In the last year, I've spent a lot of time on the road, mainly through client work and the European projects I've been involved with. To be more exact, I've spent more than half of my time traveling. This year should definitely be more light on conferences!
Now, people have very different styles of traveling. Some plan everything in advance, and pack for every possible contingency. But not me.
Over the years I've built a style of traveling that involves very minimal planning and late arrangements. This can fire back — making flights or trains more costly, but it is still often worth it through the added flexibility. Maybe there is a meeting or a conference that pops up at the last moment, and can be combined with the trip with minimal detours?
An important component of that is to have travel gear that gives you the needed flexibility. For me this means a largish backpack that can carry all the work gear I need, and also fit about a week's worth of clothes and other things I need on daily basis. No need to wonder what extra to pack when the space is limited, and no need to check in luggage when flying.
And even more importantly, having a light and easy to carry bag so that you can just keep it with you for a day out in the city instead of having to first visit the hotel to drop it.
My current backpack is a Haglöfs Connect 17" that I got last Christmas. Prior to that, I was traveling with another backpack that I originally acquired for the long walk to Santiago de Compostela. That backpack was great for anything from daily commute to month-long trips around Europe, but was starting to be quite beaten up.
The new one is slightly smaller, more stylish, and most importantly, organized better. Now, for instance, I have a separate compartment just for my computer and its accessories. This makes airport security a lot smoother than trying to dig the computer up from behind clothes and other random things before putting it on the tray.
To keep the bag organized, I have an Eagle Creek packing cube to keep my clothes together, and occasionally one of their shirt folders whenever more businessy attire is required. I also have two toiletry bags, one of the actual toiletries and the other for cables and whatever adapters I need to connect when giving presentations.
One week's worth of clothes can sound like too little, given that often the trips can be longer than that. The solution for this is to use either laundromats, or, in a pinch, to pay for hotel laundy service.
All you need for travel is a good backpack. The Pack Lite blog shows other examples of packing lite for both work and holiday travel.