the unit or in the building. If you stay at a hotel, some will launder your clothing for you for a charge. You might also find a laundromat close by. What better way to feel like a local!?

You can buy laundry detergent or even bring a small packet that you’ll find at the store. The washer sheets work really well now, too, and they’re easy and small to pack.

You can also do some sink washing, depending on the item. Clothing like underwear and tech fabrics wash easily in the sink.

How to Pack a Carry-on for 2 Weeks: Carry-on Packing List

Below, I have detailed what I brought to Colombia. If you’d like a printable packing list template to adapt to your needs, I’ve got you covered! It includes all you need to pack a carry-on in two weeks.

Clothing to Pack

  • Jeans—I’m a fan of boot-cut jeans and tend to go with Eddie Bauer jeans. They have a lot of styles to choose from, they’re comfortable and wear well.
  • Black knit pants
  • Hiking pants (that convert to capris)—I love these Prana Halle Roll-up Pants. They have a number of different styles, but they all are pants that roll up to capris. They fit well, and I believe that they meet both needs. You can hike in these and go out as well. I also like these roll-up pants by Kuhl.
  • Capri pants (that convert to shorts)—These Kuhl shorts or these are my go-to’s.
  • Long knit dress (converts to a skirt)
  • Four t-shirts
  • Fleece shirt
  • Long-sleeved thin wrap—This Eddie Bauer Daisy Wrap goes with me everywhere!
  • Long-sleeved shirt
  • Thin down jacket—Patagonia down jackets are comfortable and last forever. REI makes great ones as well at a lower price point.
  • Fleece jacket—This Columbia fleece is what I use. They are affordable and have everything you need.
  • Raincoat—This North Face Venture 2 raincoat is my go-to. It’s comfortable, has lots of pockets, and it’s breathable.
  • Hiking sneakers— I love these Teva shoes as they are great for hiking and walking around a city in comfort.
  • Merell sandals/flip flops—I have always loved Merell, but lately, I have been wearing my Chaco Spot Flip Flops everywhere. They went with me to Colombia, and I always wear them. They are rugged and last and are so comfortable and supportive.
  • Close-toed shoes—These black flats by Olio pack down small and are quite comfy.
  • Two pairs of socks and one pair of compression socks
  • Three bras and seven pairs of underwear

Other Packing Items

  • Laptop
  • Ipad
  • Phone
  • USB cord
  • External phone battery
  • External hard drive
  • Two collapsible water bottles (one with a filter)
  • Day bag-I LOVE my Travelon bag (shown below). It has lots of compartments, with theft protection, including locks and RFID blocking.
  • Travel journal and pen
  • Toiletries (toothbrush, toothpaste, conditioner, soap, deodorant, hair gel, bug cream, sunscreen, face soap, face cream, face powder, cover-up, eyeliner and chapstick, medicines, tongue scraper)
  • Umbrella
  • 2 compression packs
  • Glasses and glass case
  • Magnifying photo lens for iPhone
  • Medications
carry on bag

Note: generally, trips require a power adapter and sometimes a converter as well. On this trip, I didn’t need to bring them.

I had a few small odds and ends tucked in, including almonds for snacks, some United States cash (in case my ATM card didn’t work for some reason and I needed access to money), and a few other small items, but this was it. And I got it all in my two bags!

How to Update the Packing List

This packing list is an example from one of my trips. It included what is essentially three seasons, as it was very hot and humid in Cartagena, very cold in Bogota, and in between everywhere else. That makes it so much tougher to pack for a trip when the weather varies so greatly!

This can be adapted to the details of your trip. If you go to a place that is hot the entire time, of course, you won’t need to pack sweaters, sweatshirts, and a heavy jacket. You may want to add a bathing suit and a quick-dry towel or a sarong, and more tees, shorts, and skirts.

It’s a good idea to pack at least a light wrap or jacket, as nights can still get cold, even in the tropics or areas with warmer weather. And of course, if you go to restaurants or stay at a hotel, it may be air-conditioned.

If you stay in a cold-weather place, packing can be more challenging as warmer clothes tend to be bulkier. In this case, consider layers.

If you’re trying to go light, bring just 2-3 sweaters and sweatshirts and add many layers, including tanks, tees, and thermals.

