family + business operations for parent entrepreneurs


We're Kevin + Courtney Gilroy: married best friends turned parent entrepreneurs. is the resource hub + like-minded community we were missing in our first days of new parenthood + business ownership.

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How We Travel Carry-On Only

Woman with carry-on luggage

We’re sharing our tips on how to pack when traveling to minimize stress + give us more time to enjoy experiences in our destination.

Created by potrace 1.15, written by Peter Selinger 2001-2017
Reading Time: 9 minutes

Hi OFC Family – It’s Courtney here sharing one of our favorite operations topics: traveling!

Kevin + I made a nonnegotiable commitment to taking at least 1 trip away every year as husband-and-wife before kids. We used this time to reconnect + dream up our year ahead + we consider traveling together vital to our overall success. One of our most recent trips was back to Europe for 3 weeks, which was our most stress-free trip yet thanks to our packing strategy.

We’ve found that packing minimally reduces stress + gives us more time to enjoy experiences in our destination.

We focused on packing as many “double duty” items as possible, slimming down our “technology situation” (do we really need the GoPro, 2 iPhones, an iPad, the laptop, the good little camera, the good big camera + the lenses, etc.?) + to stop packing for “potential weather” by instead simply budgeting for any mini-emergencies (like bringing an extra $5 for a poncho in the souvenir store instead of lugging a raincoat + umbrella just in case).

With those beginning thoughts in-mind, here are the packing commandments we used to make this last big trip more enjoyable by traveling carry-on only:

How We Travel Carry-On Only Pin

Take advantage of laundry services.

Washing a load of laundry is often cheaper than the checked baggage fee you pay for your airlines. If you only need to do laundry once, but might be traveling on a few separate flights, you’ll notice the cost savings really adding up.

For example, we flew into Rome + stayed in the city overnight before boarding the 7-day Norwegian Epic cruise. On Day 6 of our trip, we sent a full bag of laundry out with our room keeper + only paid $20.

We planned our outfits so that any items we would be reusing later in the trip would be clean for wear #2.

Pack in the same color family.

Since we decided to live a more minimalist lifestyle, our clothing color palette was already slimmed down to black, white/ivory, denim blues, + tans. This actually worked out so well for us because we could mix-and-match tops + bottoms without thinking twice.

For the women: take advantage of having 1-piece outfits available.

Dresses + rompers are perfect for carry-on traveling because they are full outfits already coordinated for you, + they’re more lightweight than separates. Because of this, they often pack easier + they’re more comfortable for warm climates. You can easily layer with other sweaters + blazers + tees from your suitcase. 

For the men: invest in comfortable dress shoes.

We still think Adidas designing Cole Haan shoes is one of the greatest things ever. Yes, European style often forgoes American comfort, but there are certain high-quality brands that meet both standards + they are well worth the buy.

My husband was able to explore the cities in dressier shoes, which had an additional benefit beyond double-duty packing: he didn’t stand out like an American tourist in running sneakers!

For the days you will still need a more athletic shoe, check out sneakers made by more formal shoe companies. For example, Cole Haan makes a basic white tennis shoe that can coordinate with pants or shorts of any color.

Pack a black blazer.

Unless you’re traveling for an event with a formal dress code, you can usually get away with dressing up an already-packed “nice” outfit with a fitting blazer.

For me, my blazer acts as my lightweight jacket on other travel days + dresses up for a nicer evening with statement cocktail jewelry. Packing an extra necklace (or tie for the men!) is much more space-friendly in your suitcase than packing a full extra outfit.

One of my favorite ways to use a blazer: throw it on over a short summer romper + change into heels from sandals. So easy!

Pack your fanciest, most-tailored black workout leggings/pants.

This is one of my favorite packing hacks ever! We always end up doing some sort of outdoor adventure activity when we travel, whether it’s apple picking, or horseback riding on the beach, or hiking up Mt. Vesuvius. Most times we don’t even plan those things + they just happen spur of the moment.

In those moments, it’s nice to know I have something quick to change into. But what I love the most, is how wearing dressy leggings that look like regular pants from a distance can actually create perfect outfits. You don’t have to pack multiple pairs of skinny jeans or dress pants, but can instead pair these with a longer blouse or blazer.

If your man owns any of those Lululemon dress pants, these do the same thing as leggings. Just change the shoes + accessories.

Pack a lay-flat or foldable fabric backpack.

I’ll share full details of my personal bag contents in another post, but I basically pack consumable snacks + my wallet/passport + camera in this bag for airport trips + this is what tucks under the seat in front of me. My carry-on luggage goes overhead. 

By the end of vacation, I’ve eaten all the snacks + don’t need the camera. I can put all of that in my carry-on suitcase + store my wallet/passport in the front pouch of the suitcase. One less thing to carry on the way home. This works out really well when living in Boston, because I am usually returning early morning or late at night when I’d want to be wearing one of the heavier items from my suitcase. It leaves more room for the camera or any small souvenirs. 

