I Packed These 8 Essential Items for a 2-Week Vacation in Italy

For me, the utmost indulgence is not a gooey chocolate lava cake or a buttery Bottega Veneta leather purse (although the two are incredibly gratifying and clearly I wouldn’t pass up either). The highest form of indulgence is an exhilarating, relaxing, and recharging trip to beautiful Italy. I had the great fortune to seriously induuulge this month with a two-week stint in Venice and Tuscany—with hubby and baby by my side (the best!) and a suitcase full of sartorial gems to boot.

Italy is still super pleasant at this time of the year, and whether you’re headed to the cities, the coast, or the countryside, there are certain essential items I would unquestionably recommend packing. From the basics (tank tops and tees) to the comfortable shoes you don’t want to leave without and the chicest dresses to wear from day to night, scroll below to see everything I recommend packing to make your vacanza as comfortable and stylish as possible.

Comfortable Shoes

No matter where you go in Italy, you're sure to be walking substantially—whether it's the hilly streets of Positano or the cobbled stone streets of Rome, you'll want shoes that are comfortable with a capital C. I recommend a pair of trending Tevas (you could walk for miles in them without not a blister in sight), Birkenstocks, or cushy-soled sandals, as well as a chic pair of loafers (to fit right in with the local Italians), a pair of white sneakers that you can wear with everything, and an evening shoe such as espadrille wedges or comfortable low block heels that you can wear for dinner and long evening strolls.

Versatile Jumpsuit

A chic jumpsuit is a mainstay on my packing list (no matter where I'm traveling). It's easy to dress up or down (just add heels and accessories) and proves to be a fail-safe, trusty option when you want something to throw on and go. 

Essential Tops

A white tank top and a black or white tee are a must to mix and match with shorts, skirts, and jeans. In addition, a breezy peasant blouse and casual white button-down are always convenient to have on hand.

City Shorts

As an alternative to denim shorts and jeans, I love a pair of shorts that err on the sophisticated side—especially when visiting chic Italian cities. A high-waisted beige pair a little longer in length looks chic, crisp, and clean when paired with a white tank or blouse.

Midi Skirt

As well as shorts, a versatile midi skirt is another must-have that will take you easily from day to night in style. Opt for a silky slip skirt or a floral number that you can mix and match with your tops or sweaters once it gets cooler. 

Easy, Breezy Dresses

Dresses definitely made up the bulk of my Italian wardrobe—I armed myself with a mix of breezy floral frocks to keep cool during the day, some lightweight dresses that I wore in the Italian countryside, and slip dresses for the evening.


If you'll be basking in the sun by a pool, you'll need a chic bikini and one-piece. I love the glamorous, and vintage feel of a bikini or one-piece that's belted at the waist.


As the temps start to slowly cool, you'll want to be armed with some warmer layers—especially for breezy evenings eating alfresco. A lightweight cardigan, a linen blazer, and a leather jacket will have you covered for all events.


A few bold accessories add the perfect finishing touch to any outfit. Opt for statement gold necklaces and hoop earrings that you can wear from day to night. A chic straw hat, silk scarf, and shades will add a cool-girl touch to your look.

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