I test drove an Boxster S with tiptronic today, 987. I was actually very surprised - it's a pretty good transmission and very sporty; in auto it held the gear when I was really on it, and it seemed to shift pretty well with the buttons. You have to time it correctly, but in general it was not as slow as I was fearing - actually pretty usable as a fun shifting transmission.
It was a 2005 S - would a base 2007 Cayman have the same transmission? Sporty and hold gears, etc?
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