How to Pack for a Trip to Florida in Just Two Carry-On’s

I was not the first person to go to Florida for a long weekend this year. In fact, it’s entirely possible I was the millionth. But with Spring nearly upon us and a lot more people gearing up to escape to the sunniest corner of our great nation, I thought it would be topical to discuss how I prepared for my own recent beach getaway.

For my birthday at the end of February my family invited me and my boyfriend to a long weekend at my uncle’s condo on Singer Island, which is a barrier island off the coast of West Palm Beach. He has a dazzling four-bedroom, five-bathroom unit facing the Atlantic. I’ll admit – it was a blessing to have been invited to stay at such a gorgeous spot in the world!

While the lodging and food were mostly paid for that weekend (thanks family!), my boyfriend and I still covered the cost of our plane tickets. West Palm Beach is a town of old money, and the airfare prices sure reflect that! My boyfriend and my tickets were both over $400 each from New York City, given we chose to fly during peak times. (Note: you can find better deals to West Palm Beach if you purchase in advance or travel during off-peak hours.) Although both my boyfriend and I have the ability to check one free bag each (thanks Citi AAdvantage card!), we decided this trip that we wanted to prioritize maxing out our time in the sun by only taking two carry-ons each.

But how to do you pack a carry-on for a beach vacation when you can barely remember what 80 degrees Fahrenheit feels like!? Winter in New York had been brutal this year! Add to that the challenge of balancing bumming around the beach with eating at posh restaurants.

I was somewhat perplexed with how to pack for this trip.  Here is what I knew I needed:

  1. Travel outfit – this would need to include long pants and a sweater or sweatshirt since it was under 20 degrees in New York
  2. Boating/Lunch outfit – something that I would be okay to get sunscreen and ocean water on, but would still look nice enough to be served at a trendy dock-side eatery
  3. (3) Nice dinner outfits – all fairly dressy, since my uncle is a foodie and prefers to dine at high-end restaurants
  4. Activity outfit – on trips like this, you never really know what to expect with the weather, and on a rainy day we received a private tour of the nation’s leading sea turtle hospital ( from its CEO, so we needed to dress appropriately for the chilly rain as well as the formal tour
  5. Beach garb – two swimsuits, beach cover-up, flip-flops, etc.
  6. Workout clothes – two sessions worth of workout clothes for morning exercises
  7. Pajamas – When I’m with family I usually prefer to bring loungewear so I can feel comfortable during late-night chats or while watching movies
Family dressed up for my birthday dinner!

Family photo before my birthday dinner – all dressed up!

So here’s how I tackled it…

In flight strategy = LAYERS:

  • Green jeans w/ brown leather belt
  • Light-weight mixed material crochet sweater with black cami
  • Beige canvas military jacket
  • Brown sneakers and grey socks (I normally NEVER wear sneakers with jeans, but since sneakers are featured in all of the fashion magazines lately, I thought I’d try to pull off the look with a pair of neutral-colored kicks. This would allow me to be able to work out at the gym in the mornings.)
  • Wool winter coat
  • Undergarments (of course)

Clothes and shoes I packed:

  • (2) bikinis
  • (1) swimshirt for watersports
  • (1) terrycloth beach cover-up
  • (1) waterproof workout shorts
  • (2) workout capris, used one the whole trip for PJ bottoms
  • (3) workout shirts, used one the whole trip as a PJ shirt
  • (2) pairs workout socks
  • Lightweight solid white zipup sweatshirt
  • (2) chino shorts – cobalt and black
  • (3) nice colorful sleeveless tops in silky, breathable fabrics
  • (1) deep blue cropped cotton cardigan
  • (2) day or night sundresses
  • (2) pairs regular socks
  • (1) black flip-flops
  • (1) brown leather strappy sandals
  • (1) black high-heeled sandals
  • (1) strapless bra
  • (6) pairs assorted underwear
  • (1) black belt

Other items I packed:

  • Small bag of matching jewelry
  • Makeup bag with cosmetics for (1) evening skin look, lipbalm with SPF, (1) day eye look, (1) evening eye look, and (5) assorted lipsticks and glosses
  • Toiletries bag inclusive of separate stashes:
    • Travel-size shower items and razor
    • Travel-size face wash, makeup remover, and skincare
    • Toothbrush and travel toothpaste
    • Travel-size body lotion
    • Nail polish to match my manicure in case of chips
    • Travel-size sunscreen
    • Travel-size perfume and deodorant
    • Cotton balls/Qtips
    • Travel size hair styling products (I brought one ounce containers of argon oil, anti-frizz hair milk, blow-dry protector, and flat iron heat protector, which would normally seem excessive. However these items were essential since my hair would become untamably frizzy each day in the Florida heat.)
  • Laptop, phone, headphones, and chargers
  • Magazines and books for the plane and pool
  • (2) pairs of sunglasses
  • Digital camera
  • Large collapsible beach bag
  • Small black leather evening purse
  • Medium-size brown leather day purse
  • Eyemask

As you can see, I was able to fit a lot into only two carry-ons. I’ve found that if you buy the right luggage and supplies to help you reduce bulk, you can pack a lot more than you think! My two biggest packing take-aways from this trip are:

  • For a long weekend trip, try purchasing several one-ounce travel sized canisters at the Container Store. Typically travel size items sold in stores are 3oz, so the smaller size reduces the mass and weight of your toiletries bag significantly. (As a note, you may need to buy a full-sized sunscreen once you arrive if you’re as fair-skinned as I am!)
Travel Size Containers

1-ounce or less travel size canisters from the Container Store, TravelGuard razor container, Travalo refillable perfume sprayer

  • Bring light layers. It helps to be able to mix and match your outfits, especially so you can stay warm at night after changing out of your beach clothes! On my trip the temperatures sometimes dropped at night to the upper 50’s, so I was very thankful that I brought different layering options!

    Shelling on the Beach

    Shelling during low tide on a rainy day

The above is an all-inclusive overview of the packing strategy and secrets that really worked for me. The biggest win was that even with bringing so many outfit options, my carry-on roller duffle still fit into American Airline’s baggage sizers for both flights! That said, I know many people may have some more tips and tricks to add. Let me know if I missed anything!


Sheer bliss!

Sheer bliss!


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