They can keep you warm or even warmer than a thick sweater. Doing this also helps as you can swap out the layers for laundering more efficiently and run less risk of shrinking them!

packing, suitcase, woman rolling suitcase in the airport

My Misses and Packing Improvements

There were a few areas where I could improve my micro-packing skills to pack a carry-on for two weeks better. In the spirit of sharing and lifelong learning, I’d like to share:

Packing Misses

  1. Bring earplugs. Man, oh man, did I regret not having these in Bogota. I loved my hotel, but it was open-air and on a very busy pedestrian street with many clubs belting loud music.
  2. Test things: first, I brought the clip-on sunglass case for my glasses but never checked that my sunglass clip-ons were in it! Novice mistake. Second, I got a new external battery charger for my phone and didn’t test it first. It didn’t work, and that made things challenging because as much as I love taking pictures, I use my phone for navigation as I have absolutely no sense of direction.
  3. I didn’t bring a bathing suit. I learned that there were hot springs in Manizales that were highly recommended, but I wasn’t prepared. Even though I figured I could buy anything I needed that I didn’t have, who wants to go bathing suit shopping while on vacation? Not this girl.

Packing Improvements

  1. Consider not bringing my laptop. I would prefer to do research on my laptop than on a phone, and had big ideas about working on my blog while I was traveling. The reality was that I didn’t do any writing. And, while my computer is more convenient for responding to emails, etc. I am not sure it was worth the space and weight.
  2. Bring a micro hairdryer. I have a tiny one that I got years ago from Brookstone. I had checked that all of the places I stayed at had hairdryers, and yet one of them did not.
  3. Don’t bring a raincoat and an umbrella. I had figured the umbrella was easier to stash in my bag, but the jacket was more practical. However, having both took up space and added weight. I only used the raincoat once, and I never used the umbrella. I recommend choosing one or the other, and the jacket makes more sense.
packing a carry on for 2 weeks, suitcase, backpack, daypack, packing, bags in the airport

Reasons to Carry On Only

When I think of my first international trip to London, I can’t help but laugh. I packed the largest roller bag I could find and a very large shoulder bag for clothes that I could barely lift. Can you imagine?

My, how things have changed, and I now find it a fun challenge to reduce what I pack as much as possible. Of all of my tips for traveling better, reducing what you bring is really one of my favorites.

I prefer to carry on and haven’t intentionally checked a bag in quite a few years.

Some smaller planes require that you check any bags that do not fit under the seat. Or, sometimes, you may have to check a bag due to policy or because they don’t have overhead space.

Benefits of Not Checking a Bag

There are a number of great reasons not to check a bag when you fly.

  • You can’t lose your bag if you keep it on you. No more arriving at your destination and learning your bag is missing. And you don’t need to worry about stolen items when your bag is in your possession.
  • No baggage fees! More money goes to your travels.
  • No waiting. What’s worse than getting to your destination and waiting and waiting for your bag to arrive? Simply de-plane and go!
  • You have everything you need for your flight. It’s a good idea to keep what you need in your personal item bag. But sometimes we forget, right? If it’s important enough and you have your carry-on bag with you, you can dig it out.

The only real downside of not checking a bag is that you do need to carry it through the airport. It’s usually not a big deal unless you have a really tight connection. Then, consider it a workout!

Ready to Pack a Carry-on for 2 Weeks?

Packing is an important part of any trip. Pack too much, and you’re weighed down, and pack too little, and you’re buying a lot of what you need. It’s important to plan in advance and to do a dry run to ensure you’re able to pack what you most need.

Though I generally pack a day or so before trips, I did a bit more planning for this trip to Colombia.

The great thing I learned is that I could have stayed much longer on a trip with what I brought. I would have to do laundry again. Depending on where I would go, I might need a couple of other things, but overall, this packing would work.

As I mentioned, it has become a game of sorts to me, a challenge to pack as minimally as possible for trips. Yes, I like a challenge!

I did have to check my teeny-tiny bag on the in-country flights. However, I didn’t pay any fees to do so. Also, I never had issues with the weight of my bag because it’s pretty challenging to load it up too much when there is so little space! I did manage to bring some small gifts home, so overall, my packing was a success! You can do it too.

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  1. Thu Rogers says:

    Great tips! I also roll my clothes. I have never used the cubes, instead I use those plastic compression bags. I like to have 2 so I can separate clean from dirty clothes while on the trip and/or packing to return home.

    1. What a great idea about having the two bags! Thank you for sharing that. I do have some of those plastic compression bags as well so I’ll give that a try.

    2. Camille G says:

      Great article. Friend and I are hoping to go to Japan *if travel restrictions by April 2022* by way of Central Florida, Southern California and Hawaii. She has limited mobility so I’m with you when it comes to carry-on luggage especially if I’m toting and carrying most of the luggage.

      1. Thank you! It definitely takes some thought but if you plan to do some laundry, bring clothes in great tech materials, and are dedicated, you can do it! Sounds like an amazing trip! I hope you can go.

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