How to Pack a Carry-On for Two Weeks


Life, Travel / Saturday, August 12th, 2023

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Once I booked my first flight to Italy, I felt a mix of excitement and also, because I’m me, stress over how in the world I was going to successfully pack a carry-on suitcase for a two- to three-week trip. I love fashion and if I’m going to be in some of the most beautiful cities in the world, I’m going to need a fabulous wardrobe.

But there came a time when I had start thinking realistically. I’ve seen the videos on social media of people struggling with their bulky, heavy luggage down Italy’s cobblestone streets and up several flights of stairs to their Airbnb or hotel room. I’ve heard the stories of checked luggage being lost and people having to wear the clothes they came in for days or buy a whole new wardrobe at their destination. I also know that I’ll be going from plane to train to automobile throughout the trip and want to make my travels as seamless as possible.

Related: This Sustainable Luggage Brand Makes the Most Stylish Travel Products

As a chronic over-packer, I am by no means an expert on how to pack light. I decided to ask my vintage style-loving community on Instagram and Threads for help, and they sure did they deliver. I know I’m not the only one who struggles with how to pack efficiently so I’ve compiled all of the best tips into one handy list.

Along with generally good reminders of what to pack, like, “shoes that are comfy and go with everything,” there were also some ideas that I’d never considered before. While I did ask my community specifically about packing for Italy, these tips for how to pack a carry-on will come in handy for a lot of different trips.

Obviously, the time year plays a big part in this. It’s much easier to pack light during summer, when you mostly wear sundresses, shorts, sandals, etc. However, my trip is during fall, when you need sweaters, pants, boots, and a jacket. My trip is still months away but I feel I should start practicing how to pack my suitcase now. As for what suitcase I’m going to use, I have a few options.

Stylish Carry-On Luggage

Paravel Aviator Carry-On Plus, $425 at Shopbop

Paravel Aviator Carry-On Luggage filled with clothing and shoes

I have both the Paravel Aviator Carry-On and the Carry-On Plus. I love these suitcases for their charming vintage-inspired design and helpful features like multi-directional wheels and an interior compression board with straps.

The Paravel Aviator Carry-On Plus has one extra inch of length than the regular Carry-On, and for me, every little bit of space matters. Paravel claims the Carry-On Plus “fits in most airplane overhead compartments” but I’ve only used mine for road trips so far. Truthfully, I’m a bit worried I’ll be asked to check my luggage at the gate if exceeds the size limit, which would partially defeat the purpose of packing a carry-on only. I want to completely avoid baggage claim, if possible. I’ll report back once I’ve decided.

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How to Pack A Carry-On for Two Weeks

Read on for the tips on how to travel with only a carry-on for a two-week—or longer—trip, from people who have done it.

Pack according to your plans and the weather

“PLAN. Your activities – your outfits. Pick pieces that can go together multiple ways!”

“Hi, I’m from Milan! Flowy dresses [because] it’s super hot, a cardigan if it gets windy in the evening. Fall means rain most day so light sweaters and pants would work.”

Try the rolling method

“Roll your clothes. It helps. Also bring a few pieces that can be restyled.”

“Bring things with thinner or lighter fabrics that you can roll up super small, use rubber bands to tie up thing too & smoosh it down! Rubber band or ponytail, it helps to keep them in place.”

Wear your bulky items on the flight

“I wore 4 skirts, a crinoline, a top and a sweater on the plane.”

“Make the most of your ‘personal item’! I usually bring a backpack. Also, wear your bulky items to fly in.”

Compress your clothing

Vacuum bags, capsule closet outfits, 2 pairs of shoes max, use hotel hair dryers.”

Compression bags. Zipper ones or vacuum seal for way more!”

Plan to wash your clothes halfway through your trip

“I’ve packed a carry-on and a personal item only when I went to Australia for a whole month! I packed enough for about a week and did laundry. I also even packed less because I knew I was going to go shopping for clothes!”

“Bring a laundry soap and just wash clothes in the sink or shower. Hang dry overnight.”

Powder detergent to wash at the laundromat or in the bathroom.”

“Skirts, shorts, tops that all go together, similar colour scheme so they can all be washed in one load!”

Don’t pack a lot of shoes

“The biggest space saver was not packing many shoes. Also depending on where you’re going, heels might be impractical and hard with cobblestone streets.”

“Nice sneakers on a flight and take ballerinas/kitten heels for wearing with dresses. Shoes take space.”

“Ballerinas are the most versatile shoe and consume the least space, + bags that are foldable! One piece bathing suits double as tops and pareos can be used for beach cover up / towel / shawl (I travel Italy out of a carry on for a living).”

Get creative with your packing vessels

“Clothes in shoes, and in any empty containers, like socks.”

“Use contact lens cases for face moisturizers etc. Fill up the empty cups and it’s plenty!”

“We packed an empty backpack at the bottom of the carry-on in case we needed more space other way back.”

Stock up on bath and beauty product samples

This is one of my tips that I’ve seen echoed by travel expert Samantha Brown. A few months before my trip I started collecting any free samples I received like Sephora Beauty Insider birthday gifts, gifts with purchase, PR samples, etc. Now I’ve got a nice little stash of everything from face cleansers to perfume, all in travel-friendly sizes. I would recommend testing out any products you haven’t tried before to make sure you like them and that your skin won’t react negatively to any of the ingredients, especially if you have sensitive skin.

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how to pack a carry-on for a two-week trip