Packing Report, 2025, part 2

In the future I think it would be best to bring just one backpack and use it as my personal item and my day bag.

Welcome home from what sounds like a wonderful trip! I have a few suggestions that may or may not help you, but this is what I basically do and it's been successful, with a few additions to make it consistently work.
I have a 21" wheeled carry-on. I avoid checking it on the way somewhere. I attach a smaller size Portland Gear backpack to the extended handle by its trolley sleeve. It fits snugly, creating a solid "unit" for rolling along. I use a Tom Binh pocket as a crossbody throughout that is just big enough for phone, passport, tiny travel wallet and glasses (and a stretch band style money belt, depending on destination).
Packed flat in the bottom of the wheeled bag:
*Baggalini zip into itself small backpack for hiking days (you might not need that). It can hold my (small aluminum) water bottle, jacket, etc. Super lightweight and washable.
*Synthetic polyester fabric 4" square zippered black museum tote. Unzipped it becomes my day tote for cities, a little nicer look and less bulky than a backpack. It also holds the day's supplies and small purchases ;)
Lastly, consider a fold up duffle for your purchases. Mine is a zippered Eddie Bauer, lays flat and unzips to the size of a typical large gym bag. I only take it if I anticipate shopping a lot! If so, it becomes my carryon for the return home. (I check the 21" with dirty laundry.)
Even if you start filling it during the trip it's not as unwieldily as the juggling you describe.
Technically I don't need the Portland Gear, since I only actually use it on the plane. It just works so well to hold exactly what I need for transit and at night I keep my tablet and etc in it (after experiencing a hotel fire years ago I do this always).
Hope this helps!

I'm glad it all worked out for you.

I'll be honest, I think my BP went up just reading the number of assorted bags you brought and then you purchased more. I'm having trouble wrapping my head around this.

Bon voyage! Thanks for your suggestions. I actually have a folds-into-a-pouch Samsonite duffel that I used for souvenirs a couple of times. I actually was considering the Portland Gear backpack--I love the way it looks. My carryon usually holds my tech stuff, 3-1-1 items, journal (which is a handbound book), headphones, & miscellaneous stuff I use on the plane.

I'm having a little trouble visualizing your folding museum tote. Can you link to something like it?

My Tom Bihn zip top shop bag folds into its own pocket and I often carry it along for purchases during the day, groceries, etc. The padded handles are quite comfortable.

Luckily I don't have hiking days.

jeanm, believe me, as I was writing my post, I felt dizzied and thought, They're all gonna think I'm nuts.

Actually OP, I think it's nice to hear what works and also frankly what seems like a lot of luggage! I'm sure you learned a lot!! I don't buy much on trips, so I usually make it home with the same bags, but I too took a duffel bag that folded down when I needed to carry extra supplies for 3 months in Guatemala. (Came home packed in my checkin bag.)

Glad you are getting good advice!
The museum tote is from the Louvre gift shop and years old, but now there's even grocery bags with the same concept, like Baggu. Mine is plain black which is pretty much my color scheme!
Here's a museum gift shop option after a quick check:
https://shop.getty.edu/products/tote-bag-monet-sunrise-marine?pr_prod_strat=e5_desc&pr_rec_id=f79cddd0f&pr_rec_pid=6838505734336&pr_ref_pid=7259912700096&pr_seq=uniform
I would say mine is about 4x4 inches.
They hold a ton and I like that they're washable. I absolutely rely on it for my day bag, along with the tiny crossbody wallet (and sometimes a money belt).
Maybe this will work for your next trip!

I mentioned this in your other post but the reason your Briggs and Riley spinner is not going on the travel pro is just because that unique system Briggs and Riley uses really doesn’t work on anything but Briggs and Riley luggage. I have used my cabin spinner on both my ZDX, which is a bag I check and my baseline carry-on spinner and it works fine, but it does not work on another piece of luggage I have which has handle that looks similar.

Sandra, this cracked me up! I remember your love of bags (which I share) and I could totally see myself stocking up on items as I travel! Thanks for a fun and informative packing report!!!