I went from factory 17's to Gemballa Competition 18's that are wider than stock by 1" in front and 2 1/2" in back. I went with the Porsche recommended tire sizes with the switch to 18's and while I did notice a minute increase in cornering ability, I did not notice any loss of ride comfort. Now, I did do this after only owning the Boxster for a month and a half, so I may have noticed a much bigger difference if I had upgraded after driving on the 17's for 6 months to a year.
I worry about potholes, curbs, etc. with the 18's....primarily due to the shorter sidewall and lack of sidewall bulge to protect the wheels. I lucked into the set of Gemballa's for less than the price of one, so if I were to trash one wheel, it would cost as much to replace the one wheel as I paid for the full set.
I can't imagine what it would be like with 19's as the tires would be nothing more than a rubber band wrapped around the rim. It would look pretty cool, but I don't think I would drive it as aggressively due to a fear of damage to the rim(s). My Boxster begs to be driven aggressively, so I would be defeating the purpose of buying the car in the first place.
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