How to effectively organize documents when traveling?

After I get visa, ticket, insurance, hotel bookings etc, I scan everything, as individual pdfs.

Two types of documents, one which are crucial for journey, others which are just for help. Then I make two folders on my dropbox, Important and Informative. Visa, flight ticket, hotel booking, insurance, tickets, passport info page etc pdfs go to Important. Travel guides, tours, map, weather info etc go to Informative. Then I merge all pdfs in each folder as a new pdf, print two copies of each on A5 double side. Staple each copy on top left corner.

A5 size makes them smaller enough to store, while keeping them easily readable. Double side printing also cuts the volume in half.

One set of Important goes in luggage, second stays with me in my camera-cum-document bag, along with original passport.

Both booklet copies of Informative pdf stays in luggage. I use one on vacation, second is as backup, just in case.

Originals are only my passport, my national ID, money cards etc.

Edit: I also carry a ziplock or two, almost of A5 size, and I shove all the receipts, bills, tokens etc I get while on vacation in them, and sort it when I am back home.

Edit2: I use FolderSync Android App to keep this folder two-way synced with my phone, and almost all the times airlines hotels etc are ok with a soft copy of the document, as they just need a number to locate my data in their systems.

I keep on me: Passport, insurances card, wallet (id, money...)

I keep on iPhone: Plane e-tickets. Hotel/accommodations reservations and confirmation emails.

I keep in a craft envelop in my hand luggage duplicate printout of every confirmation I received by emails.

Emails are also stored in the cloud (hotmail/gmail...) to be easily accessed in internet café if needed.

Passport and credit cards scans (photos) are sent by emails to myself and GF (and vice-versa) so that they are stored in the cloud if necessary.

As Richard wrote, I dump all unnecessary documents in my luggage for sorting and recycling when traveling back home.

I will share a recent experience of mine.

We were going to go on a holiday on X-Mas and I scanned and saved all the important documents in my laptop which was with me all the time.

It was connected to Dropbox and so did my Phone and I thought oh well I will have all the copies in my smart phone for quick access where I can't take out my laptop.

We were about to reach First Country and had to fill their immigration cards given by the airline, took out phone to see our Passport details and found out that I forgot to Sync the phone with Dropbox (Anti-virus had blocked it from running in the background). I could do nothing but laugh at my foolishness.

Moral: Don't just assume documents will be there. Double check them.

But one thing that i did good was that i printed all those and put them in a file in my laptop bag and Numbered them in a sequence i was expecting to use them.

1. Tickets
2. Copies of Passports, Visa and Insurance
3. Airport Transfer Booking
4. Hotel Booking
5. Tour Booking
6. Transfer Out Booking

Then next numbers for the second country. I found that simple 1,2,3 sequencing so helpful all the way throughout both the countries that we visited. There were at least 15 bookings and that sequence made it so much easy.

This file was in the documents section of my laptop bag which was a back pack, every time we reached the next stop where we needed the documents My wife would just take out next numbered document from my bag which was on my back and there you go, no fuss. Didn't even need to take-off the bag in a line (no i'm not lazy, just that I had our baby, who doesn't like a stroller, in my arms :P ).

Every time one print out was used, I put a cross on it and moved it to the back of the file.

Not entirely sure if people will like it as an answer to this question though :D

For paper documents, I use a bunch of plastic folders. I group the documents in the folders depending on when I have to use them. It is possible to use different colors on the folders in order to distinguish between them. Anyway, they are semitransparent, so you will see on the text on one document which folder you have.

For me the only way to organise these sort of things is each printout in the order you're going to use them, then throw things away as you use them.

E.g. if you are going to drive to the airport, then get on a plane, then pick up a hire car when you land, to then drive to the hotel to check in I'd order the print outs like this:

1. airport parking details
2. airport checkin details
3. car hire details
4. hotel details
5. return flight checkin details

Remember to throw stuff away - e.g. after I check-in for the plane, I will have thrown away sheets 1 & 2, meaning sheet 3 (car hire details) is on the top for when I go to pick up the hire car. This makes it super quick and easy - just pull out the first/top sheet and you're done.

Protip: if one print out is on multiple sheets, make sure to staple them together to make it easier to handle.

For short/simple trips I just put these print outs in a simple A4 envelope and leave it in my carry-on bag.

Protip: write the important stuff on the outside of the envelope in big writing - flight numbers & times, terminals, hotel address etc. This means you can easily get that info quick if you're in a rush.

For longer/complex trips with lots of reservations I put the print-outs into a "display book" which is a bunch of A4 plastic envelopers bound into a book so I can just flip through them all. The display books are cheap and light - I've used them on long trips with 30 or 40 reservations for various things and they work really well to keep everything neat too.

Of course these paper print-outs are backups. I will have most of it available/pinned-for-offline on my phone.

I have a small (A5) Moleskine notebook that I use for travelling. In the inside cover I write things that rarely change and will be the same throughout multiple trips, such as my passport number (in case it gets lost), card numbers, phone numbers for my bank (in case I need to cancel my cards), etc. Then on the individual pages I write the details of each aspect of the trip in chronological order. These pages are easy to remove after the trip/before the next one.

For flights, I'll have the airport, airline, flight number, terminal (if applicable) and departure time. For hotels (or, more likely now, airbnbs), the name, address, telephone number, booking confirmation number, dates of my stay.

It's small enough to fit in a pocket, is just a bit bigger (though a fair amount thicker) than my passport, and has an elasticated strap for keeping the cover closed, so I can slip my passport inside that to keep them together.

On my phone, I generally have the airbnb app, the app for United, and I star/flag confirmation e-mails so I can find them quickly if required. I also tend to carry a second battery when travelling so I don't have to worry so much about the battery potentially dying.

In terms of printing, as little as possible. Generally only things I (might) need to pass through border control in the country I'm travelling to (e.g. a print out of my flight reservation(s) to prove I have a return ticket) and anything where they explicitly state they don't accept electronic copies/e-tickets (I travelled by Greyhound between Seattle and Spokane as part of a trip to the US last year, they only accepted a printed version of the ticket).

Receipts that I accumulate during the trip just go in my wallet to be sorted out when I get home.