Travel bag suited for Italy

DH forsook his trusty nylon day bag for a Tom Bihn messenger bag a few years ago and has been quite happy with it. They come in various sizes- DH uses the larger laptop bag.

I don't have any suggestions for bags for boys, but I love my Baggallini crossbody bag. I think mine is the "Hobo", but there are many versions to choose from. It comes in lots of colors, is very light weight but sturdy nylon, holds just enough stuff for a day out and best of all, has a pocket on each side for a water bottle/sunglasses/umbrella, etc. It sits close to the body so it looks and feels small, but holds a lot if you need it to. I took it to Italy in 2017 and it was perfect. We were supposed to go again this summer, but now am waiting to reschedule the trip! Baggallini is sold in a lot of stores. Amazon has some. I have gotten one at Marshalls and there are a lot on ebay, too.

Unfortunately, Baggallini has added the unnecessary RFID protection to a lot of its bags, so they probably aren't as light as they used to be.

I would suggest that any of the bags you've mentioned might not be allowed in a museum and that you could be required to check them or put them in a locker.

For example the Borghese in Rome required that anything bigger than the smallest of purses be checked. When I was there in 2017, my typically tiny purse like this one was okay. Anything much bigger had to be checked. My phone easily fits in a crossbody purse like that.

You might take a look at Sea to Summit products. They'd also probably require checking at the Borghese, but they're ultra light and strong and will stay that way if you don't pack them too full.

On my trip to Portugal and Spain last summer, I used this crossbody messenger style Sling bag.

I also used this day pack, but it seems to be unavailable. This slightly different day pack or this slightly smaller day pack might actually be better for your needs.

The Tom Bihn messenger comes in several sizes, but as mentioned, some museums still mean checking your bag. I still prefer something that zips at the top, but at least the Bihn is designed to be difficult to get sneaky fingers into.

If it were me, I'd just use the bag you have if it worked on previous trip. Checking the bag at museums - just leave it at the hotel on those days, and use a plastic shopping bag for your water and maps. I'd never carry a phone in any bag, so anything in my bag is expendable. No bag is safe from a sharp knife, but the risk of pickpockets and thieves is much lower than the impression you may have. Your awareness of surroundings, and never putting a bag down or on a chair unattended is pretty standard advice in most big cities anywhere.

Note: I use the Civita as my day bag. From the pictures it looks like it has a shape but it doesn't. There's no stiff form or fabric that holds it in shape. Empty, its collapses to a scrunchable size with the strength of a empty pillowcase. It works fine for me, and if you dont pack it full, doesn't get much scrutiny at museums. Just pointing that out as you can get misleading impressions form the website photos.

I agree about the Civita - have been using it for years and have it with me right now on a stateside trip. I‘ve tried (and own) three or four other day packs (generally looking for slightly smaller and/or lighter weight), but all of them annoy me for one reason or another. My ancient Civita is my pal.

I have used the Civita day bag for many years. I currently have an older model and a newer model and both are still serviceable. Two years ago I used the newer one and loaned the older one to a friend to use in Paris and only had to check it when it was stuffed pretty full or when I carried it with a umbrella into a museum. I did not Check it at Versailles. The older bag has survived trips to China, Japan, serval trips to Europe and lots of day trips here at home and still looks almost new. The bag is really pretty formless and I found that I’ve been able to use it most everywhere and stuff a lot in it when needed. Last year, I used In Rome and Malta and did not have to check it at the Vatican. You can wad it up and stuff it under your arm like a purse and it looks pretty small, but It also holds a lot. That said, you never know when you might have to check it in some museum. I found that I did have to check it at some museums in St. Petersburg but it was stuffed with rain jacket, umbrella and lenses for a SLR (which I don’t carry any more). Ifound that the best thing with this bag is just make it as small as you can and tuck it under your arm like a purse and DON’T ASK, DON’T TELL. if you have to check it. Usually nobody says anything and it goes right through. If it is stuffed fully and worn as a complete backpack you might get flagged. The beauty is you don’t have to wear it with both straps as a backpack and only one strap around one shoulder as Rick does with his. I usually don’t use this as my carry on for an airplane. I use a slightly larger backpack that holds a little bit more and is more formed and fits on my suitcase. When empty, this weighs almost nothing and is easily packed in the suitcase ready for day trips.