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How To Pack for a Warm Weather Vacation in a Carry On

January 20, 2020


Erin Schrader

January, you’ve quickly convinced me it’s time to head south. While I usually love you for your snow, this year you’re letting me down, so I’m looking for sunshine and palm trees ASAP. I travel a decent amount, and I’ve learned through the years what works and doesn’t work for packing a lot into a little space. As thrilling as it is to see how close you can get to that 50 pound limit for checked items, I’ve been curious to answer the question “can you actually pack everything you need for a week away in a carry on!?” Well today we’re tackling just that – how to pack in a carry on.

I’ve heard the stories, but I’ve never believed that it could be true for me. I’m typically that girl rollin’ 100 pounds through the airport and then when I get to my final destination I realize I packed about 72 shirts too many. With 2020 being the year of challenging myself, I went out on a quest to do just that and well friend, the answer is in and the good news is – it’s possible. With many of you planning for warm weather getaways over the next few months, I wanted to share how I strategically packed to fit everything in a carryon. Turn that checked bag money into cocktails on the beach money! Pass the pina please. Before we dive in, if you’re looking to getaway soon don’t forget to check out this travel spot on the blog with some of our favorite trips!

What I Use To Pack

Start with the basics- a good carry on, a versatile personal bag, and some organized space savers. When packing I swear by packing cubes. If you haven’t tried them before, I’d encourage you to give them a shot! While this set is more expensive than others, I can speak to the quality and durability of these. They last forever, I love that they have handles and I love even more that they have a separate zipper department on the back of each. It’s amazing how much more I can fit into a small space! Magic, I tell ya! And while I’m not packing for kiddos [thank the Lord, I can barely survive packing for myself], I’ve heard so many moms say they’re great for keeping their kids’ items separated within one or two suitcases! Each kid grabs their cube, and has all their stuff! Another reason to celebrate with a pina.

I also try to make my personal bag a bag that will work for the beach! [And this one has a slit so it can slide right over the handle of your carryon luggage.] I can use it on the plane to keep my travel docs, a book, bathroom items, and a few of my outfits! I’ll talk more about this below!

What I Pack

When you’re packing for a vacation in a carry on, planning is key. You’ll want to make sure that your outfits can coordinate as much as possible to limit the number of shoes you’ll need to bring, as well as being able to throw on that same jacket or pair of jeans more than once. Try not to let yourself fall for the “oh maybe just one more” moments. You know exactly what I’m talking about- at the last minute you start throwing in that dress you haven’t worn in three years, or an extra pair of shoes, JUST in case. I try to bring one extra outfit in case something happens to one of the other outfits, or ya know, I’m just not feeling pink that night. Here’s an example of what I was able to fit into this carry-on:

  • 5 Dresses / Jumpsuits
  • 5 Tops [okay, maybe I allowed a few of those “oh maybe just one more” moments]
  • White Denim Jeans
  • Denim Jeans
  • Jean Shorts
  • Sandals
  • Wedges
  • 2 Reversible Swimsuits [I went with this one and this one!]
  • 2 Coverups [I love finding ones that can double as cute outfits as well – shown below!]
  • Pajamas
  • Toiletry Items
  • Bras/Underwear — don’t forget a strapless bra! This is my tried and true favorite strapless!
  • Jewelry

Here are a few of the items I just got in to pack for St Kitts in case you’re looking for some vacay looks:

Reformation Kaila Wrap Style Jersey Dress  [true to size, wearing in small] // Mavi Jeans ‘Samantha’ Denim Jacket  [size up if in between, wearing in small] // Treasure & Bond Penelope Espadrille Sandal [true to size] Tommy Bahama Cover Up Dress [true to size, wearing in small – this is a great example of a coverup you can wear around the pool OR out to dinner at night]// Treasure & Bond Penelope Espadrille Sandal [true to size]Tommy Bahama Diamond Ikat Ruffle Cover-Up Dress [true to size, wearing in XS] Again, another cover-up/dress that works double duty!//  Treasure & Bond Penelope Espadrille Sandal Bar Iii Floral Printed Mock-Neck Mini Dress [true to size, wearing in small]// Treasure & Bond Penelope Espadrille Sandal CeCe Smocked Off the Shoulder Blouse [true to size] //Kut from the Kloth jeans [true to size] Caslon® Rounded V-Neck Tee [size down if in between] // KUT from the Kloth Gidget Denim Shorts [true to size] // Kut from the Kloth White Jeans [true to size] // Tory Burch Miller Flip Flop [size up .5]

What I Wear On The Plane

For my travel outfit, I don’t just like to be comfortable, I also want what I’m wearing to be versatile. Whether it’s wearing a jean jacket that I can then throw on every evening, or re-wearing a comfy travel dress as a coverup on the trip, it’s less items that I need to pack in my carryon!

How I Pack

Personal Bag:

As I mentioned above, I like my personal bag to double as a beach bag. So finding one with a zip closure and some flexibility [and that I won’t mind getting some sunscreen and sand on] is key. However, before I get to the beach, you better believe I’m loading it up with all sorts of things. We’ve all heard the horror stories about people losing their luggage, and while you may not think you’ll lose your carryon luggage, there’s always the possibility that the plane you’re going to be on will end up checking your carryon bag anyways. To prepare for the risk of losing my bag, I keep my toiletry items and a packing cube with two days worth of outfits and a swimsuit in my personal bag. That way, I’m covered for a day[ish] until I can figure out a game plan for new clothes or my luggage is found!

