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Having both, I frequently get asked which one I like better. I reply it's like picking your favorite child (altho I don't have any that I know of). Each has its purpose and unique characteristics for being cut from the same cloth.
But here are a couple of questions that may help you decide...
Do you do DEs? That to me would be the only place the 50% more HP would be worth having. Your Boxster is plenty capable on the street. Racing from stop light to stop light will get old. And I've never gone around a corner and thought I needed 160 more HP.
Do you not take the Boxster places because you're concerned about someone cutting the top? I'm less concerned about the Cayman at places like a movie theater. I tend to only drive the Boxster to places where I trust the surroundings.
But if I had to pick one, there's nothing like driving to work on a summer morning with the top down. I do that a whole lot more than the 3-4 DEs per yr.
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GPRPCA Chief Driving Instructor
2008 Boxster S Limited Edition #005
2008 Cayman S Sport - Signal Green
1989 928 S4 5 spd - black
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