Pack Light! How To Pack for a 2 Week Vacation With One Carry on Bag

Over the years my peers have asked me “how do you manage to fit everything you need for a 2 week trip in one bag?” And it wasn’t until our last trip to Australia, when a woman asked me “did you really fit all your things in that bag”, that I realized it was something I probably need to share with people.  So here it goes, a step by step guide on how to pack 2 weeks worth of stuff in a carry on bag.

  1. Its all about the bag.  Last year, I decided that we should get quality bags for upcoming trips.  We decided on the Osprey bag and REI bag for 2 reasons.
    • Functionality
    • Size

Both bags have great storage areas, they come with an additional day bag (that we usually use as our second carry on), and the whole thing can be worn as a backpack.

I usually use the REI bag. I prefer the REI because when we are going through check in sometimes they take a second look at the Osprey bag, inferring it might be too large as a carry on.  As you can see from the picture below the Osprey is a bit wider when its full.


  1. Compression bags and pack it cubes are my new best friends! For a 2 week trip these are a must! Especially if you are going to be staying in more than one place.
  • Compression bags are like vaccum bags, but for your clothes! They allow you to fit more clothes while saving space.  Just put your clothes in a compression bag and roll.  The rolling sucks the air out of the bag and Viols! A pile a clothes, cut in half.
  • Pack it cubes help me to organize,  I might use it for undergarments, bathing suits, and accessories. If I have multiple parts to the trip, I will split my clothes up into different pack it cubes so that my bag isn’t a mess and I don’t have to repack it every time we go to a new location.


  1. Toiletries, this is where things can get out of hand.  Below, I illustrate what goes into my toiletry bag.
    • Use lots of ziploc bags
    • Buy travel size products or put your products into travel bottles

For my straight hair days:

For my curly hair/ beach days:

Miscellaneous items:


Final Pouch:


  1. Onto my kryptonite… SHOES… this is the one thing I need to work on… Ideally 3 shoes should be enough (one to walk in, one for dress purposes, and a flip flop). But I can never make up my mind and luckily I have small feet so I add a little more.  This time,  I brought 6 pairs of shoes.  I need to do better, but check out below how I packed it.  Shoes always go on the bottom!

Tip: Fill your shoes with items you can roll. You can also do this with the gaps the shoes make in the bottom of the suitcase.

  1. Clothes.  Now you have to be really strategic about this and there are many ways you can do this.  You have to do a lot of soul searching.
  • My method is always to go with my favorite outfits and things that I know I will most likely wear.
  • I try to stay away from throwing in clothes that I’ve never worn as I don’t know if I’ll actually wear it.
  • Also try to bring items you can mix and match.  I like to bring my jeans shirt as a staple because it adds layers in case I get cold and it can completely change the look of an outfit.
  • I also pack by the day.  Below you will see two rows.  The first row is daytime and the second is evening.  I literally think about what I am supposed to be doing each day and pick an outfit accordingly.  In some of the days though there will only be a shirt or just pants because I plan to reuse something from another day.
  • Remember, 9 times out of 10, in the unlikely occasion you forget something or run out of clothes, you can purchase it at your destination!


  1. Miscellaneous Items: Medicine

7. Finally, I put some of these clothes in compression bags and pack it cubes and there you go you have your complete bag! See the end result below ( the orange is the pack it cubes and my toiletry bag is in the middle):


Here is what we walk away with, including our day bag.

FYI: In my day bag, I put a fresh shirt or outfit, my compressible jacket, make up bag, and on plane essentials bag.



Hopefully you find some inspiration in my steps to  packing light and even save a couple of bucks by avoiding a checked bag! If you have any questions or want to leave any feedback, please feel free to do so below!