We’re only five days away from leaving for Brazil, and I can’t wait to get going – especially since our area just had its first snowfall of the season, with about 15 cm of snow on the ground! I’m eagerly awaiting to sit on the beach in the sun and sipping a caipirinha, but that also means it’s time to pack my backpack and my personal item again.

In another video, I shared the best way to repack my belongings for a long flight to ensure a comfortable trip. I explained which items belong in my personal item and which belong in my backpack. This strategy helps me stay organized and have everything I need handy during the flight, and I use this method to keep my tech gadgets and toiletries handy at airport security.

After I released that video, I received many questions about the bag I was using. So, I decided to take the opportunity to share some insight on bags for personal items and which ones I like to use the most.

Eagle Creek Packable Tote/Pack

This was the first bag I used religiously as my personal item. The Eagle Creek Packable Tote/Pack was an ideal for me because I could use it as both a tote and a backpack. It was very thin and packed up small when I did not need it, it was just the right size for a personal item. It had a zipper on the top, so I could put all my stuff in it, zip it up and keep everything secure.

After I used it regularly for five years, it eventually broke and had a few holes in it, so I retired it with a heavy heart.

At the time, I was still traveling with a MacBook Pro, which had a very secure case, so I could transport it in a thin personal item bag without any problems. However, when I started using an iPad Pro as my primary device, I had to be extra careful because these devices are more prone to bending if they are not protected.

So, I switched to a different bag for my personal item to make sure it stayed secure.

Eagle Creek Wayfarer Messenger Bag

I started using the Wayfarer messenger bag from Eagle Creek. It has a separate padded compartment that fits my 11-inch iPad Pro and iPad Mini perfectly. It also has a large compartment with interior sleeves and a zippered pocket, a front pocket for small items, a flat pocket on the back to keep important items close to your body, and a bottle holder (which is genius on a messenger bag, if you ask me!).

Although the bag was great, I had two issues with it: first, it was not very comfortable to carry my two iPads in it as it got too heavy; and second, it was a crossbody bag, which meant it was not very comfortable to carry with my backpack on long trips.

Meanwhile, I bought a sturdy case for my iPad and I carry it in my main backpack, so I no longer had to carry both iPads in my personal item. However, the padded compartment of my bag was quite thick and took up a lot of space. That’s why I decided to change the bag, and as you can imagine, it was not hard to convince me to buy a new bag.

Bellroy Venture Sling

Despite my reluctance to wear a sling bag due to being left-handed and not being too excited to wear a “fanny pack”, I had my eye on one particular bag for a long time. After hearing many positive reviews about it being the best travel bag, I decided to give it a try. I was hoping that if I wore it tighter in the front with my backpack, it would not be too much of an inconvenience.

Overall, I am pleased with the Bellroy Venture Sling Bag (9 liter version). The color is gorgeous, and the internal organization is brilliant – with many compartments. The eyeglass compartment at the top is especially clever, as it keeps my glasses from getting crushed at the bottom of the bag.

Despite the attractive design, the bag has a major drawback that I cannot ignore: The buckles on the sides open easily, and the bag does not feel secure enough to keep valuables and a passport safe. I thought about resolving the problem with superglue, but given the high price of the bag, I would rather not make any compromises. In the end, I would not feel safe traveling with this bag. Therefore, I returned it.

Peak Design Packable Tote

But the question remains: Which bag should I take with me on my upcoming trip as a personal item?

Fortunately, I have found a fantastic substitute.

My first favorite, the Eagle Creak Tote/Pack, inspired me because it’s so thin, and I loved the zippered closure to keep my stuff secure. I found a very similar replacement – the Peak Design Packable Tote.

It’s a big bucket out of a thin fabric, and it folds up into an interior compartment when needed. I especially like it because it has a zipper and only one handle, which is covered with something that makes it less slippery. Therefore, when I carry it over my shoulder, it does not slip off as easily, which was the case with the Eagle Creek bag.

I no longer worry about my iPad because I bought a hard case for it, and I am convinced that my iPad is well protected.

Alpaka Zip Pouch Max

Since there is not much organization in my bag, I will combine it with an Alpaca Zip Pouch Max from Alpaca Gear that I received for testing. I have been using it for a few weeks now, and it’s very practical and has a slim profile. It has a zippered compartment on the front, one on the back, and another large zippered compartment, so I can keep all the things I want with me organized. If someone complains about carrying two bags, I can just put it into the Peak Design Tote.

I am excited to use this combination for my next trip.

Finding the best personal item bag?

Honestly, I am still searching for the perfect bag for my personal item: One that can be worn either crossbody or close to the body if needed, has a bottle holder, is lightweight and thin, and has all the other desired features. I can dream, but for now, I am happy with the combination I have found, and I am ready to leave winter behind and return to summer.