There’s an old saying in the world of car values that when the top goes down, the price goes up. Indeed, if you look at just about any of our favorite classic cars, the convertible versions command a premium. Exceptions to the rule are few and far between, and are mostly limited to Mercedes-Benz 300SLs and 1963 Corvettes. Add one more: the Porsche Boxster/Cayman twins.
While technically separate models, they are too similar to think of separately since they have the same engines, same chassis, same basic shape, and essentially the same options. But despite the Boxster offering that wind-in-your-hair, top-down motoring experience that so often translates to value, a comparably equipped Cayman, with its fixed roof, tends to command a few grand more than a Boxster on the second-hand market.
The reasons for this anomaly are pretty straightforward. The first and most obvious explanation is that the Cayman has always been more expensive, even when it was new. Convertibles usually cost more when they come straight from the dealer, so the Cayman bucked the trend from the beginning. It is also more enthusiast-focused, given its track-use potential and stiffer structure. And it has never had to deal with the stigma of being the cheapest car in the Porsche lineup, a title the Boxster has carried, along with the 912, 914, and 924 that came before it.
The Boxster was first introduced for the 1997 model year, when it and the 911 were the only two models the company sold. While the mid-engine Boxster shared components and styling cues with the upcoming water-cooled 996-generation 911 and had design inspiration from classic favorites like the 550 Spyder, the Boxster was the “cheap Porsche” right from the get-go. Even though praise was nearly universal for the fun-to-drive little roadster, it was seen as a car for people who couldn’t afford a 911, and that view hasn’t really changed.
A second-generation Boxster was introduced at the Paris Motor Show in 2004, alongside the new 997 generation of the 911. Porsche identified a big price gap between the entry-level Boxster and the flagship 911, so to fill it they made a more driver-focused fixed roof version of the Boxster rather than come up with the design and tooling for a whole new model.
Upon its introduction for 2006, the Cayman weighed a bit less than the Boxster and, thanks to its fixed roof, had significantly more torsional rigidity, allowing for stiffer suspension and anti-roll bars that translated to all-around better handling. Upon introduction, the Cayman was also solely available as an S model with a 3.4-liter Boxster-based engine that was topped with cylinder heads and the VarioCam Plus valve timing system from the 911. A less powerful 2.7-liter base-model Cayman followed shortly thereafter, and in 2007 the Boxster was updated with the same engines. A facelift in 2009 also saw a bump in displacement and horsepower. The engine design also no longer used the intermediate shaft that had previously proven problematic, so post-2009 models are considered quite a bit more desirable.
The Cayman, which came about a decade after the Boxster, had a very different beginning. It was always priced higher than the Boxster, it always came with a little bit more power, and from the beginning it was even more of a smash hit in the automotive press than the Boxster had been. It won numerous magazine awards as pundits claimed that, in terms of driving dynamics and performance, it rivaled the sacred and much more expensive 911. In the 2006 “Best Driver’s Car” test for Britain’s Autocar, the Cayman S won outright and bumped the 911 Turbo down to third place—writer Chris Harris even proclaimed that the base Cayman “has better steering than any 997, a more attractive cabin, and still retains the same generic feel to the controls.” These kinds of comparisons were just never made with the Boxster, which was never seen as a rival to the larger rear-engine Porsche.
With that said, aside from the obvious difference (one doesn’t have a fixed roof, the other does), similarly-equipped, Boxsters and Caymans behave much the same in the vast majority of everyday driving situations. The Cayman, however, weighs less and ultimately performs better owing to its fixed roof. Plus it has more power, is more accomplished on the race track, is rarer (since it was produced for a shorter period), and left the dealer with a higher price tag than the Boxster to begin with. That’s enough for the car to defy the usual collector car logic.
In the case of the Boxster, when the top goes down, so does the price. And it will likely always be that way.