How to Pack Everything in A Carry-On

There’s nothing worse than missing a connection and realizing that your luggage is who-knows-where while you’re in a hotel halfway to your destination! Or arriving safe and sound in your intended destination while your bag has gone on holiday somewhere else! All that worry and focus on retrieving your carefully packed luggage takes up precious vacation time. The clear solution is to keep your luggage with you. Plus, packing it all in a carry-on prevents you from overpacking and having to cart and carry heavy luggage around on your trip!

But how on earth do you pack everything you need into one small carry-on? This question baffles so many travelers and often discourages them from even trying. Don’t worry! It can be done, even for very long trips. And we’re here to walk you through every step:

What to Bring

What you need to bring will be different for every trip, but there are some top tips and general rules to follow. It doesn’t matter if you’re heading out on a 4-day beach excursion or a 14-day European Adventure, always keep these tips in mind when packing:

Clothes

three women ( Ann and Kristy) toast white wine in front of Villa Laura in Tuscany

Pick a color palette. You don’t have to wear only neutrals but sticking to a color palette will help you maximize the mix-and-match ability of your wardrobe. Think of it as a mini-capsule wardrobe.

Choose wrinkle-resistant clothing. Even in cold climates stick to breathable fabrics, that don’t wrinkle easily.

Layers layers layers. Rather than trying to pack a bunch of bulky sweaters, try to stick to layers. They give you versatility for sudden weather changes.

[Photo Credit: Ann via Shared Adventures. Packing layers and light accessories like scarves prepares you for all kinds of adventures! Read about Ann’s Tuscany adventure here!]

2 Pairs of shoes. You should have one pair of walking shoes ( which you will wear on the plane) and one pair of nicer dress shoes OR sandals if it’s a beachy holiday. Make sure your dress shoes are still comfortable to walk in and your walking shoes are nice enough to eat out in.

Do laundry. Depending on the length of your trip, pack for only 5 days and plan on doing laundry about halfway through.

Toiletries

Everything should be mini! Remember, there is no reason to bring a full bottle of anything. Aside from the airport security 3oz rule, you aren’t going to use a full bottle on your trip. Put all toiletries in mini bottles, use samples, and take half a bar. Or plan to pick up some new toiletries at a local store when you arrive.

Just the basics. Try to shrink down your cosmetics and skincare items to the basics.

Packing cubes/ Compression bags

We love using these for organization and for maximizing space. We’ve found a combination is best. Use compression bags (no vacuum required) for your bulkier items and anything that is truly wrinkle-resistant. Use packing cubes to organize the rest.

Pro-tip: If you’re traveling to several destinations with different climates– pack your cubes according to the destination rather than category. That way in each new destination you just need to unpack one cube!

Visualize Your Carry-On

5-7 Days Before Your Trip

This may seem early, but having more time to consider and think about your packing choices will help ensure you’re only packing what you really want to bring. Often your first ideas of what you should pack are not your best ideas.

1) Look up the weather. This is the biggest factor in your packing decisions.

2) Make a list. Use an app like PackPoint or old school pen and paper. To start, write down the essentials. Medication, toothbrush, underwear, etc. Then, fill in everything else you want to bring. Focus most on the activities you’ll be doing on your trip.

3) Check the airline’s bag requirements. Each airline has slightly different dimensions and weight requirements. So, double-check that you know what those are and that your bag fits within them.

three piles of folded clothing and a woman's hands as if packing them

4) Lay it out, try it on! Lay everything you want to bring out on your bed. Then start trying it all on! You want to plan out your outfits as much as possible. See how many can be mixed and matched, make sure you feel comfortable in your clothes, and that they all go together. Generally, we try to stick to the rule of 2-3 tops for every bottom. Pick clothes you can wear more than once.

[Photo Credit: Sarah Brown via Unsplash]

5) Pare it down. Get rid of anything that can only be worn once or only with one specific item and anything you’re not 100% comfortable in. Get rid of anything that cannot be worn for at least 2-3 of your planned activities. There’s no need to pack for “just in case we go to a ball” or “ just in case I decide to get up early and go for a 10-mile hike”. You’ll probably know if you’re doing something like that ahead of time.

6) Ruminate. Set everything aside to think about it.

Packing

2-3 Days before your trip

It’s time to start packing in earnest! You’ve had time to mull over your outfit choices and make sure you’re truly happy with them. Now let’s get them to fit into your carry-on!

1) Look up the weather just to make sure there aren’t any major changes.

2) Get your checklist and lay everything back out on the bed.

3) Go over everything you want to bring one more time and make sure there are no “ just in case” items.

4) Set aside essentials. Anything you’ll need on the plane: your flight essentials kit, medication, kindle, phone charger, important documents, wallet, liquids bag, etc. Also set aside your travel outfit, bulkiest jacket, and bulkiest shoes.

First Layer

5) Start with your bulkier items like jeans, jackets, and sweaters. Roll them as tightly as possible (consider using a compression bag) and layer them in the bottom of your suitcase.

6) Next take your most wrinkle-resistant items and roll them up in a compression bag for the bottom layer. ( If you’re not using a compression bag, roll them tightly and place them in the bottom layer.)

7) Add your shoes. Just one pair of nice shoes OR sandals. Arrange them so that the soles are facing the side of the bag and the soft side is inside. If possible, stuff the toe with socks.

8) Fill in any gaps or spaces on the bottom layer with socks, cables, chargers, belts, hats, scarves, medications, spare batteries, or any other small items.

9) Put all your non-liquid toiletries and makeup in their pouches and layer on top of your bottom layer to maximize cushioning and prevent breakage.

Pro tip: Place a cotton round in between your pressed powders and the lid to help prevent breakage.

Second Layer

10) Fold and/or roll ( depending on wrinkle resistance) the remaining tops, dresses, and pants into packing cubes. Place bras, underwear, and remaining socks in a cube of their own. Layer these cubes on top of toiletries.

11) Fill in the gaps with any remaining extras ( belts, hats, scarves, chargers, socks, etc)

12) Throw in an extra compression bag for your laundry.

13) Look at how it is all fitting together. Re-arrange as needed. You may find that your sweaters or jeans take up less space when folded. Or that you have an extra gap in the bottom layer that can be filled. This is a game of Tetris and you may need to shuffle things around to optimize it.

14) Close your suitcase!

Final Checks

15) Pack your personal bag. This should be bigger than your usual purse – think a large tote or small backpack. Include your flight essentials kit, important documents and wallet, liquids bag, phone charger, and fragile electronics (camera, computer, etc).

people walking down the cobblestone streets of Bologna

16) Take it all for a test drive! Even with door-to-door services, you’ll have to do some walking with all your luggage. And probably on an uneven surface. So, roll it around, take it upstairs, lift it, take it down the street. Check out how the wheels are rolling on uneven surfaces. (if it’s a soft bag you may have to check weight distribution).

If you find yourself getting overheated, frustrated, and exhausted then you have packed too much! Go back to the beginning and consider what you can do without.

[Photo Credit: Ann via Shared Adventures]


With the right attitude, a minimalist approach, and careful planning you’ll find it’s quite easy to pack it all in a carry-on! Try to leave some space for souvenirs. And remember, if you can’t picture an exact moment on your trip when you’ll need or wear something — you can leave it at home!

If you’re feeling confident in your new packing skills and are ready to plan an adventure to go with them, let us know!

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)