How to pack for a 2-week trip in a carry-on

Checking bags is for the birds.

If you’re going on a long trip, the last thing you want is to haul huge amounts of luggage everywhere you go – especially if you travel at the pace I do, packing up and moving on every 2-3 days. And every time you check your bag, you risk losing it, having items stolen, or making it harder for yourself to switch flights or airlines at the last minute if you need to. At the same time, most of my international trips last at least 2 weeks, usually a bit longer (like 17 days). 17 days of clothing in one little carry on? It’s a challenge, but it’s worth the effort. 

Here’s how I do it:

Step 1: Bring way less clothing than you think you'll need. Bring so little it kind of hurts. 

I know. Half the fun of planning a vacation is the Pinterest board full of cute outfit ideas -- it's so easy to go overboard when you first lay everything out around your suitcase. However, it's critical that each piece you bring is working as hard as possible to earn its spot in your suitcase. Anything even remotely in the 'nice to have' category -- it's super cute, but it fits a little tight in the shoulders or you feel slightly insecure about your gut when you wear it or you can't pair it with at least 3 or 4 other things -- is dead weight that should be culled ruthlessly. Stick to what you already feel confident and comfortable in, and leave the rest at home.

- Build your travel wardrobe with neutral colors and basics. Consider black, white, tan, and grey in basic, flattering, and comfortable cuts your building blocks for travel outfits, as they're most versatile and will give you the most combinations of outfit choices. If that absolutely bores you, bring a few colorful tops in solid colors to brighten things up, and a few lightweight scarves for a pop of style or color.

- Few things are more bulky in luggage than shoes, so take 2 pairs at most. Oh, and make them comfortable and well-built for lots of walking. If you don’t normally pair sneakers or athletic shoes with casual outfits, it’s time to give it a try. It rarely matters where you’re going, you’re going to be walking. A lot. It's not unusual for me to log 18,000-25,000 steps on my Fitbit in just one day of traveling. If you're unsure about how comfortable you'll be in a pair by mile 3, leave them at home. Take your cues from the 'athleisure' trend -- find some cute and well-made sneakers and get ready to live in them.

- Pack only 1-2 pairs of pants. Pants can usually be re-worn a few times before they need a wash, so you’ll get more longevity from them than you will shirts. One pair of comfortable stretchy jeans and one pair of nice black pants should do it. If you're going somewhere very hot, lose the jeans and just bring linen pants.

Remember, the old advice is true: lay out everything you think you’ll need and take only half. Be also very conscious of the fact that nothing will ever fit back in the way you originally packed it; this is the ongoing game of luggage Tetris that you’ll never win. You’re going to need room in your luggage for any shopping you might do, too – one more reason to not fill that suitcase to the brim.

The good news is, packing this light gets less painful the more you do it. Trip by trip, you become quite skilled at identifying space-wasting bullshit and banishing it from your suitcase. 

Step 2. Pack your bag very, very strategically.

This part is actually much easier, thanks to a few handy packing tools I use to maximize the available space in my suitcase.

Eagle Creek Pack-It compression sacks. I have no idea how I ever traveled light without these. They look like giant ziplock bags; once your clothing is inside and the bag sealed, you simply roll them to squeeze out the air out at the bottom - no vacuum cleaner required. I aim to get all my main clothing items to fit into one Medium sized compression bag, then undergarments into a Small (the Large is too big to fit into a carry-on sized rollaway suitcase). I used to use packing cubes for my clothing, and while those are still helpful at keeping your contents organized, I'll never go back to using them for clothing. 

Hint: while I have long recommended rolling your clothing, you don't want to do that with compression bags. You'll get the most out of them if you lay everything as flat as possible into the bag.

- Don't fold your hanging toiletry bag - lay it flat. I've experimented for years with how to fit all my toiletries into my suitcase in a way that isn't awkward or bulky. I think I've finally landed on a solution: a simple hanging toiletry bag laid flat across the suitcase. I have something similar to this Baggallini version, and with the bottom zip-on piece removed, it just fits inside the zippered compartment of my suitcase. The fact that it hangs is also a big perk for small bathrooms with little counter space. Another option: packing a few toiletry bags with slim profiles, like these

- Bring a large-ish purse or small backpack on the plane with you, and pack a smaller handbag for your destination. You never want to pack medication or valuables inside of a bag you plan to check. But even when you carry on, there is still a chance that you'll end up having to check at the gate (it's happened to me several times - usually on smaller planes). So, plan ahead by carrying medications - anything hard to replace, really - in your personal item. I stow my makeup bag and my TSA-approved liquids bag inside. Bonus! This means you don't have to try to fit these things in your suitcase. But don't go overboard and tempt fate - your bag should still be small enough to be considered a personal item.

- Wear your bulkiest items when you travel. If I want to bring a pair of boots on a winter trip, I’ll be sure to plan my outfits so I’m always wearing them on travel days, leaving more room in my luggage. I do this with pants, too, and outerwear for colder climates.

- Bring snacks. To fill the gaps in both your luggage and your meals during a trip, pack a few protein bars in your suitcase. As you eat them, you stave off hanger-induced meltdowns and create more space in your luggage for bringing home souvenirs. Win win!

Step 3: Plan to do laundry on your trip. You’re going to be washing your clothing at least once during a trip like this - there’s no getting around it. If your travel budget doesn't allow for a laundry service, all you need is a clean sink and travel-friendly laundry soap. I bought these individual packets of Woolite a few years ago and still haven’t gone through all of them. These solid laundry soap bars also work great and don't count as a liquid. You can also buy travel clotheslines, but I don’t usually have much trouble finding hangers and towel or shower curtain rods to drape clothing over as it dries.

If you pack smart and plan ahead, you can still fit a wide range of outfit options in a single carry on bag. The freedom and flexibility this buys you is priceless. Few things make you look as hapless and touristy while abroad as hauling a ton of luggage. And while the rest of your fellow passengers wait idly by the luggage carousel, some half-fearing their bags won’t even show up, you’re already out the door and on your way to your exciting destination. One thing’s for sure - you’re not likely to make the mistake of overpacking twice.

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