I recently took this on a week vacation to Cabo and although I had another bag, I could have packed everything in here. I packed 4 pairs of board shorts, 4 pairs of shorts, 2 pairs of pants, about 8 t-shirts, 3 polo shirts, 3 collared shirts as well as toiletries, a spare pair of flip flops and underwear. I also detached the small backpack and put my computer, AC cord, iPod, camera, passport, wallet and headphones in it. Be warned that it will not fit a 15 in computer though. I have a 15 in MacBook and it stuck out the top, not a huge deal for me though. I rolled that load most of the time but carried it in backpack mode though the airport when rolling wasnt convienient and it wasnt a problem, I'm a 6'1" 180 lb guy though. If you're a tall thin female with back issues I would roll the main bag and carry the small pack all of the time. That being said, I am extremely happy with this purchase, the bag(s) are incredibly well made and sharp looking. It fit perfectly into a Continental overhead compartment (with the smaller bag under my seat).