Try to avoid souvenirs.

I tried to purchase a piece of artwork every time I traveled. That hobby became a bit of a headache. I was dragging my suitcase down cobblestone streets in Venice with a giant cardboard tube holding a painted canvas + sweating my goofy American butt off. It was so awkward the whole way home + I was stressed out trying to keep the tube intact + in sight.

Now, my rule is to either:

1) bring my good camera that I can take great personal photos with + get those professionally printed/framed when I get home, OR

2) hire a photographer abroad to meet us at a destination for a mini photo shoot + we get surprised with the images by the time we’re home, OR

3) pay someone to edit together our family video footage.

If I’m feeling really fancy, maybe all three!

The point is that local artwork is great, but it pales in comparison to documenting the memory of me + my loved ones in that place. I’ve committed to buying a small painting off a street vendor or a gallery in-passing if the moment fits, but I’m done feverishly looking for a breathtaking piece of art that I have to struggle with the rest of the trip to get home. Something to keep in-mind!

Pack an oversized, lightweight scarf.

Okay, maybe this one is my favorite packing hack. 

I always wear a long scarf for traveling because it can double as a pillow + a blanket. I can’t count how many times my long scarf has saved me from freezing my tush off mid-flight.

Our last few vacations to Europe haven’t included many long beach days, so I found that using my scarf as a cover up worked perfectly enough to keep me modest from the hotel room to the water. On a super hot day to Vatican City, my scarf acted as a shawl to cover my shoulders for modesty in the churches.

Pack the multifaceted bikini.

I learned this trick by accident + full disclosure, I’m not sure if this works the same for bigger busted women, but I can’t see why not!

When I realized I forgot my strapless bra in the laundry at home, I had a near panic attack because most of my outfits demanded a low-cut bra. 

Conveniently, my bikini top had removable + changeable straps + all was then right with the world.

I was able to convert to halter top + racer back styles all with one piece of clothing, instead of needing multiple bras.

An added bonus was that the moisture absorbing material in a bathing suit top can sometimes be the more functional alternative to wearing a sports bra under a nice top.

Planning tip: just make sure you don’t pack many see-through or light-colored tops + intend to use this trick with a dark colored or patterned bikini top.

Assess the make-up.

This is where I failed on our last vacation because I ran out of time packing. Seeing how much extra crap I packed bugged me every time I reached in the toiletry bag!

Roll with the “I’m on vacation” look. This doesn’t mean you need to look like a hot mess, but it does mean go with your natural hair style + pack multipurpose makeup.

I haven’t found an organic alternative to the Anastasia contour kit, but I have always loved this set for its versatility.

I just pack my tinted moisturizer with SPF, the contour kit, mascara + 1 lip gloss. I always mean to get lash extensions ahead of time, but they always fall off the priority list last minute! Next time. Maybe. 

For skincare: I pack moisturizing makeup remover cleansing towels + a refillable travel tube of sunscreen. Normally, we eat our sunscreen, but vacation diets don’t often offer what we need to do that. So, we apply the lotion sunscreen for trips! Then deodorant for the both of us + 1 unisex cologne sample-size that we share.

For dental care: Individual toothbrushes, travel size toothpaste + floss. Always flossing!

For hair care: I pack a brush + use the toiletries at the hotels. If I’m worried about the hotel toiletry quality, I pack a sample size hair mask for halfway through vacation.

Accessorize with 2 sets + no valuables.

I pack 1 full set of gold jewelry + 1 full set of silver jewelry. Earrings, necklace, bracelet, watch. Nothing else. No wedding bands or engagement rings.

Make the smartphone work smart for you.

We use the TripIt Pro app for planning extended vacations with multiple destinations + reservations. We also always keep a digital document copy of our expanded itinerary in our phones (not just on the iCloud). 

Before kids, I used the StyleBook app, which lets you take blogger-like images of your individual clothing + create unique outfits on a calendar. It tracks what’s clean in your closet, how many times you’ve worn something + acts as a great closet inventory when you’re out shopping + wondering what you need or already have. I styled all of my trip outfits on this in-advance, so I just woke up + knew what to grab everyday. I don’t have the time to update my closet contents with young kids lately, but if you travel frequently + have an in-home helper, then this might be worth outsourcing to your helper to do!

Note: I always print a paper copy of our passports for us to keep as backup, too. 

What was cool about this particular packing strategy was that it allowed me to pack for the south of France in summertime + also the camping trip around Iceland all in one carry-on suitcase. I feel like if we could pull that off, this strategy should work for most vacations!

We’d love to hear from you: How do you pack for long trips? 

What are your favorite tricks? How has your travel changed upon having kids? 

I’ll keep adding to this list as I recall different tips.

If you’re a family-centered entrepreneur + travel enthusiast, then be sure to subscribe to our newsletter where we share our smart family + business operations, including our personal family trip planning guides (like the Disney Family Travel Guide).