These tips, products helped me pack for six-week trip in a carry-on

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I almost always checked my bag until a few years ago when it took 90 minutes for my bag to arrive in Atlanta. We were told first informed our bags were on carousel 1. No, it’s on carousel 9, the back to 1, then back to 9. Several of us were racing back and forth between carousels like we were doing soccer drills for Atlanta United.

That was around the time that lost luggage rates were soaring. In the summer of 2022, 16,000 suitcases (mostly black) were left stranded at Schiphol Airport in Amsterdam.

So I refined my packing skills and packed for a six-week trip to Portugal in my new Away suitcase, further motivated by the fact we had a layover in Amsterdam and I wanted to make sure my pretty new suitcase was not going to be joining the lost luggage party there.

It took me a while to pack but I did it and for the first 2.5 weeks when we were traveling from Faro to Lisbon to Porto, all went well. The only problem I encountered was when we got to Lagos, our home for a month.

Before we left I had checked the weather for Lagos for the month of October and temperatures were reported to be highs in the 70s. But when we arrived, the temperatures were in the 80s and it was hot.

I took the right amount of clothes but not the right clothes for the weather. Instead of the cozy knit pajamas I brought, I slept in one of my husband’s T-shirts and my merino wool sweater that was going to keep me warm at night when the temperatures were supposedly in the 50s sat unworn in the closet.

But packing for those six weeks taught me some things about packing light and I discovered some useful products for packing for a long trip.

All of these tips are meant for travel by plane but can also be useful when taking a road trip.

Select clothes that travel well

Because I travel so much, before I purchase an item I judge it on its travel-worthiness. Will it wrinkle easily? Will it go with other things in my closet?

I love linen clothes and took several items with me on a trip to the South of France. We traveled around Provence, staying in several hotels. Not one of them had an iron. Lesson learned: Linen is the worst fabric to take on a trip.

Except for special occasions when you don’t mind doing a little ironing or need that taffeta skirt that takes an hour to iron, try to find clothes that you can roll up then just pull out, put on and go.

Another thing to remember: the darker the clothes, the less the wrinkles show.

Take clothes that serve multiple purposes

Think about taking a workout top that you can also wear with jeans, a pashmina that can be used as a scarf or to wraparound a bathing suit, or a pajama top that can be a workout top. Unless you need an item for a specific occasion, like a wedding, formal night on a cruise or another elegant event, avoid taking an item of clothing you will only wear once.

Select small versions of hair tools or ones that serve multiple purposes if possible

Sadly my beloved Revlon hair dryer that helps smooth my frizzy hair was too large to take to Portugal so my hair didn’t look its best. I took this combo curling iron/flat iron instead to save space.

If you are traveling internationally, make sure any tools you take are dual voltage.

Use the 5-4-3-2-1 method of packing

Have you heard about the 5-4-3-2-1 packing method? This means you pack

• 5 tops 
• 4 bottoms
• 3 dresses and three pairs of shoes 
• 2 swimsuits and two bags 
• 1 hat, one watch, and one pair of sunglasses

I don’t strictly follow this – with my Fitbit I don’t wear a watch any longer. Plus, this doesn’t mention pajamas, underwear or workout clothes.

But the concept is good. You don’t need to take 10 tops with you or more than four pairs of pants or skirts.

Here are the items I always take: a pair of jeans, a pair of black pants I can dress up or down and a black cardigan that I usually wear on the plane. I take one pair of pajamas that roll up small, 5-6 pairs of fast-dry underwear, one pair of yoga pants and one workout top.

Here are a few options for quick-dry underwear that work well on a trip. I also like these boxer brief style of underwear by Woxer that are great to hide panty lines and lessen chafing.

One year I was on a family beach vacation and found out we were all going to my nephew’s baptism.  I had not packed any church clothes and ended up wearing a bathing suit cover-up. Ever since then I always pack a dress just in case.

For a complete list of what I took to Portugal and why the Away suitcase is my favorite, please see the related story: Which of these 3 suitcases is the best carry-on? If you decide to get an Away suitcase, email me at jan@the100companies.com to save $20.

Get used to wearing the same outfits more than once

Even if you are traveling with the same group of people, you can wear the same outfit more than once. I promise. Most likely no one will notice, and if they did, wouldn’t care.

I wouldn’t go as far as the Steve Jobs philosophy of fashion, which involved wearing the exact same outfit every day – black turtleneck, Levi’s jeans and New Balance shoes – but dressing simply and putting outfits on repeat are helpful when packing for a long trip.

Pack shoes and handbags that can go with multiple outfits

For me shoes are the hardest part of packing. I used to think men had it so easy as they can pack one or two pairs. But then I had a business lunch with a tall man once and he said, “I wear a size 13 shoe. I add one pair of shoes to my suitcase and it’s already a quarter filled.

When I went to Portugal I took tennis shoes, flats and sandals. The tiled sidewalks of Portugal made it a little easier to decide because you cannot wear heels there without risking a broken ankle or at the very least, an embarrassing fall on your butt when you slip on the slick tiles.

White tennis shoes are  in fashion in the U.S. and in Europe with many women wearing them with dresses. These lace-up sneakers from Cole Haan are a comfortable, fashionable choice.

