We tend to learn the most important packing lessons the hard way.
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I’ve felt the sting a few times. From banking on being able to find contact lens solution at my destination to forgetting to pack extra-warm socks, those little mishaps can go a long way in tanking our vacation vibes.
To make things more complicated, every person needs to pack according to their specific needs and preferences.
For example, I’m perpetually cold, so I need to be careful about packing extra layers (and those fuzzy socks). I also pack extra cosmetics, which require special leak-free solutions like latex balloons.
Even as a minimalist packer with a set of tried-and-true hacks, I’m still prone to messing up my final packing list.
That’s not a huge deal for a weekend getaway—but for a week-long or two-week-long trip, those little mistakes can have a serious impact on our level of relaxation and joy.
Want to avoid (packing) disaster for your next trip? Use this step-by-step packing guide to nail your carry-on setup for those more trying two-week trips.
No wasted space. No unneeded items.
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How many pairs of X, Y, and Z will I need?
Let me start off by saying this list won’t tell you how many pairs of pants, shirts, and panties to pack.
The goal of this list is to teach you how to think about packing from a holistic perspective. After all, you’ll need more than clothes. Using this advice, you can put together a crack packing list no matter the length of your trip or the size of your luggage.
For the purposes of this article, I’m sticking to a two-week trip with a single carry-on suitcase because that’s a pretty normal average for a traveler like me. Now onto the fun stuff!
Step-by-step packing guide for a two-week trip
Step #1: Research the weather
Just because you booked a trip to a tropical beach doesn’t mean Mother Nature will abide. The same is true in vice versa for skiing trips and Arctic adventures.
Don’t be fooled into thinking that you know what the temperature will be like based on what it should be—research weather forecasts for your actual travel dates.
If it anticipates rain, you need to pack for rain. The same for cold fronts, heat waves, and typhoons. Here’s my first packing guide rule: never pack your carry-on wishfully.
Step #2: After weather, focus on activities at your destination
From hiking to yoga classes to cooking courses, your final packing list should be guided by the weather and your immediate travel plans.
Even if you plan on taking it easy by visiting museums, exploring bars and restaurants, and otherwise soaking up culture, look into the traveler experience at your destination.
For example, Porto, Portugal is one of the most popular European destinations for American travelers—but the city isn’t the most walkable thanks to its unique stone sidewalks. Those cute flats or more formal loafers might not be a good match, even if they’re normally comfortable.
Step #3: Splurge on space for your true necessities
I don’t go anywhere without my little travel pillow. (It’s technically a plushie, but we don’t need to get into that.) I won’t sleep unless I have the pillow, and there’s no point in going on a trip if I’ll be an insomnia-ridden zombie for most of it.
Before you start tossing aside your favorite pieces of clothing, be honest with yourself about what items are absolutely necessary for your trip to be a physical success.
For example, a sleep apnea apparatus should be your prime focus if you need one to sleep. Or if you’re a remote worker like me, maybe that’s a laptop stand that lets you work from anywhere.
Step #4: Don’t forget about your bag
Are you starting to pick up on my (packing) drift? Clothes might be the last thing you think of when packing, and that’s totally fine.
Along with your necessities (from pillows to laptop stands), think about what you’ll use as a day bag—this apparatus will be your war pony as you explore cities, cruise the seas on catamarans, and more.
My partner and I usually split one bag between us (and he packs it into his carry-on, ahem) that we know is the right size and is comfortable.
I recommend going with backpacks because they’re more comfortable for long days spent walking and you can switch them between you and your partner. Baggu is also one of my go-to’s because they’re tiny foldable totes that let you expand your carrying space when in a jam.
Step #5: Pack your most basic and comfortable pieces
Basic? And comfortable? That might not sound like the most attractive packing list for someone who has been planning their getaway for months and months. That’s doubly true if you’re heading to a fashion capital like Hong Kong or Milan.
Still, I recommend refining your wardrobe down to the most basic and comfortable pieces. No, they don’t need to be boring or low-quality. But they do need to be mix-and-matchable so that you can optimize your clothing combinations. And they must be comfortable if you want to look good while also feeling good.
Remember, the farther from home you wander, the less likely you’ll have the energy to put together Carrie Bradshaw-caliber looks every day. (You’ll probably be battling jet lag and constipation.)
Step #6: Choose ONE nice piece—you don’t need any more
I know I just recommended sticking to your most basic and comfortable pieces, but that doesn’t mean you need to look like a ragamuffin.
Keep it casual for those normal travel days, but also pack that one special piece in your carry-on. You’ll wear it more than once on a two-week trip—and, I promise, it’s okay to re-wear things on vacation.
Here’s my logic. First, that nice piece doesn’t need to be a full outfit. It might be a swanky pair of boots or a nice overcoat. (I also pack a tiny vial of my nicest perfume—that’ll church up any outfit.) The goal is to have some flair without using up too much precious carry-on space. Second, it’ll give you the freedom to buy something nicer at your destination, and then show it off for a dinner date or show.
Step #7: Pack three times to eliminate the unneeded items
This is my personal packing guide take for two-week trips: keep at it. The first round of packing will inevitably have some dead weight. You’ll probably take away a few unnecessary items during the second round of packing.
But, as they say, the third time is the charm. That third packing round is usually when I get cut-throat about my final list—and it’s rarely done me wrong.
