PACK IT | How I Pack a Carry-On

Hello, hello! Thank you so much for all the love on yesterday’s House Update post! We’re so excited to be back home, and will never take its comforts for granted again! If you missed it, you can see our new floors HERE, and the rest of the remodel projects HERE. I’ll be sure to share more as the house comes back together.

Last week I shared our Trip Report on Vieques, Puerto Rico (see that HERE), and I had a few packing questions pop up. I’ve shared what I pack for a beach vacation (see that HERE), but some of you want to know how I pack it in a carry-on. Because as you know, I strive for that carry-on life whenever possible!

For every trip, I pack both a carry-on suitcase (usually this one or this one), and a personal carry-on bag. The personal bag will usually double as my tote, beach bag, etc during the trip.

We invested in the 22″ CalPak bags several years ago, and they’ve been total workhorses. They’re made to maximize every inch, while staying compliant with carry-on standards. It’s also super lightweight, giving you more leeway to load it up (and easy to navigate in busy airports, train stations, and ferry ports!).

Sugarplum Travel Tip: We have both TSA Pre-Check and Global Entry, and both are literal game-changers when it comes to the ease and convenience of traveling. The hours we’ve saved in security and customs lines is mind-boggling. Well worth the hassle and fee to sign up!

How To Pack a Carry-On //

Okay, so now that you know our bags of choice, let’s get packing! (These tips will work with any similar 22″ hardshell bag.)

22″ Rolling Carry On Suitcase (on sale!)

Since there were six of us traveling, I knew we’d need more than one beach bag, so I packed one, and used the other as my personal item. This has been my beach/pool bag of choice for a couple of years, and it’s still going strong. It holds a ton, and as you can see, packs flat.

I added the tassel to give it a little more personality, and it makes for a cute day bag, as well.

Suitcase | Tote | Removable Tassel

Okay, here’s the important part… the only way I’m able to pack for a week (or even two!), in just a carry-on, is packing cubes!! They have changed everything about packing and traveling for me.

I started with the eBags Classic Set, and quickly added more bags and sizes to our collection as every member of the family utilizes them now. These packing cubes make the most of every possible inch of valuable packing space, keeping items contained and mostly wrinkle free. I’ve tried several brands, but these and these have the best material and strongest zippers.

The key is to fold your clothes to fit the size of the packing cube, that way nothing slides around or bunches up. And pile the clothes high, the breathable diamond nylon will compress them down!

For the medium bags, I fold into one stack, but the large bag has enough room for two side by side stacks. I also separate clothes by category and give each their own cube for easier access once I arrive.

hi sugarplum mexico packing tips
eBag Classic Medium (also like these)

Then you place the packing cubes in your suitcase like puzzle pieces. A 22″ suitcase will fit one large eBag, or two medium eBags on each side perfectly. (It’s worth noting, I took these photos when packing to come back home, when everything was dirty, so I just piled it in the bags!)

On one side, I place the two packing cubes holding my clothes.

Suitcase | Tote | Removable Tassel | eBag Classic Medium

The third eBag goes on the other side, along with my toiletry bags. I put them on the covered zipper side to keep the smaller bags and items in place.

Suitcase | eBag Classic Medium | Clear Zipper Pouches

For most beach trips, I usually just have pair of flat sandals and flip flops, but if I have larger shoes, they fit between the bags like this. Hair dryers and curling irons fit in those spots, too, and along the side (I don’t pack either for the beach).

Any leftover items will usually fit in the little nooks and crannies of the bag. The CalPak suitcases are expandable up to 2-inches, so if my bag is particularly full, I’ll open the expander in order to close it, then compress it down with the second zipper.

hi sugarplum mexico packing tips
eBag Classic Medium

Now let’s talk toiletries. Keep in mind I have TSA Pre-Check, so while I do have to abide by the 3.3 ounce rule, I don’t have to pull them out for security. These clear bags are a recent find, and I really love how compact and organized they keep everything! Rather than one large toiletry bag, I’m able to categorize by makeup, skincare, etc.

Here are the beach essentials I took to Puerto Rico… you know I’m never without my Colleen Rothschild, and her Discovery Kit includes bottles that are perfectly sized for travel.

Sugarplum Travel Tip: Save the small containers and refill from your larger ones, rather than buying all new. Code SUGARPLUM20 saves you 20% site-wide!

