I haven't traveled with the bag yet, but I bought this bag because I want to transport 1 pair of skis, one pair of boots, and some ski clothes, and it will do that perfectly fine. I laid my 2 skis (1 pair) separate from each other flat on the "floor" of the bag. My boots fit in the boot pockets just fine with the skis laying flat like that. If you have the skis hooked together by the bindings then they kind of interfere with the boot pockets. In other words, if you were trying to fit 2 pairs of skis and a pair of boots, you would have to be a little more creative, but you could probably fit it. It's just hard becuase the boots pockets go down into the bag where the ski tips and tails are, so if the skis aren't flat on the floor of the bag, the skis are in the way of where the boots need to go. I'm thinking the best way to fit 2 pairs of skis with a pair of boots would be to separate the skis, lay one pair flat on the bottom of the bag, and put the other pair up along the edges of the bag. That shouldn't interfere too much with the boot space. You might even be able to fit another pair of boots in the middle of the bag with the skis, but I'm not sure. Plus, that would probably make the bag overweight for a flight. You could probably do something similar with a snowboard and pair of skis if you laid the board flat in the middle of the bag and put the skis along the edges. Like I said, I haven't actually traveled with it yet, but so far the bag is just what I wanted.