Laptop/Messenger Bags

I'm going on an extended trip to Europe soon and I'm looking for something to carry my laptop, iPad, and gaming device (not sure what yet - Switch maybe?) as my "personal item" on flights. Does anyone have any personal favorites that won't break the bank? Bonus points for styyyyyyyyle.

I've had the Bag of Holding from Thinkgeek for about 6 or 7 years. It's pretty amazing how much garbage you can cram in this sucker. and at 50 bucks it's pretty affordable. http://www.thinkgeek.com/product/aaa5/

@bratcher_lev: I used that messenger back before going back to a backpack. My only issue with it is that the zippers are absolute trash. They broke so easily.

@bratcher_lev: That looks pretty great! I'll add it to my short list. Thanks!

I have this Manhatten portage bag

http://www.manhattanportage.com/catalog/deluxe-computer-p-404.html

It has a middle slot that is super padded for a laptop, and two slots adjacent that i keep a kindle in or books or whatever other weird device/object i'm carrying. Theres a front facing zipper slot which is great for cords and three front facing pockets that hold misc. items which are then secured when fhe cover is clipped down. Finally, it has an open back pocket for easy access items. Theres a range of sizes if the 13 inch is too small. (although i've fit a 15 inch laptop in the sleeve easily.) The build is very sturdy. The strap isn't padded on this size, so if you need to carry alot of weight for a long time it may be uncomfortable. Its maybe a bit pricey? But it is something you could keep forever. Mine was a gift so I was kind of surprised at how high the price was, I might owe the gifter a much belated extra thank you note.

Also if you're travelling, keep in mind the value of a bag that has pockets that can be secured from would be pick pockets. I saw another tourist get pickpocketed while i was in italy and it happened so fast i didn't even know what had been done until the guy was across the street and scot free!! I always kept my passport close on my person and most of my money too. Whatever messenger bag you get make sure the cover is tight over your items so that someone can't slip a hand in and grab something from underneath the lid. I don't know how this one would hold up against infiltration... you certainly couldn't get anything bigger than a cellphone out without undoing the strap?

If you're just taking this bag from the airport, onto a taxi and to the hotel, rather than walking around a city with it, that might not matter, but keep it in mind!

I've been looking for one for my laptop (to streamline for this next year so I can bring my laptop and a book and not need an entire backpack) but everything is super expensive because it's 17". Nearly everything seems to be made for 13, with some for 15 but after that it's disappointing. How big is your laptop?

I was looking at a couple but apparently I've lost all my recent bookmarks, go figure.

@beachgaara: I downsized to the XPS 13 last year so my laptop is a very portable one. That helps to fit all the weight and size requirements for personal item bags for sure.

@mikemcn: That's a great point about the pickpockets! I have heard several stores similar to that but never considered it when looking at different bags. I was considering a smaller backpack but I don't know if I would feel comfortable carrying something on my back that isn't secured.

In the same vein I'm not sure the best way to carry around my items that need to stay very safe like my wallet and passport when I'm out and about. I feel like they are things I should have at all times but I also don't want to risk compromising them.

Crumpler messenger and/or shoulder bags are pretty fantastic, if only for the good waterproofing and their fantastic durability. I've been using mine for going on 10 years now and it's held up without any wear and tear damage. On top of that I'd say they're designed pretty well, with good and sensible pockets and stuff. They are, unfortunately, not the cheapest things so that can be a bit of a barrier. But if you do get one they'll most definitely last long enough to be worth the money.

My recommendation is something like this for that stuff specifically:

I love Tom Bihn bags.
I have a small and large cafe bag along with a synapse 19 (backpack) and I'm ordering a Co-Pilot (travel bag) for an upcoming flight.
The stitching is great, the fabric holds up amazingly well and they're made in the USA (suck it Patagonia & Osprey).

I use the small cafe bag for normal outings with my toddler (holds epipen, diapers, wipes, iPad mini)
I use the large cafe bag for work (holds notebooks, Surface Pro 2, and a few odds and ends)
I like the Synapse for biking and packing for overnight trips

@artisanbreads: I've seen these as well as "money belts" and "travel organizers". All seem to serve the same purpose but I'm not sure which I would personally prefer. I have a small front-pocket wallet that I will use but I'm not sure if that is enough.

@bratcher_lev: if second this the bag is great and lots of storage for its size

I think my question is, "Will this just be the carry on" for flights and trains, or do you need something for carrying one or more of those items while walking, biking or driving around Europe for daily use?

If its just for the flights or trains I'd just picks up something at a "discount store" because it doesn't have to be rugged enough for daily use just transport safely. For daily use you want something were the stitching is solid and the zippers are snag proof, etc. Also, if you are walking around, biking, etc you actually want something that has backpack straps and isn't just a sling messenger bag. You can run or a bus, jump on a subway, or ride a bike with a messenger bag; but doing that every day is harder without a backpack design that you can really run with.

I have a Timbuk2 messenger bag, it very rugged, but on trips I find the bag often weighs more than what I am carrying around. I'm sure the whatever the hell the bag is made of (ballistic nylon?) would stop a 9mm bullet or fend off a dagger attack...but the bag is heavy.

What about a backpack? You can store the laptop and charger in the back pockets, an iPad in a smaller pocket, and a Switch, 3DS, or Vita somewhere in the middle. It may get a little snug with all three in there depending on the bag, but it's a good way to organize everything and it's easier to travel than carrying a separate bag or a briefcase.

Don't know the climate of where you're going exactly, but for passports and wallets, you might consider a coat with a button-able interior breast pocket. It's easy to access when you need it, stuff isn't likely to fall out, and things can't be easily grabbed without you noticing. A neck lanyard can work too, but there's the danger it marks you as a tourist and thus a potential target.