Brushing Off The Cobwebs: Packing For Two Weeks In Italy In A Carry-On (Part 1)

It’s hard to believe it was over six months ago that I wrote about attempting to pack for a two-week trip to Italy in a carry-on. I realize I haven’t followed up on how the strategy worked out, or anything about the trip in general. Much like other highly-anticipated events in my life, after it was over I felt a bit sad and withdrew from the whole thing for a while. Because although it was an amazing experience, it was over far too quickly compared to the amount of time daydreaming, researching and planning.

It took some time to decompress after getting home and getting back into the swing of reality again. After a month I found the energy to sort through all of the photos captured on my phone, Matt’s phone and the camera (somewhere around 2,500 in total). A couple months later I made a photo book as a keepsake (call me old-fashioned, but I think some things still deserve paper and ink). As the epically-brutal winter wears on this year, my mind has started wandering back it Italy more and more often in the last month or two.

So now seems as good a time as any to delve back into my memory and start telling you about the highlights (and some low points) of the trip over my next few posts. But first, I think I’ll start with what really ended up getting packed. When I first mentioned the trip, I had already resolved to “pack light” knowing it would be difficult to navigate 4 cities over two weeks. However, with temperatures ranging from the 50s to high 70s and imminent threat of rain I realized it would be no easy task. In subsequent posts, I struggled over options and possibilities related to rain gear and footwear. In the interest of not making this a 10-page long post, let’s begin with that piece.

I ended up bringing five pairs of shoes (yes, five).

Screen Shot 2013-08-20 at 2.10.52 PMBirkenstock Gizeh Birko-Flor Thong Sandal in Licorice: Before Italy I never thought I would own Birkenstocks; I’ve got to hand it to the countless posts in online forums pointing the way to these sandals though. Since this style is a synthetic material they didn’t require the same break-in period as leather thong sandals. I walked many comfortable miles over cobblestone streets and even hiked steep trails in Cinque Terre in these and would recommend them to others who will be spending lots of time on their feet.

Screen Shot 2014-03-17 at 4.15.00 PMJ.Crew Cece Suede Ballet Flats in Rosewood (no longer available): if you follow lovesthat you know I have these flats in 4 colors. They take a bit of work to break in but once you do they’re fantastic. The design is simple and chic and the colors while classic aren’t flat. The one downside is that suede get easily dirty and ruined (and are obviously not rain-friendly), though proper care and cleaning can keep them in tip-top shape.

_7801557.jpgDV by Dolce Vita “Molly” Tasseled Smoking Slipper (no longer available): these were not the most comfortable of my options, but helped to have in the rotation when my feet hurt from wearing a different pair of shoes for too long/often. To an extent I chose vanity over comfort; I’m sure I could have had a bit less fatigue if I’d chosen to bring sensible sneakers, but that just doesn’t jive with my style. Instead I chose the most versatile footwear possible for styling but that I knew wouldn’t completely kill my feet. These slippers have no arch support, so I brought along and added some inserts that helped a bit.

Simple black rubber flip flops – not a necessity, but they took up very little space and gave me peace of mind knowing I had an extra option that was waterproof. To be honest I don’t remember wearing these which makes me question whether I actually brought them, but I think I did on both fronts.


Saving the best for last, the final pair which I wore for every leg of travel were these Prada boots. Remember how I thought I would be tromping around Italy in my Frye “Veronica” Back Zip Short Boots? Well it didn’t quite work that way. Since they zip in the back, even after a painful break-in period (I’m talking stuffing napkins in my heel to prevent further rubbing while limping around work), they were still not (and still aren’t) comfortable enough for long periods of walking. I was about 2 weeks away from leaving when I came to grips with the fact that these simply weren’t going to work, and I was starting to panic.

That’s when my friend Amy turned into my fairy godmother, telling me she has a pair of incredibly comfortable flat boots with rubber soles that would be perfect for my trip. She was in town for work from Chicago and we were discussing this over dinner; the following week she shipped me her boots which fit like a glove and were every bit as comfortable as she claimed. I wore them almost exclusively the first half of the trip as it rained every day we were in Venice and intermittently in Cinque Terre and Florence (it was even worse than I had feared). Thinking back I honestly don’t know what I would have done if I hadn’t had those boots. Limped a lot throughout the trip, probably.

Thankfully my actual clothing selection and packing went a lot more smoothly and for the most part worked out well. More on that next time.

— Maureen


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