Packing Tricks and Challenges

In my experience, there are two kinds of travelers: those who want to check a bag, and those who would rather pull their eyelashes out individually than check their luggage. I tend to fall into the latter category. It is usually a point of pride for me to fit all of my crap into a carry on and a personal item.

There are benefits to my approach — it’s less stuff to drag around if you’re going to be moving from place to place, or have to fit your stuff into a rental car or taxi. You don’t have to pay bag checking fees, or worry that your luggage won’t make it to the destination. You don’t have to waste time waiting for all the bags to be unloaded and unceremoniously tossed onto the luggage belt when you’re trying to get home at zero dark thirty.

However, I will concede that it is a pain in the ass to condense your life into 36 inches and one quart-sized bag of liquids. BUT that is why I’ve worked tirelessly over the years to hone my packing skills to maximize my space and still bring everything I need. Here are my top tricks for making it all fit, and at the end are a couple common packing challenges, and how I would address them.


This is not revolutionary. There are 5,000 other blogs and articles out there telling you to do this. But that’s because it works.


I am deeply in love with packing cubes, especially compression cubes. you can fit SO MUCH STUFF in them. I will typically have one packing cube for pants and dresses, one for tops, one for athleisure and PJs, and one for socks and undies, which all fit nicely into my hard shell carry-on. If you’re going to a warmer climate, just use one cube for your nicer clothes and devote one to bathing suits and cover ups. Roll up your socks and put them inside shoes. Same with belts or scarves. Use up any and all open space. You can either leave the cubes in your suitcase or pop them in the drawers at your destination. Once you empty a cube, use it as a laundry bag so your clean stuff doesn’t start to smell.


Again, it seems like common sense, but I have borne witness to too many people trying to pack boots or sneakers or coats. Look. You are not going to have a paparazzi snap in the National Enquirer of you looking dumb wearing boots and sweatpants in the airport. Just do it. Pack some flip flips or soled slippers in your backpack (we’ll get to the backpack momentarily), and trade your shoes for those on the flight. But I swear to god, if you put your bare feet anywhere on the surface of that airplane, you are no longer welcome on this blog.


I love a travel backpack. To me, a rolling, hard shell carry on and a backpack are the optimum luggage cocktail. You should be able to fit everything you need for up to a week, and you won’t feel like you’re hauling a mini Cooper down the street, barehanded. It’s enough space, but it’s not so much space that you bring a ton of extraneous crap.

You can get something specifically marketed for traveling, like the Beis backpack I have and have linked in my Holiday Gifts post, or you can use any old backpack from high school. In today’s world of budget airlines limiting you to only personal items for free, you can’t be wasting that on a cross body bag. Put the cross body IN your backpack. Pull it out when you’re on the plane. No one cares after you board.

Backpacks have a lot of great features for travelers – a multitude of pockets for your treasures. I like to keep my passport/boarding pass in the very front zip pocket while I’m in the airport. It makes it easy to grab and put back as needed. You can snap your neck pillow right to the strap of the backpack, and same with sneakers you couldn’t fit in your bag. And best of all, you have both your hands free for activities!


While I’ve made it clear that I am anti-checked luggage, sometimes it’s unavoidable, and, for me, that usually on the way back from somewhere when I have acquired various tchotchkes that I cannot live without. Pack an extra small bag (even a reusable grocery bag will do if you don’t have a small duffel or overnighter that packs down flat), check your hard shell carry on, and voila! Extra bag becomes your carry on, and you still have your handy, dandy backpack for flight essentials.

Packing Challenge #1 – Packing for Multiple Climates

I faced this challenge most markedly when I was going to Amsterdam and had a 48 hour stopover in Iceland. What does one layer to go tiptoe through the tulips in the Netherlands in May, and then also wear to take in an Icelandic waterfall in the freezing rain? The answer is layers. Many, many layers. Bring leggings to wear underneath jeans. You could wear either on their own in Amsterdam. Bring a large scarf that doubles as a lap blanket for the plane. You already know you’re wearing those hiking boots on the plane. Get a packable down coat – it’s worth the investment and can stay balled up in the bottom of your backpack until you need it. I ended up (and would recommend) buying a warm hat at your destination. The Icelandic wool hat I bought was significantly warmer than any of the knitted pom pom hats I would’ve brought anyway.

Packing Challenge #2 – My Trip is Super Long, but I Don’t Want to Lug a Huge Bag

My friends, I packed for 11 days in China and Thailand in (you guessed it), a carry on and a backpack. But it took some strategizing. The first thing I would recommend is checking on whether your hotel has laundry services, or just bringing a travel detergent and washing some essentials in the sink midway through.

The second thing you should do is plan outfits ahead of time using basic pieces. For example, if you are bringing a pair of jeans or jean shorts, you know you can wear those multiple days with multiple tops. Bring solid colored or neutral items so everything goes with everything else. Bring accessories with a pattern to jazz things up — I love a black dress with sandals and a leopard cross-body. The cross-body also goes with jeans and a green top, or with black leggings and white t-shirt. You get the idea. Don’t bring 11 different outfits. Make 11 outfits out of 5 or 6 key pieces.

The third thing is decanting your toiletries into silicone bottles. Amazon sells kits that come in airport-friendly clear travel bags. Don’t buy all new, travel-sized shampoos, facewash, and body wash. Just bring your own stuff. You can get really fancy with it and label your bottles like I did. Heaven, to me, is a label maker. Also, if you want to save even more space, you can buy solid shampoo, conditioner, and deodorant that won’t need to fit in your quart-sized liquid bag. Be discerning — do you really need hair spray, heat protectant, and mousse or can you just let your hair do it’s thing for a while on your trip? Toss in a travel sized dry shampoo, let go, and let God.

I know these tricks and challenges are just the tip of the proverbial iceberg. Let me know what your other packing questions are!

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