I have not owned both but I have driven the 2010 Boxster, Cayman and Carrera S.
If I could only have one car then the choice would be the Carrera S. It has more cabin room, a more upright seating position and better visibilty. For long trips it would be a more comfortable interior. It is taller and thus other drivers seem to see it more than with the Boxster/Cayman.
For winter driving the 4S would be my choice.
For me I don't have only one car, I have six (not bragging, just don't like to sell stuff, I am a hoarder) so the Boxster/Cayman was my choice.
I like sitting lower to the ground, I like the fact that it feels like more of a sports car than the Carrera S.
I have done five hour trips in my Boxster and found it to be quite comfortable. Best thing to do is go to the dealership and drive them all. Then decide.
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2001 Boxster S 3.6L, Zeintop
"Calling upon my years of experience, I froze at the controls." - Stirling Moss
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