I just got back from Italy and being a pro at procrastination, am doing a trip report instead of unpacking and trip laundry! I never checked the Aeronaut and kept it under seat for most flights, which I can do because I'm short.
Here's a picture of the packed bag along with Lorenzo the silly lion I picked up canal-side in Venice.
On the left a steel PCSB with my in flight necessities. I had an inflatable pillow, Side Effect with passport and wallet, phone (new iPhone 11 with battery life I never had to worry about) paperback book, external battery pack. I usually travel with a Kindle but was in the middle of an excellent book (The Great Believers) and wanted to finish it. Plus I think real books are excellent props when traveling :)
The main compartment has the Aeronaut 30 packing cube backpack in packing cube mode, which held all my clothing and was a great day bag the days I needed a sweater and an umbrella, which was most days.
The Second Aid pouch held my Starbucks Via coffee and immersion heater because being without coffee is a dangerous proposition for me. I only needed the immersion heater in my Venice hotel room. The other places I stayed had kettles.
The wasabi PCBS held my Teva sandals, which I really didn't need but thought I would. Next time I'll travel with lighter slides or flip-flops. I only ever wore them to breakfast in the hotel.
On the right a wasabi clear cube with my medications and toothbrush and a Ziplock bag with toiletries.
On the go most of the time I wore my Side Effect sling bag style, (like how cool people wear fanny packs these days) with the waist strap. This was really helpful as it kept all my necessities right in front of me and always in view. I carried my passport (needed for entrance to the Venice Biennale) and credit cards and cash and phone in it.
I did five flights, three trains, three cities (Genoa, Venice, Rome) and this system worked really well. I'd do it again!
Here's a last pic with Renzo the silly lion who was squished inside for the return flight but didn't complain.
Edit to add my trip all-stars: a long sleeve Smartwool tee that I used as a sweater, Lululemon on the fly pants, iPhone 11 with Sprint international high speed data pass ($25/week and money well spent) and Altra Timp shoes. A note about the Sprint high speed data pass: you're supposed to get a text when you turn on your phone at your destination, but I never did. Luckily I was able to purchase it anyway. I did get a text when the first week was over.