How to Pack in a Carry-on for Multiple Destinations

My teacher salary is earmarked for travel adventures, not luggage. I don’t want to haul around a giant suitcase and I’m not down to pay an additional fee for checking a bag. Last summer I was tasked with packing for back-to-back trips to Colombia and then Belize. So I had to figure out how to pack in a carry-on for multiple destinations.

I spent time exploring Bogota, hiking in the mountains of Colombia, and then headed to the Caribbean Sea for some relaxation and snorkeling. Much of what I wore in Colombia wasn’t needed in Belize and vice verse. Packing in a carry-on for multiple destinations and different climates is possible if you follow these steps.

I’ve also never packed for a guy, so I sought out some advice. The response: The same stuff as a woman without all the extra crap. There you have it, the men’s how to pack in a carry-on for multiple destinations. (Shrug).

School bus converted to a bar with a "No School Today" sign. — Winter break and summer break are ideal times for teachers to travel internationally.

Bringing just a carry-on prevents over-packing and you will never need to fret about something being stolen or a checked bag being lost in transit. Save money and alleviate any worries of missing luggage by keeping your carry-on bag with you the entire trip.

First, I’ll let you in on the secret for how to pack a carry-on for multiple destinations:

Re-wear outfits and do laundry while you’re traveling.

In all seriousness, plan your accommodations so that you have access to laundry after about a week. If that doesn’t work out, hand wash clothes in the sink or relax at a laundry mat for an afternoon.

Check out each of the tips and hints to organize the essential travel items and take the stress out of packing.

Travel Pack Hint: You need less stuff than you think. It's true!

Packing Tip 1: Get the best carry-on bag

Start with a bag that satisfies most airline’s carry-on size requirements. The Osprey Fairview 40 (I love, love, love the Rainforest Green color!) is a top-notch choice for women because it is specifically made to fit a woman’s body and meets carry-on size requirements. It carries like a backpack but opens like a suitcase, which makes finding items a breeze. Check out this review to get the ins and outs of the Osprey Fairview 40. There’s a men’s version too! The Osprey Farpoint 40 has the same features but is built to fit a man.

Alyssa leaning against Nashville mural. Osprey backpack is on floor next to Alyssa — Ready to fly out of the Nashville airport with my Osprey Fairview 40.

Packing cubes have changed my travel life. I like my classroom organized, so there’s no surprise that I want my bag orderly too. Something like these packing cubes that come in a variety of sizes work well. I use one cube for tops, another for pants/shorts, and one for pajamas/swimsuit.

Travel Packing Hint: Bring an empty water bottle and fill it up at the airport.

Packing Tip 2: Select your Travel Capsule Wardrobe

Establishing a travel capsule wardrobe is all the rage in carry-on travel packing right now. A travel capsule wardrobe includes a combination of coordinating clothing items that can mix-and-match to create a variety of outfits. Typically, this is best achieved by selecting a color palette or theme and sticking with that for most articles of clothing. Including primarily neutral colors is a quick and easy way to make sure everything coordinates. Adding in accessories with pops of vibrant colors or patterns brings some pizzaz to an otherwise tame color palette. Having comprehensive travel capsule wardrobe that can mix-and-match is essential for packing in a carry-on for multiple destinations.

Clothes

Be picky when selecting which tops you bring. If it doesn’t fit quite right or you aren’t confident wearing it, leave it at home. Lay out five or six tops (in the same color family) that you like, then narrow it down to the best three or four to pack. Add a light sweater or a cardigan to create a new outfit and provide an extra layer as needed.

Bring a pair of pants and a pair of shorts for a warm-weather trip or two pairs of pants for a cooler destination to wear around town. Also, pack a pair of hiking pants and a shirt for any outdoor excursions. Pants can be re-worn before they’re washed, so don’t over pack pants.

Pick one comfy dress that fits the color theme for a slightly fancier outfit.

Pack one dress in your carry-on — Watching the sunset from a dock in Caye Caulker, Belize.

Don’t forget the clothes you wear on the plane can be worn again, so you have additional options. I didn’t include under garments in this description since I figure you know your underwear needs.

Travel Packing Hint: Bring clothes made of wrinkle-resistant fabric.

Shoes

Every light travel packer I know is going to disagree with how many pairs of shoes I suggest to pack, but to each their own. Keep in mind these shoe options are for city sight-seeing and long hikes through nature. If you’re not planning hikes during your travel, ditch the hiking shoes. Select shoes that coordinate with the color theme in your travel capsule wardrobe for the most versatility.

Cute sandals
Hiking shoes or comfortable flats
Chaco sandals

When exploring a new city, your feet take a lot of wear-and-tear. It’s not unusual to walk more than five miles when sight-seeing, so make sure the walking shoes are comfortable for the ENTIRE day. A pair of super, super comfortable flats that squish down to take minimal room work best.

Sandals take up so little room in the bag, there’s no reason to leave the cute pair at home. A simple shoe change can transform your day outfit to a snazzy out-on-the-town look at night.

Hiking shoes can double as comfortable city walking shoes. Don’t leave these at home if you’re planning any outdoor excursions that require walking; your feet will thank you later.

Chaco’s are a must for me if I’m getting into any sort of natural water; I’m a real wimp when it comes to my feet touching the bottom of the river, lake, or ocean. The brand isn’t important as long as you bring a sandal or water shoe that stays on your foot.

Travel Packing Hint: Wear the heaviest pair of shoes on the plane to create more room in your carry-on bag.

Miscellaneous

Start with a reasonably small toiletries bag to help reduce any excess items that you’re tempted to bring. Everything you need comes in a travel-size version which is perfect when you’re thinking about how to pack a carry-on for multiple destinations. Even this TSA approved razor comes in travel-size with a handy case!

Choose accessories with a purpose. Jewelry and vibrant scarves are small and compact but can bring a pop to outfits in your travel wardrobe capsule.

There’s room in your carry-on for a small travel notebook, book, and laptop computer.

Packing Tip 3: Do a test pack

Relieve any pre-travel stress by doing a practice round of packing at least a week before your travel date. Start by laying out everything you want to bring and take a picture to remember what you need to pack. Wrap your shoes in a plastic bag so your clothes don’t get dirty and place them at the bottom of the carry-on. Roll your shirts and pants to save on space and reduce wrinkles. Make any necessary adjustments to your packing list based on the test pack. Instead of filling unused spaced with extras, save it for small souvenir purchases on your travels.