How-to Tuesday: Packing for a 2-week Trip in a Carry-on

Our original plan was to start our honeymoon in the Amalfi Coast and then hit up Tuscany.  However, when I found out we would be landing in Italy the day before Il Palio, I decided to flip it because we couldn’t NOT take advantage of the once in a lifetime opportunity to attend.  Basically, the Palio is an annual horse race in Siena and is a HUGE deal.  The more I read up on it (and the contrada system in Siena), the more excited I became.  When I found out we could attend the contrada dinner the night before the big race, I signed up immediately and prayed our flights would run on schedule.  We were set to land in Florence at 5 PM on Friday, and the dinner started in Siena (an hour and a half away) at around 8:30 that night.  We would be cutting it very close and couldn’t afford to be waiting around at baggage claim.  That meant squeezing 2 weeks worth (16 days, to be exact) of clothing into a single, carry-on bag.  Eek.  It’s tough, but not impossible.  Here’s how I did it:

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  1. Use a duffel.  I went with my trusty Vera Bradley (size: Large) because I knew I could squish those soft sides into any overhead bin.
  2. Choose your shoes wisely.  I decided to pack 2 pairs of nicer “going out” shoes (one wedge, one sandal).  Note: you could totally get by with one pair – even if we went to a nice dinner every single night of the trip, a pair of neutral (read: beige or gold) shoes could go with any dress – black, white, navy, or colorful.  If a dress doesn’t match, don’t pack it.  I also packed 1 pair of flip flops, 1 pair of tennis shoes, and 1 pair of flats.  If you pack one pair of heels, you could get away with two flats, one pair being dressier.  This would be the smarter move because they take up less room…but I don’t always go the smarter route..  I wore Adidas Allstars on the plane since they’re the bulkiest.
  3. Use ziplocks.  Pack all your undergarments and bathing suits in ziplock bags.  It will remove unnecessary air pockets in your bag.  You’ll also be thanking yourself when you don’t have to dig through your bag to find your undies.  One of those ziplocks can also be used later for your dirties.
  4. Romp around.  Summertime clothes may take up less room (tank tops are smaller than sweaters), but I often find I need to pack more of them.  I didn’t want to be wearing the same highly recognizable, bright Lilly Pulitzer top in every photo from my honeymoon.  Separates inherently take up more room.  For every shirt, you also need to have a pair of pants.  One item is always better than two.  Even if you intend to wear that pair of pants multiple times, you’ll still save space if you pack mostly single item outfits.  That means the majority of my clothes were sundresses and rompers.  Rompers are so perfect for the daytime.  They give you the utility of shorts/pants but take up very little room in the suitcase.
  5. Think “transitional”.  Most clothes I brought fell into the “day-to-night” category.  All I had to do was switch to a pair of heels and the outfit became appropriate for a nicer dinner.  I anticipated many of our days would be spent running around until we just fell into dinner without going back to shower and fully change so there was no need to pack 2 outfits for every single day.
  6. Roll your clothes.  I didn’t believe this tip when I first read about it, but it works.  Instead of folding your clothes, roll them.  They take up less room and remain relatively wrinkle-free.

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In case you’re wondering just how much I packed, here’s my full packing list:

  • Bathing Suits (4)
  • Bathing Suit Cover-ups (2)
  • PJs (4 sets)
  • Jeans (1 – just in case there’s a chilly night)
  • Daytime Pieces (2 pairs of denim shorts, 5 tops, 1 maxi skirt)
  • Day-to-Night Outfits (9 – 4 rompers; 5 sundresses, 1 dressy top)
  • Nighttime Dresses (3 – at most we would only do a “fancy” night once in each of the 3 more major cities we visited: Florence, Amalfi, and Rome – the two Tuscan towns we went to would be more low-key)
  • Workout Outfits (2)
  • Undergarments/socks
  • Shoes:
    • Flip Flops (beach)
    • Jack Rogers
    • Gold Wedges
    • Nude Block Heeled Sandals (Could totally sub these for dressy flats to save room, but it was my honeymoon so I wanted to go crazy.  Sue me)
    • Tennis Shoes
  • Clutch (1 – neutral color to match any nighttime outfit)
  • Hats (1 baseball hat – a large floppy beach hat was carried on the plane)

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  • These tips cater to a summertime trip, and I know that wintertime travels are an entirely different nut to crack.  If you’re interested in packing tips for an all carry-on winter trip, let me know!
  • You’ll still need to pack a fewwww bulkier items.  Even if it’s summer and super hot where you’re going, you’ll need to pack some jeans/maxis, longer sleeves.  This is for several reasons:
    • You may have activities that necessitate extra protection.  We’re spending a day butchering and cooking an animal so we need to wear close-toed shoes (as one does in a kitchen) and long pants since we’ll be going in and out of a walk-in refrigerator.
    • If you plan to visit religious sites (like the Duomo, for instance), you’ll need to be covered up for modesty.
    • If you’re like me, you’ll get chilly on the airplane and want the ability to get comfy without anyone potentially seeing up your skirt.  Thankfully, a lot of the layers you wear on the airplane (scarf, cardigan) can totally double as shoulder covers for those cathedrals so you really only have to worry about getting one of those bulky items (a pair of jeans) into your luggage.
  • My packing list does not include those items that I packed in the tote bag that I also carried on (my “personal item”), which included all my toiletries, makeup, jewelry, iPad, chargers, books, camera, and travel journal.  Yes, it’s a solid tote bag that I strategically stuffed a TON into…but that’s for another post.
  • Almost everything I brought could work as either daytime or nighttime outfits.  With flats, my rompers were all great for walking the cobblestone streets of Positano, but when paired with wedges and statement earrings, they were perfect for a romantic cliffside dinner.  While many days still required two outfits (because I would sweat through the first one on a hike), this helped cut down on the volume of outfits a bit and offered me flexibility.