Boxster S definitly over the Cayman. I drive a Boxster and over the weekend I got an opportunity to drive the Cayman. It is a really great car with slick lines although I am not that crazy about the rooflines especially over the cockpit, it is a bit too contoured and bubble like. From a handling perspective it is actually quite difficult to compare the two, comparing a coupe to a convertible is not really comparing apples with apples, each has their pros and cons. From a performance point of view the 07 987S has the same engine now as the Cayman S so that is not really a discussion anymore. Pricing is a no-brainer for obvious reasons. IMO, it comes down to whether you want a convertible or not. I live in Johannesburg South Africa where the sun always shines, like in Florida and there is nothing better than cruising on a sunny sunday afternoon (or Mon, Tues, Wed, Thurs, Fri and Sat ) with the top down....something to think about. Good luck with the decision and remember at the end of the day you will be driving a Porsche and that in itself is just a fantastic experience.