Clear Zipper Pouches | Colleen Rothschild Discovery Kit for travel-sized products | Colleen Rothschild Sunscreen (Use code SUGARPLUM20 to save 20% on both!) | Sun Bum Sunscreen | Mini Drybar Brush | Electric Toothbrush| Laneige Lip Sleeping Mask | Olaplex No. 6 Bond Smoother | Supergoop! Unseen Sunscreen | Supergoop! Glowscreen

As for makeup, I kept it super simple! These products were enough to help me feel pulled together, without being overly made-up. But the clear bags, and the suitcase, can fit more!

Amazon Mascara | Eyelash Curler | Supergoop! Glowscreen | NARS The Multiple Stick | tarte maracuja juicy lip

Here’s how I’ve used these bags for the last few trips…

How I broke the pouches down: Masks & Snacks for the plane | Hair Essentials | Skincare | Makeup | Chargers


Okay, now that our carry-on is packed, let’s move on to the personal bag. Most airlines give you one, so you have to make it count! For this trip, I used my new Weekend Vibes tote, and it was great for both travel and beach.

It’s made of sturdy canvas with strong faux-leather straps, and holds way more than you’d think! (It’s also on sale for $17!)

Weekend Vibes Tote (on sale!) | Striped Towels | Hat | Sugar Shack bedroom sources HERE

It held everything I’d need for a travel day… jean jacket for chilly planes, chargers and travel documents, games, laptop, and book. My wallet and other purse items are in the smaller bag, which has to fit in the carry-on since you’re only allowed one personal item.

As for the hat, sometimes I pack it (see how I do that HERE), but often times I just slip it in my bag. That’s the beauty of this hat, too, it holds its shape well, even after a long travel day smushed in a bag!

Weekend Vibes Tote | Hat | Rattan Circle Bag | Jean Jacket | Clear Zipper Pouches | Card Games | Book (this was a great beach read!)

Weekend Vibes Tote | Hat | Rattan Circle Bag | Jean Jacket

Then the tote just slides on top of the suitcase, and away we go!

Summer Nights Maxi Dress (Use code SUGARPLUM15 to save 15%!) | Miller Sandals | Aviators | Initial Necklace | All-Weather Bangles (Use code HiSugarplum to save 15%!) | Suitcase | Weekend Vibes Tote

As you can see, these suitcases have served me well over the years, and I stick with the same formula of carry-on + tote. My travel outfit is pretty much the same, too!

U-Neck Tank | Bring on the Happy Cropped Pants (Use code SUGARPLUM15 to save 15%!) | Jean Jacket | Miller Sandals | Double Strand Necklace (On sale!) | All-Weather Bangles (Use code HiSugarplum to save 15%!) | Tote | Removable Tassel | Suitcase


U-Neck Tank | White Jeans | Jean Jacket | Miller Sandals | Similar Aviators

GxHSP Ruffle Dress | Similar Weekender Bag | Hat

U-Neck Tank | Joggers (Use code SUGARPLUM15 to save 15%!) | Jean Jacket | Similar Crossbody Bag | Leather Tote Bag (On Flash Sale! 15% off with code BACK2SCHOOL) | Aviators

Similar Utility Jacket | Skinny Jeans | Similar Crossbody Bag | Leather Tote Bag (On Flash Sale! 15% off with code BACK2SCHOOL)

White Jeans | Jean JacketSimilar Crossbody Bag | Leather Tote Bag (On Flash Sale! 15% off with code BACK2SCHOOL) | Aviators

For longer trips, particularly international travel, I love this Underseat Carry On Bag!! It holds a ton, has so many pockets and easy-to-access spots, attaches to the handle of your suitcase, and slides under the plane seat!!

White Jeans | Veja Sneakers | Underseat Carry On Bag


Do you see that bag bulging?! Ha, I really stuff it full! This gadget is one of our best purchases and helps keep us under the weight limit. It’s a definite must have for travel.

That’s not to say I never check my bag, but it’s hard to beat the ease and convenience of a carry-on! And the bag I’ve had longest and use most is on sale HERE.

This post is giving me the travel bug, how about you!? Do you have any carry-on tips we should know? Are you headed anywhere soon?


[More Sugarplum Packing Tips]

How To Pack a Hat
What’s in My Carry On
What I Pack for Beach Vacations
What I Pack for Mexico
What To Bring on a National Parks Trip
What To Pack & Wear Skiing
Alaskan Cruise Packing Tips
My Travel Essentials
Travel Q&A, Part 1Part 2Part 3

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