How to Pack for a Multi-Month Trip in One Carry-On


The difference between packing for a week and packing for a month isn’t really that big, but the idea of remembering everything you might need is daunting. (Photo: Pamela Pamela MacNaughtan)

By Pamela MacNaughtan

Packing for a multi-month trip is always a challenge, there are so many ‘what ifs’ that come into play. I’m going to Southeast Asia, but what if I need to do a visa run to a place that is colder? Surely I need at least a few pieces of warm clothing. What if there is a party? I really don’t want to look like a dirty hippy. So what do I pack? And how do I pack it all into a carry-on sized backpack?!

The key to packing for long-term travel is to select items that offer you variety. Admittedly, this takes some thought; a week in a carry-on is no problem, but a multi-month trip becomes a little more challenging. Here’s what I’m taking when I leave for my extended travels through Southeast Asia, and why I chose it:


Items that have multiple uses are ideal. I tend to visit a lot of temples and other sacred sites when I travel, so skirts are perfect. The ones I chose are mid-length or ankle-length, and are neutral in color so I can wear them with anything, plus skirts can be dressed down with flip-flops, or dressed up with a pair of ballet flats. Use the same tactic with shirts. A nicer looking black T-shirt can be casual when you want it to be and dressy when you need it be, with the addition of a scarf or a lightweight cardigan. Which reminds me: Pack a scarf and a lightweight cardigan.


Small and flat is the key here. I used to travel with only one pair of flip-flops, which worked great until I was in the middle of a walking tour in Warsaw and my right shoe strap broke. Now I am more prepared. I have a pair of black plastic Havaianas, plus a slightly nicer looking pair of black flip-flops made with cloth straps.

I also pack running shoes for hikes and hill treks, and for nicer occasions, lemon-yellow patent ballet flats from Tieks, which are designed to be folded in half so they can fit in your purse.

The beauty is that I have four pairs of shoes and they take up very little room. Plus I can stuff things into my running shoes. More storage space!

Watch: A New Way to Pack a Carry-on Bag Like a Pro


Accessories are magical. Truly, they are the best way to change the look of an outfit. (I love them because they remind me that I’m a woman, and I can look pretty while I’m traveling —instead of like a hobo.) As with your clothing, every accessory you pack should be able to multitask, so pick versatile items. These are my own favorites:

  • Cornsilk yellow scarf: for those cold travel days, as well as dressing up a bit for nice restaurants, temple visits, etc.

  • Multicolor infinity scarf: for days when I need to wear something that is not yellow. Seriously, that is the only reason.

  • Fake pearl and diamond bracelets and earrings: costume jewelry is the easiest way to make something look a little more dressy.

  • Large winter toque: it’s my favorite hat, and while it will be too hot to wear this on most days in Southeast Asia, I am still bringing it. I freaking love this hat. I’ll just have to go into the mountains or somewhere cool so I can wear it more often while I’m traveling.


I’m a no-fuss type woman, but I have naturally curly hair that needs decent shampoo and conditioner. So I pack a travel size of my favorite Kiehl’s hair products, as well as some hand lotion. I also have deodorant, a razor, a toothbrush, and toothpaste — and that’s my entire toiletry pouch.

I have a basic make-up kit for this trip too: black liquid liner, mascara, copper glittery eye shadow, lip gloss, and hair ties. That’s it. If I need something else, I can buy it. And honestly, this is more than I’ll probably need: I hardly ever wear make-up. Mascara and lip balm are generally all I use, but if I’m going to an event or party on this extended trip, I want to look nice.

Related: Confessions of an Overpacker

Tech Gear

As a travel writer, blogger, and photographer, I tend to hit the road with a little more gear than most. In addition to the basics (an adaptor, a flash drive, and various wires and chargers), this is what I’m taking this time around:

  • Camera: After a couple years of dreaming, I have finally bought my dream camera, the Fuji X-T1. I love the Wi-Fi connectivity as I can quickly send a photo to my phone to edit and share on the fly.

  • Tripods: I bring a compact little guy (I like Manfrotto) that’s small, light, and super easy for packing. It’s good for getting really low, as well as setting up my camera on some rocks. Basically I use it for shots that won’t work with a regular tripod. For those, I bring another Manfrotto product, which is bigger but still fits in my backpack or a cross-body bag.

  • Unlocked iPhone: I have a 5S, and it’s in good condition so I don’t plan on upgrading it anytime soon. It’s also unlocked, which allows me to buy a local SIM card and data plan — a cheap task in Asia.

  • Laptop: I used to have a MacBook Pro, but it was really heavy to carry around. The 11-inch Air is the perfect weight for travel, and most people don’t even realize I’m walking around with a laptop in my bag—which makes it a safer choice too.

  • Portable charger: I always carry a phone-charging cord and plug with me, but having an additional portable charger is a lifesaver, especially when I’m on the go and need to be on social media a lot during the day, or have photos to edit.

  • External hard drive: I put all my photos on a WD My Passport external drive once they’ve been backed-up to the cloud and imported to my online portfolio. The great thing about this model is that I can connect to it wirelessly (without internet) to my laptop and transfer files. It’s a beautiful thing.

Related: Save Your Data — Cheap Ways to Text and Call While Traveling

How to Fit It All In

When I start stuffing clothing into my bag, I use the rolling technique and separate items into packing cubes. It’s easy and keeps the inside of my back in control. It’s also part of my anti-theft plan. Say what?! You see, on travel days my clean clothing is in packing cubes, usually toward the bottom of my pack, and my dirty, smelly clothes are on top. It’s my hope that someone won’t rummage through nasty clothing to steal something.

Now, who wants to start the betting as to how soon I get sick of the clothing I packed?

WATCH: How to Dress for the Arctic in 13 Easy Steps

Let Yahoo Travel inspire you every day. Hang out with us on Facebook, Twitter, Instagram, and Pinterest.

Check out our original adventure travel series A Broad Abroad.