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In terms of performance, the Cayman S is better than the 335.
However, you have to think of other factors, that is, if they are factors for your situation.
I was torn between these very two cars last year as well.
These were my thoughts:
Cayman S is a sports car and carries more status symbol. It's not as common (at least here).
Cayman S performs better
Cayman S is a porsche... and I'd love to own one (a porsche) one day.
Reasons why I went for 335
I live in northeast with brutal winters. X-Drive helps here.
I travel a lot and need the luggage space. 4 doors helps here.
Comfort. I drive long trips (commute is 2 hrs of twisty roads each way). Sit in a Cayman S for a few hours... not nearly as comfy (seats, cabin electronics, etc).
If I went w/ Cayman S, i'd have to get a secondary car. I found 335 to be a happy medium.
If these factors aren't factors for you, then go for the cayman s and let me live vicariously through you.
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