Also, remember! All of your toiletry items will need to be TSA approved since everything is going to be carried on! Depending on where you’re traveling to, you may have a drug store nearby where you could purchase your sunscreen, shampoo, hairspray, etc. when you arrive! I personally love these silicone bags that you can reuse over and over again for travel!

One more thing — I always pack a crossbody bag for vacation as I like to be hands free while we’re gallivanting around town exploring! I throw little things into my crossbody [aka jewelry] and then put the crossbody in my personal bag [is anybody else having flashbacks to those Babushka dolls right now?] Utilize your space is the moral of the story here.

[also hi, my name is Erin and I have a Tory Burch addiction]

Carry On Suitcase:

  • Packing Cubes
    • The majority of what I pack ends up in my carryon suitcase, stuffed into packing cubes! You can honestly fit SO much into a packing cube – you’d be surprised!
    • What I love about these packing cubes verses others that I’ve had is that they have an exterior pocket on each, so you can fit jewelry, bras, socks, underwear, etc in them once you already think you have them packed full! I loved this!

    • Some people do the roll method with their clothing, but I just fold everything flat! I then categorize my clothes into each packing cube [some people put outfits together]. I did the following: tops, dresses/jumpsuits, pants/shorts, swimsuits/coverups/bras/etc.

    • This set has everything from large packing cubes down to really small ones. After loading up the largest, I still had some extra room, so I ended up putting a smaller packing cube inside the larger one to really suck things in! Utilizing all the space!

    • There was one extra small pouch packing cube that I didn’t utilize for packing, but I still pack it to use for wet swimsuits or sunscreens in my beach bag!

  • Swimsuits:
    • You’d be amazed how many reversible swimsuits are out there now! Flip it around, and your’e basically getting two suits in one, which means less to pack!
  • Shoes:

    • I put my shoes in first, and then put the packing cubes in on top/around them!
    • If you’re packing a pair of closed toe shoes, use that space inside of them to stuff things in- socks, underwear, jewelry, etc!
  • Coordinating Colors
    • I mentioned this above, but when looking at your outfits, try to stick to a color scheme that will work with the item(s) you’re going to be wearing over and over. So if you’re planning to wear one pair of sandals, or one clutch, or one jacket, make sure that whatever you’re packing coordinates with that! Otherwise you’ll start throwing in an extra jacket or an extra pair of shoes for that one outfit.

Now that you know how to pack efficiently, the only challenge left is to decide between the beach and the pool!



share this with your best girlfriends:

  1. Carie says:

    We are tracing to Italy in May and I’ve been working on my packing techniques. The personal bag is the key! I love your choice! I am going to check out the packing cubes you posted. Those may be exactly what I’ve been looking for!!! Thank you!!

  2. Linda Serro says:

    Best advice ever! Funny thing is, I live in SW Florida and I’m looking forward to going to Colorado in March. However, your ideas would work. The Tommy Bahama dresses are darling and perfect for my normal life here in Florida.

  3. Linda Serro says:

    The Nordstrom site for the suitcase says it must be checked for flights…too big? Please advise.

    • Sarah says:

      The most common airline size requirements are 22x14x9 so this bag is officially 2” too large, but it depends on the airline and frankly your flight crew as to whether those are really enforced. MOST of the time I’ve found them not to be – everyone going through boarding around me has one of the oversized carry-ons. ????

  4. Mireille says:

    Been on the lookout for some joggers and will be getting these later this spring! Great for traveling!

  5. Heather says:

    Great tips. I packed just a carryon and personal item for a 5 week trip to Europe. It can be done and then you never have to worry about lost luggage.

  6. Heather says:

    I was hoping you would publish a blog on this topic – yay! Any advice on must haves for long flights? I’m traveling in the summer and the flight is 25 hrs and 35 hrs for the way home. Thanks!

  7. Lindsay says:

    Please go into more detail on toiletries that you actually packed. I packed everything into carry on’s for a six-day trip, easy enough but the toiletries held me up and we ended up checking all of our luggage for that reason only.

  8. Jill says:

    Erin, this helped me so much! What great advice. I totally suck at packing and I think I can nail it now!

  9. Michele says:

    Great tips! And yes, I agree with the Tory Burch addiction also!! The only point I can’t get on board with would be taking a bag like that black quilted one to the beach or pool ! Or did I just misunderstand. When I’m packing for a beach vacay, I just put my Lily Pulitzer beach tote flat on the bottom of the suitcase, practically takes up no room!

  10. Tammy says:

    I wish I was traveling somewhere with warm tropical weather but I will be next month. Everytime I travel I travel light. Couple of dresses, romper, jumpsuit, bikinis, heels, wedges optional and Jean jacket, jeans and sneakers I wear while flying. TSA is horror show.

  11. Michelle says:

    Perfect timing as.I just planned a long weekend in Phoenix with my bestie for February so quick and easy carryon it is! Thanks!

  12. Danielle Patrick says:

    I found these Calpak suitcases at tjmaxx for $60! Cute bright colors too! Love them

  13. Dalit says:

    I’m heading to Spain in May and I think I will be packing Everything on this list. But first…..must buy the pieces. Thank you!!

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