How to Pack Two Weeks in a Carry-On

I don’t think I”ll ever claim to be an expert at packing. I feel like unless you travel really often (like my husband does for work), you kind of get out of practice. But while I may not be fast at packing, I have mastered the art of it for long trips—starting early, strategically planning outfits, editing things down. No more overpacking here! It’s become a proud accomplishment to be able to pack for two, even three, weeks and multiple cities in a single carry-on suitcase. My husband gives me a gold star for my effort, we don’t have pesky baggage fees, and we never face the dreaded lost bag situation. And once we arrive at our destination (or home), we’re on our way—no waiting around the baggage carousel.

What about you guys? Are you a chronic over-packer or a carry-on convert? After our most recent trip to here and here, I snapped a few photos of what I packed so I could share my process with you. This is Part 1 of two posts, and hopefully it will help when it comes time for your next adventure. Maybe you’ll even get a little vacation outfit inspiration too. See what’s in my travel tote and my tips on how to pack for two weeks (and two cities) in just one carry-on!

Travel Tote Essentials

First things, first. Grab a bag–like this one by Madewell–that can fit a lot of travel necessities you’ll want on hand…

  • A versatile sarong for the beach/pool that doubles as a scarf and triples as a light blanket for the plane
  • Snacks (I like almonds and apricots) for hunger pangs in between meals
  • Sunglasses in their case means no scratching
  • Emergen-C for fighting off colds before and during the trip
  • Headphones for jams on the plane or beach
  • iPhone for Instagram and Spotify…but not email or work!
  • Thick socks for keeping toes warm on the plane
  • Passports (I carry his, too)
  • Journal for jotting down favorite spots and memories
  • iPad for watching movies on long flights
  • Pen and highlighter for last-minute travel research
  • Travel guides and a folder with reservation info and printed pre-travel research
  • Books to read leisurely
  • Wallet with a bit of cash
  • A big pouch to put all the little bits and pieces in

Note: When traveling with a laptop, I use a more structured bag (Lo & Sons O.M.G.).

You may be wondering about cameras, lenses, memory cards, phone power cords, outlet adapters…my husband packages all the small pieces into Ziploc bags and carries our gadgets in his personal item (usually a backpack).

10 Tips for Packing Light

  1. Research your destination. What will the weather be like? Are there any cultural sensitivities – is there any clothing not acceptable in certain places (ex. temples, churches, museums)?
  2. Consider your activities. We did a lot of city walking, excursions and beach time during our last two trips. I didn’t bring a single pair of heels and instead opted for cute flat sandals that could transition from day to night.
  3. Plan out your outfits. It’s totally worth the effort and helps prevent overpacking. Pick versatile pieces you can mix and match for different looks. Bring a few accessories to dress things up, but nothing you’d be heartbroken about losing.
  4. Pare down your makeup and toiletries. How much time do you really want to spend doing your hair every day? Skip the heavy, bulky hairdryer and curling iron for sure. Let your hair air dry if you can—and the top knot can become your best friend.
  5. Tightly roll everything. I mean, everything. Rolling takes up less space than folding and minimizes wrinkling.
  6. Layer heavy to light. Shoes first, then heavier rolled clothing (jeans and pants). Lighter materials, especially linen or silk, should be added last.
  7. Reduce your shoe count. Cut back or at least pack shoes that fold very flat. For warm-weather getaways, I pack a pair of sneakers or Toms, a ballet flat, and one (or maybe two) sandals. Cheap flip flops too.
  8. Stuff the extras. Underwear and swimwear can be pushed into an interior pocket. Tuck jewelry in a small pouch or right into a clutch.
  9. Strategize your quart-sized bag. Figure out what your most-needed toiletries are and only what fits in the bag goes. Place it in the exterior pocket of your suitcase for easy removing in the security line.
  10. Don’t forget to leave a little space. A little room in your suitcase and personal item means room for a few travel treasures to bring home.

A note on my travel outfit — I wore a few extra layers while traveling (see image outfit above), since we left with snow at home and returned to it. Thick black leggings and a black tank are my comfortable staples, I just make them airport appropriate with cute flats and long layers on top.

What are your travel tricks? I’d love to hear! Feel free to ask questions about any of the specific items pictured – I’ll gladly answer!

*Also see 12 warm-weather vacation outfits I packed for Mexico and Colombia using these tips! 

  • share this post:
  • anna sheinberg ∞

    Where did you get that makeup bag? I absolutely ADORE it!

