Favorite Things I Packed for Italy Trip + Things I Wish I’d Brought

It has rained at least one day on each of my trips to Italy, so this time, I prepared by ordering a compact umbrella that came with a small, packable case.

It was easy to fit in my purse or backpack during our outings, and I whipped it out more than once. It wasn’t the highest quality, but it was convenient and portable.

We’ve all asked a stranger to take our photo on vacation, and when we get the phone back, it’s fuzzy and there’s a thumb in the corner of the frame.

That’s why I bring a slim and easy-to-pack phone tripod with me on every trip. It fits in most small totes and can be propped up in seconds. The one I have also operates as a selfie stick.

Just set your phone on self-timer or download a remote shooting app, and you’re ready for finger-free group photos. This has also come in handy many times while I was solo traveling.

Getting through airports, hopping on and off trains, and dragging my stuff across bumpy cobblestone walkways is the price I pay to visit such a beautiful destination.

One way I (literally) take some of the weight off my shoulders when moving from place to place is by using a backpack with a flap on the back that slips over the handle of my luggage.

I actually have more than one backpack with this feature now because it’s that much of a gamechanger for traveling. I regularly rotate between my Beis backpack and Portland Gear version.

I love this Tessan adapter from Amazon because I can plug in multiple devices at once.

It has four outlets, two USB-A ports, and one USB-C port, so I know I can rely on it for charging my phone, plugging in my hair tools, and anything else I might need.

Plus, the plug folds down, making it even easier to pack. In addition to my universal adapter, I have this specific converter for several regions of the world.

When wandering through major tourist cities, I always carry an over-the-shoulder belt bag to keep my money, passport, phone, and cards safe and within arm’s reach.

These bags are also practical for sightseeing. For instance, I went on a three-hour walking tour of St. Mark’s Basilica in Venice, and wanted to participate without worrying about carrying or keeping track of my things.

Being hands-free for big activities like this always makes the experience more convenient and enjoyable.

Planning outfits for a trip is one of my favorite parts of travel prep. I love to dress on theme and get a snapshot of the moment.

However, on my last trip, I realized that packing items I’ll only wear once for a couple of hours just isn’t worth the hassle. For example, I packed a long red gown to wear just in case we went to a fancy dinner. And, yes, it did sit folded in my suitcase for two weeks.

Next time, I’ll bring more versatile items that I can mix and match for various occasions throughout the trip.

Don’t ask me why I packed two pairs of white sneakers. It seems silly now, but my logic was that one pair was for active outings and one was for more fashionable outfits.

However, this was unnecessary, and I could have just brought one pair and been fine. In fact, I’d avoid white shoes altogether in the future, as they can get dirty and matted on the cobblestone streets.