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Italy & Mediterranean Packing List: Carry-Ons, Cobblestone Shoes & Church-Ready Layers

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Rome's St. Peter's and Florence's Duomo can turn you away at the door for bare shoulders or knees, so the easiest fix is a lightweight wrap that lives in your day bag all trip. This Italy and Mediterranean shoulder-season packing list covers carry-on...
 
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The wraparound zipper is the reason this is my pick for Italy: it holds 5-8 outfits closed and expands 2.25 inches on the way home when the ceramics and olive oil come along. Wheels spin easily on station platforms, and it still fits the overhead bin...
Away The Carry-On Flex in Navy Blue
 
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A zip top is exactly what you want in a crowded piazza or on the Metro in Rome, because nothing can slip out of the opening. It fits a phone, a small wallet and a pouch, and the leather softens into a nice patina over a week of walking.
Madewell The Zip-Top Transport Crossbody
 
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This is the church-cover-up piece. Fold it into your day bag in the morning, then drape it over your shoulders at the basilica door and nobody blinks. It also doubles as a warm layer on an evening ferry deck when the Mediterranean air cools off in Oc...
Anthropologie By Anthropologie Asymmetric Wrap Shawl
 
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Madewell's Cloudlift Lite padding makes a real difference on the second hour of uneven stone. The elastic strap keeps the heel put, and the square toe looks polished enough for dinner. Madewell says the leather stretches with wear, so consider going ...
Madewell The Greta Mary Jane Flat
 
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The trolley pass-through slides over a suitcase handle, which makes platform transfers so much easier. The separate bottom compartment keeps shoes away from clean clothes, and at 42L it works as a carry-on on its own for a four-day city weekend.
Béis The Weekender in Black
 
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Visible Air cushioning is a good match for cobblestone, since the heel absorbs the pounding that flat canvas shoes pass straight to your knees. Nike notes they fit small, so order a half size up, and break them in at home before you land in Italy.
Nike Air Max 90 Women's Shoes
 
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These Featherweight Stretch pants shrug off wrinkles after a flight and still look dressy at an aperitivo. The ankle length shows off your shoes and keeps hems off wet streets, and the pockets are deep enough for a train ticket. They pair with every ...
Athleta Brooklyn Mid Rise Ankle Pant
 
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This is the anti-theft pick for crowded spots like the Trevi Fountain or a Naples train. It has a hidden back pocket for a passport and theft-deterrent zipper pullers, and it cinches slim or expands to hold a camera. Wear it in front of you, not behi...
Béis The Pro Travel Sling in Black
 
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A wool scarf earns its space in October when Venice and Florence mornings run cold, then covers your shoulders at the next church. Because it is lightweight, it folds flat in a pocket, and the plaid hides small travel smudges between laundry days.
Anthropologie Maeve Lightweight Plaid Wool Scarf
 
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The front laptop pocket lets you grab documents and a tablet without unpacking in the security line. It weighs about 8 pounds and has a tough polycarbonate shell with 360-degree wheels. Pack it to fit the overhead rack or the luggage area at the end ...
Calpak Ambeur Front Pocket Carry-On Luggage
 
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Loafers are the easy way to look local in Italy, and these have a rounded square toe that handles walking all day better than a pointed one. Leather lining means they mold to your foot, and the rubber sole gives enough grip on polished marble steps.
Madewell The Ashley Ruched Loafer
 
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At under 40 dollars full price, this is the bag for the day you do not want to worry about a nicer one. It fits a phone, cards and lip balm, and the 40-inch adjustable strap lets you wear it across your body, which is the safer way to carry anything ...
Aerie OFFLINE By Aerie Makin' Moves Crossbody Bag
 
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Linen breathes during warm Sicilian afternoons, and the button front gives you a sleeve to cover your shoulders at a church. It is machine washable, which matters when you are rinsing clothes in a hotel sink. Try it over a tank for the full church-fr...
Madewell Linen-Blend Crewneck Cardigan
 
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This is a personal item that slips over your suitcase handle with its trolley sleeve. A top zipper keeps things closed in crowds, and the padded pocket holds a 16-inch laptop if you travel for work. For Italy it carries a water bottle, a scarf and a ...
Away The Everywhere Tote in Navy Blue
 
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The triangle shape stays in place on your shoulders better than a rectangle scarf, so you are not constantly readjusting while you look at frescoes. The open pointelle knit is light enough for spring and just warm enough for an October evening on a t...
Anthropologie By Anthropologie Pointelle Triangle Wrap Scarf
 
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It has a dedicated shoe compartment, which is useful when you pack both sneakers and loafers for different days. The trolley sleeve means it rides on your rolling bag, and with nine pockets it is easy to find the train tickets. It suits a weekend sid...
Calpak Luka Duffel in Oatmeal
 
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The leather upper resists scuffs and creasing, and the foam midsole with a wedge insert is comfortable for long city days. A gum sole looks more European than bright running shoes, and it goes with jeans, dresses and trousers. Nike recommends a half ...
Nike Cortez Women's Shoes
 
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Spring showers in Rome and fall drizzle in Lisbon are why I like a water-resistant layer that stuffs into a bag. The stowable hood saves you from carrying an umbrella, and the zip pockets keep your phone safe on a crowded tram. It looks neat over a d...
Athleta Dash Jacket
 
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With a trolley pass-through, hidden phone pocket and a water bottle pocket, this works as the personal item on the plane and the daytime bag in the city. It stands up on its own, so you can find your passport quickly at a hotel desk or check-in count...
Béis The Commuter Tote in Black
 
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Wear it across your body for sightseeing and it keeps your phone and cards in front of you with hidden exterior pockets. It weighs only half a pound and is water-resistant, which helps in a sudden rain. It also counts as a personal item on most airli...
Calpak Luka Belt Bag in Glazed Black