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First-generation Caymans were quite at home on twisty highways or road courses. Base models were quick enough for most drivers, while the Cayman S’s performance rivaled the base 911 coupe that cost significantly more. The Cayman held two people and had about double the luggage space of the Boxster. If you weren’t the manual-shifting type, you could opt for a five speed ‘Tiptronic’ automatic on pre-2010 versions, or the really excellent automated manual (PDK) transmission on later models.