Yes, you can technically both supercharge and turbocharge your car. However, it is very difficult to do well. The other large thing to mention is that you will not get much benefit from doing both -- only boost at low RPMs. The way Honda engines are designed to rev high, having boost at low RPMs is generally thought of as pointless.
As for your second question -- which would be faster. Keep in mind one thing, that the ITR engine is designed to be a NA beast. Therefore its really hard to tune it, and you end up having to change lots of stuff in order to get it working easily. A supercharger, from what I've heard around here, would slightly easier to tune on this engine. But to answer your question which would be faster... it all depends on how well you can drive in my opinion. If you have the engine FI, you are going to have ample power in any case. How well you can control that power dictates how fast you will go.
If you are going to do this think about one other thing -- how are you going to be putting this massive power to the ground without lots of tire spin?
Good luck.
