[UPDATED August 2026] I’m a carry-on traveler. I rarely check luggage, even for international trips. For nine days in Italy in a carry-on, I traveled with a small roller bag and a backpack, which is my usual travel combination for trips ranging from a weekend to about two weeks.

Packing light is admittedly easier in summer when bulky sweaters and jackets aren’t needed. It’s Italy where the shopping is phenomenal, so leave room in an expandable carry-on roller. 

Here’s how I packed for nine days in Italy in a carry-on. I’m also including what goes in my backpack, and the packing tips helping me stay organized.

Choosing a Carry-On, Backpack and Crossbody Bag

My Lo & Sons Waverley 2 purse has been a travel staple since I took it to Switzerland and Paris in 2019. It can be worn four ways, but I typically use it as a crossbody bag. In Rome, where travelers need to be aware of pickpockets, I shortened the strap so the bag sat closer to my chest instead of against my hip.

It also fits inside my Lo & Sons Hanover Deluxe 2 backpack when needed. The purse and backpack have traveled with me from Zurich to Santiago and on many trips in between. Hanover Deluxe is no longer available, but the Melrose is a great option with a detachable crossbody pouch, or the Rowledge 2 laptop backpack.

I always bring a lightweight packable backpack, too. For years, my go-to is Matador Equipment’s packable backpacks. In August 2026, Matador revamped all of their bags. The 18L Packable Backpack is my favorite. It works for day trips, hikes and beach outings, and it can become an extra bag if needed for the trip home.

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What I Pack in My Personal-Item Backpack

My backpack holds electronics, travel documents, medications, jewelry, and other things I don’t want to put in my roller bag in case it has to be checked.

In the padded compartment closest to my back, I packed my iPad, keyboard and charging cable. Switching from a laptop and small iPad to one larger iPad with keyboard saves valuable space and weight.

For this trip I also packed a slim wallet, doubling as a clutch for evenings. Something like the Slimvelope Clutch Wallet is perfect for ID, credit card, and to stash some euros, including coins that you need for public toilets in Europe.

Cash Tips: While Italy and other European countries are very card-friendly, I like having some local currency for small purchases and emergencies. Instead of carrying all your cash in one place, divide it between secure locations. If you use an ATM, choose one affiliated with a bank. Decline dynamic currency conversion if you’re offered the option to be charged in U.S. dollars. Always purchase in local currency, even for hotels.

In the main compartment I use a layering system. Toiletries kit goes in first. Clutch wallet with bulk of local currency and jewelry pouch slide in next to it on the bottom. Tech bag, jacket, or anything else I might need enroute goes on top.

Summer and Early Fall Tip: With scorching temperatures, and since a lot of places in Italy, and across Europe, don’t have air conditioning, it’s a great idea to travel with compact personal fan. A couple of my favorites are: 3-in-1 portable fan with power bank, slim portable fan, and the rectangle portable fan I took on this trip.

Electronics and European Plugs

Italy uses European-style plugs, so I packed plug adapters along with a universal converter. My phone and iPad only needed an adapter because their chargers accept dual voltage.

Hair dryers, curling irons and straighteners are, of course, another story. I travel with a dual voltage curling iron/straightener combo for touch ups. I love getting blowouts in local salons while traveling. It’s a slice of everyday life and is ultimately a time saver for me.

One of my best packing tricks is keeping a dedicated travel tech bag ready to go. Mine holds:

• A portable charger and cable
• Phone charging cables
• A dual USB plug
• A reusable cable tie
• A car charger
• A small fan (if traveling in summer or early fall)

Keeping everything in one pouch makes it easier to find a cable without excavating the entire backpack.

Toiletries and In-Flight Essentials

My Eagle Creek Pack-It toiletry kit holds everything from my toothbrush and deodorant to makeup. I keep smaller essentials such as bandages, an eye mask, earplugs, ponytail holders and pain relievers in the upper pockets.

For shampoo and conditioner, I use Matador FlatPak Toiletry Bottles in my quart-size liquids bag. The refillable containers take up less space than traditional bottles.

