Looking for suggestions for a second bag for 14 days in Southern Italy

Well, everyone has their own likes and dislikes about bags. I usually bring a 21" spinner for carry-on (although I often check it) and a smaller personal bag, which is usually a backpack. I've brought totes before, but I find them a bit cumbersome to carry. Plus the smaller totes don't hold enough (for me) and the larger ones can get heavy on my shoulder. If you don't check a bag, it's probably not that big of a deal, since you can use the trolley sleeve on your suitcase, but since I usually do check a bag, I like to have my hands and arms unencumbered; hence the backpack.

With regards to which one, I've used a number of them. I have the Cotopaxi 20L backpack, which I thought I would like, but found it a bit too unorganized for me. I've also tried the Rick Steves Euro bag, which is probably the best bag at fitting a lot of items in a smaller space, but there are 2 qualifiers: it's not a backpack, and its shape tends to make it difficult to carry sometimes, as it protrudes a lot from the body.

My favorite bags so far have been the Roka Canfield Medium Backpack, which I like, but prefer something a bit larger; and the Calpak Glenroe Backpack (discontinued), which is almost perfect, except for its lack of a water bottle sleeve. But it holds a lot, is relatively lightweight, has pockets in good places, and a laptop sleeve.

I just bought a new bag that I will be trying out in a month when I head to London. It's made by Bagsmart, and so far it looks really nice. https://bagsmart.com/products/blast-quick-access-carry-on-travel-backpack?variant=41234573131858 It opens like a clamshell but has a separate pocket for shoes, a water bottle holder, and multiple pockets, including a laptop compartment. I especially like that I can access it like a clamshell. That was another slight issue with the Calpak backpack, as I had to dig down to the bottom if I needed anything. I will probably post a review of it after my upcoming trip, but I've read a number of reviews and so far, they are good.

FWIW, the bag is typically $70 for the standard (you can buy a version with an extension), but I got $14 off through a Capital One Shopping extension I use that runs codes through shopping sites to find discounts. I believe that Kohls also carries it.

I just realized you were looking for more of a day bag, not a personal bag for the plane. What I usually do is bring a small bag with me for being out during the day, but I flatten it and carry it in my suitcase or personal bag until I get to my destination.

I like small backpacks, and tend to use my Roka Canfield Small Backpack as a day bag when I'm out. That's probably what I will be using on my upcoming London/Paris trip. But I've also used a Sherpani Vale crossbody bag, or the Tom Bihn Medium Cafe bag. It really depends on where I'm going.

I do sometimes tend to shop while I'm out so I have some of the grocery totes that fold up with an elastic band and keep those in my day bag in case I buy something that won't fit. They're usually easier to carry than the bags the store might give you.

What you might do is take all your potential day bags, pack them with what you plan to bring with you, then go out for a few hours and walk around with each one, and see which is the most comfortable for you.

Like Mardee says, everyone has the day bag they like-my favorite is the Rick Steves Civita bag. That’s what I use on the plane as my personal item and then, on tour, I use it as my “bus” bag. It is very lightweight but also very strong. So during the day, walking around, etc, I bring a small crossbody bag that holds my phone, guidebook pages (I rip out appropriate chapters at home so I don’t lug the entire book), chapstick, scarf, eyedrops, etc, all the small things girls always have, plus a tiny rolled up grocery bag in case I buy something. In the Civita, which I leave on the bus,I have stuff that I might want to use during the day but don’t want to lug around - like my sweater, umbrella, snacks, sunscreen. And if I buy something at a stop (like a bottle of wine or some fruit, whatever), I put it in the Civita so back at the hotel I can easily schlep it to the room. And, good job using your money belt-great peace of mind!

You did not mention what month (guessing spring or fall based on raincoat?), but in cool seasons, I take a backpack that can fit a scarf, sweater, or jacket. In warm season, I don't like a backpack causing sweat, so I'd go with a cross-body that will hold a water bottle.
My fave water bottle (Swell) has a silicone hook that slips over the end, so I can attach it to a bag. Nice feature if you don't want to put it inside a bag.
Totes don't serve much purpose for me except when buying groceries.

I don't want to open the money belt debate (I'm a no), but I have always thought the point of the money belt is to prevent your important documents, credit cards and large cash from being stolen by a pickpocket (or, I suppose, carelessly misplaced?). In circumstances in which one would need a money belt for this purpose, a backpack would seem to be an invitation to thieves. E.g., I once had a woman unzip the top of my backpack on the escalator into the subway. I only knew this because she got in between me and my son, and he saw her do it.
I use a backpack as my personal item on the plane/train. My "everyday carry" (the fact that I know this expression pains me in a lot of ways) for travel is a packable cross-body bag. I have one that is large enough for a rain jacket or sweater in addition to the water bottle, etc. I need to take the Mardee's suggestion of trying this one out before my upcoming trip. Cross-body bags have been harder to use since my mastectomy. Turns out boobs serve the purpose of keeping the strap in place. Who knew?

Cross-body bags have been harder to use since my mastectomy. Turns out boobs serve the purpose of keeping the strap in place. Who knew?

G3rrycee, that is so true! I had a breast reduction a couple of years ago, and ever since then it's been difficult with crossbody bags. At least I don't have the boob-shelf that collected all the food spills anymore. :-) And I'm a no on the money belt, too.

I use the Tom Bihn Co-Pilot crossbody with the upgraded shoulder strap. As this strap has a rubberized underside that basically sticks to your shoulders, it maybe a solution for your situation.