I love Skecher shoes and have several pairs. The Cleo Bewitch Ballet Flats are my favorites and were one of the pairs I took to Portugal. They are so comfortable and go with dresses and pants. They come with me on just about every trip I take.

I love the Taos brand of sandals and have worn a pair of The Show for several years. These also look nice with dresses and pants.

Purses can be a challenge as well. My favorite bags to take are the foldable Longchamps bags. I have the navy bag in the medium and large sizes, taking either one or sometimes both. They are durable, lightweight and fold flat.

After a few years the corners of my larger bag started to wear out. I turned it inside out and sewed it back together and still use it.

Tip: If you travel internationally look for one in the Duty-Free stores and save yourself the sales tax.

Another bag I love is the Travelon anti-theft messenger bag. It comes in five colors, folds flat and has a side pocket for a water bottle.

I sometimes travel with a small bag if I feel like I need something a little dressier. My splurge bags are Tory Burch and I take one similar to this that’s large enough to hold my phone and a pair of glasses.

Wear your bulkiest shoes on the plane

If you are taking a heavy pair of shoes with you, wear them on the plane. If you are traveling for several hours and don’t want to wear them the whole time, slip them into a plastic grocery bag and put them in the overhead, replacing them with a pair of slippers you packed in your carry-on.

These cute foldable ballet flats come in 45 colors for less than $17 and can also be used in your room during your trip. Please don’t wear just your socks or heaven forbid, bare feet on the plane!

Take a foldable tote for items you buy during the trip

We checked bags for our return home from Portugal for a few reasons. One, we had bought a lot of port to bring back for a friend and two, had picked up some items during our trip. Plus, we didn’t care if our suitcases were delayed on the return trip.

I always take a foldable tote or duffel bag that I can check on the return flight if I need to. Here are several duffle bags that will work for this purpose.

If you do take a hat, here’s how to pack it

I generally travel with a hat. A ball cap is easy to pack but a larger straw hat or fedora style? Not so much. To pack your hat, turn it upside down in the suitcase and pack items around it.

You can also get one of these hat magnet clips if you prefer to keep it with you.

Take small packets of laundry detergent to wash clothes during a long trip

I like to use these small packets of Tide detergent. I use them to wash a few pairs of underwear every few days.

Don’t forget the power of spot cleaning. Just because you drop a dollop of sour cream on your jeans doesn’t mean you need to wash them. Grab a washcloth and a bit of soap and just clean the spot.

Think about splitting toiletry items into two bags

I used to travel with one large toiletry holder with my makeup and all my toiletry items. Then I started splitting them into two smaller bags and found them easier to fit into my suitcase.

I use two Vera Bradley bags. The smaller one holds my make-up while the larger one has items like shampoo and toothpaste.

Get travel size versions of your toiletries or downsize into travel bottles

Bed, Bath and Beyond was my go-to for small versions of toiletries, but sadly the store is no more. Drugstores and dollar stores are good for some items. I stock up on a TSA-friendly size of Crest toothpaste at Dollar Tree, also a great place to get toothbrushes.

I love this set of travel-size products from CeraVe with four skincare products. And this is a good toiletry set for transferring your products to. It comes in 12 color combinations for $10.

To make the most of your packing space, use compression packing cubes

This is my #1 tip for packing for a long trip. I started using packing cubes a few years ago and it has made all the difference in making packing easier, moving from place to place and for no real reason I can figure out, unpacking less unpleasant.

I use this set of compression packing cubes that allow me to fit even more. Roll up your clothes and place them in the bag. Zip the first zipper closed, then the second one that compresses the clothes to make more space.

I put socks, underwear and pajamas in one, shirts in another and pants in yet another. I find items more easily and when we switch accommodations, I just throw them back in the suitcase.

Pick a personal item that works best for you for a long trip

Your personal item needs to multi-task on a long trip. It has to carry all the items you need during your plane ride plus all the things you couldn’t fit in your suitcase. There are so many types of personal items – from backpacks to tote bags to duffel bags – that choosing one can be an issue.

For my trip to Portugal I had a tough time deciding, but finally picked this Kroser backpack, which is a steal at just $21.

Please see the related story: I tested three bags for my personal item and chose this one

The other personal item I love and that I use when I need to carry more is this weekender bag. I love the compartment on the bottom that holds several pairs of shoes. This bag comes in 25 patterns and is less than $40. This is the second of these bags I have owned. My husband kept taking my first one so I had to buy another. Are you seeing a pattern here?

Here are the items I take in my personal item.

Pashmina
iPad
MacBook
phone
water bottle
charging cables
tissues, eyedrops, lipstick in small case

Bose noise cancelling headphones. Yes, they take up extra space but by cutting our excess noise, they make flying so much more enjoyable they have earned a spot in my bag.

For international trips, I take this passport wallet from Etsy with a built-in charger.

It’s not easy packing for a long trip in a carry-on but I was so happy I did. It was much easier to get around on the trains we traveled on and when we reached Lagos, we could walk from the train station to our apartment.

And I didn’t get tired of wearing what I brought. I was fine wearing the same things over and over. Which means I should have gotten rid of the 85% of the clothes in my closet I never wear, but that didn’t happen. But I did feel empowered that I was able to travel with fewer items and hope you can too.

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— Jan Schroder