I go on much longer trips but here's what I pack. 22" Rollaboard: 2 Uniform Shirts 1 Uniform pants 7 Sets of undershirts/boxers/socks (3 white/4 black) 1 Pair of hiking pants (can wear them multiple days, wash them in the hotel sink if you need to) 2-3 other shirts (at least one with a collar) 1 Fleece 1 Packable lightweight down jacket 1 set of workout shorts/shirt 1 pair of running shoes 1 Toiletry kit 35L backpack 1 DSLR camera and three lenses 1 Gorillapod (small tripod for camera) 1 Laptop 1 Work iPad 1 Portable espresso maker/ground espresso 1 long sleeve exoficio shirt to wear in cruise 1 Bag of assorted chargers and adaptors. 1 A book/magazine It's definitely a learning curve. For your first 6 months to a year you'll be dragging around crap that you will never use. When you're unpacking at the end of a trip look through and make note of what you didn't use the entire time you were out.