  • PerpetuallyChic

    Hi Anna, makeup bag is Sonia Kashuk for Target! The pockets outside & inside are so great. Mine’s a few years old now, but looks like they have it in a couple different colors – black, navy, purple, green:

  • Tina

    Is your travel tote the bag you also took with you whilst out and about during your trip?

  • PerpetuallyChic

    Hi Tina, exactly! That Madewell tote is perfect for travel and by day, especially when visiting markets or the beach when you want to carry a few extra things.

  • Love this! I have a few big trips coming up and am desperately trying to figure out how to pack in a carry on ONLY. Luckily warm weather locales make it a bit easier!

  • PerpetuallyChic

    So glad you found my tips just in time for your upcoming trips!

  • ltp

    Where did you get that big pouch for your tote!? It’s fantastic!

  • PerpetuallyChic

    The pouch was from Anthropologie, a year or so ago!

  • Sharon Winkler Moren

    I have been a carry-on convert for years for shorter trips but am now branching into 2 weeks+ and that and a Nexus card make arrivals and departures a breeze. We have done the lost luggage thing as well as experienced a broken luggage carousel and lightening keeping baggage handlers indoors. Not fun when you just want to get to your hotel (or home). I try to save my “personal” item for my electronics and a jacket/wrap as well as souvenirs

  • PerpetuallyChic

    Great tips, Sharon. I always leave room in my personal item for souvenirs, too!

  • I’m going on a trip soon and this was super helpful! Thanks!

  • toronto

    What brand is your carry-on luggage?

  • PerpetuallyChic

    Hi! I just use a black Swiss Army suitcase. Nothing too fancy since they get so beat up in transit. I get them at Target and replace every few years.

  • Monika

    Hi There! I have just stumbled across your blog and love it 🙂 2 Quick questions: 1) Where is the jacket from that you wore on the plane? 2) Where is the grey comfy top from that you wore on the plane? Is it a sweater or cardigan? I’m heading out of town in about 10 days, and I would LOVE to wear both of those items! Thank you XO

  • PerpetuallyChic

    Hi Monika, the jacket and sweater are both J.Crew! Get the jacket here: The sweater is out of season, but I also have this gray cashmere hoodie and love it for the plane (on sale now too): Happy traveling!

  • Monika

    Thank you SO much! You rock 🙂 and BTW, I love reading your blog now that I’ve discovered it XO

  • Eddie Q

    I have to travel to 4 cities in 2 weeks and I have no time to place the luggage under the plane…. I like your “ROLL” your clothes strategy. I’m going to try that.

  • Sophie

    Excellent strategy…. Any suggestions for packing/bringing a snorkel gear (mask, tuba, fins)?

  • PerpetuallyChic

    Good question – I’ve never packed snorkel gear but I’d imagine it would be best to layer it on the very bottom of your suitcase then build up from there!

  • Chelsea

    I’m disappointed you modified this post – I had it bookmarked and wanted to review it again before I pack for an upcoming trip. I miss the older post that had much more detailed information. Any chance you still have that saved somewhere?

  • PerpetuallyChic

    Hi Chelsea, glad to hear you bookmarked the post. The only modification I made was to split out the actual outfit images and list into a separate post, which was more conducive for the design of my newer website. If you look at the very last sentence of this post you’ll see there’s a link to that–otherwise you can click through directly from here: Thanks!

  • Zoe

    Hi there Perpetually Chic! Good tips and love the note on travel outfit. It works out perfectly:) I travel every other week and use these tips plus I have found that garments from designer Autumn Teneyl are so packable that you can pull them out of the bag and wear! They just do not wrinkle and they mix/match so you can change it up easily. For any of you perpetually chic gals you might want to check out her portal to get some ideas too… Happy trails! Z

  • grbarclay

    I absolutely love this post as I’ve been searching for some tips on packing for a tropical vacation in only a carry on. We have some really tight connecting flights to catch and I don’t want to risk waiting for luggage!
    I’m curious as to how you pack your beach hat without crushing it! And also, your erase paste and smith’s rosebud lipgloss… Is that considered a liquid which needs to be added to your liquids Baggie? I use the same products so knowing that in advance would be super helpful!
    I love your blog since stumbling upon – thank you!! xx

  • Awesome tips! Constantly trying to master carry-on only travel and am slowly converting. So much easier getting through airports and getting on your way!

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