what tire brand? For example, if you look on tirerack for MSC2 295/30/20, they will tell you the min and max wheel width. I believe for 295/30/20 they recommend 10.5" - 11.5" wheel (check to confirm this). 11" being the best fit. 9.5" was stock on 981 Boxster and that is too small. Even if you could find a shop to try to fit the tire, it would not perform properly, and probably would not be safe. I have not checked on the stock 718 Boxster wheel sizes, which I assume you are asking about.
Should you go to a wider tire? Depends on your driving style, goals, etc. Depends on your suspension, wheels, brakes, etc. Lots to consider. It's a slippery slope, so don't just do it because you found a good deal on a few tires.