Personally l would go with the 996 with special options

deff. the 996. not even a comparison

l ask myself this question regularly, especially since even the mighty 996 turbo has fallen (for '01 & '02 models) into the same price range as a well-optioned Cayman S. They r quite different cars, so only u can answer based on what you're after.

First off, forget the Cayman without the ''S'' if you're comparing to a 996 Carrera -- u give up too much HP in a base Cayman to compare it to a Carrera. So comparing a 996 to a Cayman S, u first have to consider the mid- vs rear engine experience, & then the ''brand new with the latest tech'' vs ''used with somewhat older tech question.'' Hand in hand with that is the depreciation factor. You can pay $69K for a brand new Cayman S that is going to depreciate a lot immediately, or the same price for an '03 to '05 Carrera (there r lots of cars in the $69K range, & the years available at that price vary by body style, drive train, options & engine config) that is still going to depreciate but has already taken its single biggest hit. Thanks to that depreciation, the Carreras look like a bargain compared to the Cayman S, but that is offset by the advantages of being the original owner.

The 996 will have more straight line power, more ''bite off the line,'' but once the two r running in the twisties, it will come down to the driver. Some people prefer the lighter mid-engine layout, & some prefer the rear engine experience with its predictible (once u practice) oversteer characteristics -- u need to drive them both (aggressively) & see which fits u best. Of course, the back ''seats'' in the 996 r not worth considering in the equation, unless u have young children or legless midgets in ur family. Trunk space actually goes to the Cayman, l believe. When it comes down to the engine, my Porsche mechanic would, without a second is hesitation, tell u they r both absolute crap to be avoided at all costs, & that only a turbo or GT3 is worth considering in any Porsche after the 993. l would personally like to disbelieve him, but he has pretty strong credentials, & there certainly have been a lot of problems with the 986/996/987/997 engine.

To summarize, there probably is no right or wrong choice -- just an educated choice tempered by personal preference. Have fun!

The 996.

l would take a stripped 996, without all the weight-sapping junk.

But, still, either would be a fine steed~!