A routine I’ve enjoyed is spending time every year in Hong Kong while my wife works on performances in her home city. This trip I am swamped with assignments but technology has made it much easier to work on the road. Here is my list of gear to bring for illustration based on years of traveling:

15 inch Macbook Pro with Retina display- Otto Steininger gave me advice that 15 inch was the optimum size for working on the road and it’s been great advice. I use a 27inch iMac at home but don’t even miss it with the Retina display 15 inch.
Intuos 4×5 tablet-
iPad Pro with Apple Pencil- Pair this with both AstroPad with turns the iPad into a cintiq like device. Procreate is a wonderful standalone app for creating images. The iPad Pro is my dream drawing tablet for travel.
Dropbox Pro account- Having all projects and files on the cloud has made assignments infinitely easier when traveling back and forth. It has also made keeping track of business records much less painful.
Lacie 1TB portable drive- Even with the cloud, it’s a good idea to have a copy of all the files you may need. Also used to back up the laptop.
Multiple input international power adaptor. The Monster Outlets to Go 200 travel adaptor is my favorite and I can plug all my gear into it.
extension cord for the Macbook Pro.
External mobile battery pack. I use a Mophie Powerstation but sure there are many great brands.
Small sketchbook and pens.
Bose Headphones. Who doesn’t need their music?

I could see a day when I don’t bring the Intuos pad but the line quality is a little different than working with the iPad so it’s nice to have it handy. With the iPad I don’t need to have sketchpads anymore but still like to keep a sketchbook handy. All this fits easily into a backpack with plenty of room to spare.