The easy-to-reach pocket of my backpack holds tissues, hand sanitizer, snacks, lip balm, lotion, Airpods, charging cord, and other small travel essentials like peppermints and Ricola drops, which are helpful during take-off and landing. 

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Tech Tip: Created a “travel tech bag.” I did this several years ago and it goes on every trip. This small pouch holds a portable charger and cable, 2 phone charging cables, car cigarette lighter charger (when traveling internationally), and double USB plug.

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How I Organize My Carry-On

My carry-on roller is highly organized because every inch counts. Before packing, I lay out the clothes I’m considering and remove at least 10 percent. There are always a few “just in case” pieces trying to sneak aboard.

Clothes Tip: Less is more! Lay out clothes/outfits you’re thinking of taking then take out at least 10%, especially if you’re heading somewhere like Italy where you’ll likely shop.

Build a Mix-and-Match Wardrobe

I start by thinking through each day’s activities. My travel wardrobe is typically built around black, white and gray, with colorful scarves or jewelry as accents. A neutral palette makes it easier to mix and match pieces and repeat outfits without looking like you did.

Choose lightweight fabrics that breathe, resist wrinkles and dry quickly. Italy can be very hot in summer, but you may still need to cover your shoulders and knees when entering some churches.

Use Packing Cubes

Packing cubes keep clothes organized and help reduce wrinkles. I use two compression cubes, a double-sided packing cube and a smaller cube for accessories and delicates. My long-time favorites are Eagle Creek Packing Cubes, and I especially like their compression ones.

During the trip, I put dirty clothes in a compression cube or on the opposite side of a double-sided cube. It keeps clean and worn clothing separated without requiring an extra laundry bag.

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Use Shoe Covers

Shoes can take up more room than anything else in a carry-on. I keep them together in one compartment and place sandals and other pairs in shoe covers. A designated shoe cover also works well for a hairbrush or styling tools.

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My 9-Day Italy Packing List

Here’s what I packed for my summer trip:

Shoes

I took six pairs, including the running shoes I wore on the plane. That is more than most carry-on travelers need, but the trip included city sightseeing, workouts, evenings out, a wine tour and a day along the coast.

Whatever number you choose, take at least two comfortable pairs that you have already broken in. Alternating shoes can help when you’re spending long days walking over the cobblestones and uneven streets of Florence and Rome.

Clothing

• Three pairs of black capri pants
• One pair of lightweight black pants
• One black skort
• Two black maxi dresses
• One dress for a wine-tasting tour
• Three dressier tops
• Four T-shirts
• Three workout outfits
• One pair of pajamas
• Four pairs of socks
• Nine pairs of underwear
• Three bras
• Three scarves

I also packed a foldable hat, packable backpack, hairbrush and a few pieces of jewelry.

The scarves were especially useful. They added color to simple outfits and provided extra coverage when visiting churches and cathedrals.

I brought Woolite packets and laundry sheets so I could wash socks, underwear and other small items in the sink. A little laundry along the way can eliminate several days’ worth of clothing.

What I Packed but Never Wore

Despite my efforts to pare down, I didn’t wear a black top, white jeans, black shorts, a sleeveless black dress, or one of my scarves.

Even expert packers like me still pack more than we need. On my next trip, those unused pieces are the first to stay home.

Final Tips for Packing for Italy

Packing for nine days in Italy in a carry-on is completely doable, especially during the warmer months. Build outfits around a coordinated color palette, use packing cubes, take comfortable shoes and leave room for something special you find along the way.

Most importantly, check the baggage size and weight rules for every airline on your itinerary. A bag that qualifies as a carry-on for one carrier may be too large or heavy for another, especially on flights within Europe.

I managed to fit everything into a roller bag and backpack, stayed organized throughout the trip and still brought home a few Italian treasures. That counts as packing success in my book.

Here’s where you can find my current two-bag setup for carry-on travel. If heading to Central America, here’s my packing list for 9 days there.