Depends on your driving preferences. If you're a power guy, then the 997S is the choice. No question. But if you prefer handling and can forgo a bit of power, then the Cayman is an unbelievable car. I'm a mid-engine fan and a handling guy and just love driving the Cay/Box cars. They just rotate so nicely and quickly.
My issue is that I really wanted a Cab and really can't get over the design of the Boxster. It is just fundamentally unattractive to my eye.
But if I was looking at a hardtop, a modified Cayman would be king of the road for me. Someday, I'm sure I will.

 

Maybe I'm just too small (5'10", 150) to notice this, but I've always thought they were fairly similar in size. The Motortrend comparison article seems to agree with me too:

2006 Porsche 911 Carrera | 2006 Porsche Cayman S
Headroom, f/r 38.0/ 26.0 in | 37.8 / - in
Legroom, f/r 44.0 / 26.0 in (est) | 44.0 / - in (est)
Shoulder room, f/r 51.5 / 47.3 in | 51.5 / - in

I don't have a 997 handy to test, but I can't imagine 0.2 inches of headroom really being so noticeable.

 

I had the same issue. I am 6'1" and 195 lbs and just felted cramped in my '06 CaymanS. Having said that, it was the single best handling car I have ever driven. It just needs a little more grunt ....with 350+hp/300+ tq this car would be absolutely phenominal. I don't get caught up in the "it's not the iconic 911" BS. Drive what you like not what others like.

 

I think you ask a great question...one that many have faced. Back in '06 I ordered the Cayman S. I liked the traditional mid-engine platform and the driving dynamics that come along with it. I don't track my car but you don't have to in order to enjoy it. I'm not into stoplight racing so the 295 hp is enough - it would be better with a little more hp though.

What are you looking to do with the car (DD, weekend toy, etc)? I've gotten to the point where I want to enjoy the car with my wife and daughter and that means I'm going to move to a 997S cab. I'm glad I had the chance to enjoy the Cayman but my needs have changed. Once you ask yourself how you're going to use it and what's important to you, you'll have your answer.

Good luck!

 

I had an 06 Cayman S for three years and traded in on an 09 C2S Cab. The Cayman is nimble and much easier to intuitively drive fast. The 997, despite enormous refinement, still must be consciously driven fast w/ the "slow in, fast out" mentality. There is more leg room in the 997 than the 987 (my wife has an 08 Boxster LE). The seats Porsche uses are all the same so the shoulder issues will be the same. The 997 gets the nod in terms of presence because it is the "icon", but both the Boxster and Cayman are elemental sports cars and pure Porsche in both form and substance. I'd drive both and determine what suits your needs best. If you're a real sports car enthusiast the nonsense promulgated by the uninformed about the Cayman and Boxster (stigma/chick/etc) should be easy to ignore.

 

Having been through roughly the same situation: I went in to buy a Cayman 2.7, then test drove the Cayman S to see what I was missing. Given that the price for a used Cayman S was pretty close to a similarly used 911 C2, I drove the C2 (not the S - that was out of my price range).

My take away:

Cayman 2.7 was a nice daily driver, but not much of thrill.
Cayman S - the car I drove had PASM, Sport Chrono - and it was a beast. It handled well, but ultimately felt a little rough around the edges - the way a track car should.
911 C2 - Sublime perfection and I ultimately ended up getting this car.

There were things the 911 just did better (more comfortable, different sound, etc) that sold me on the 911 as opposed to the Cayman S.

HTH

 

It's funny how different impressions are when driving. I actually like the steering "feel" a tad better in the Cayman, probably due to the weight distribution. I've always felt that the steering felt a little light in the 911.

that said, I dont think there's much of a comparison overall, hence my owning a 997. My biggest niggle against the Cayman—the business end looks so, well, not visually appealing.

 

i drove an 08 cayman s for 500 miles.


once you get over the f'd up step child looks of the damn thing, its actually a very nice driver. its just plain ugly as compared to the 911, everyone knows it including porsche and cayman owners.

an aero kit and body upgrades are like lipstick on a pig for this car. might as well drive it raw if you're going to own it.

lastly, i cant even imagine you would ask this question given the looks of the cayman...

 

Maybe because not eveyone's #1 priority when purchasing a car is the way it looks?

 

I think the Cayman is a great looking car. I prefer the 911, but the Cayman is very unique and cool.

 

I like the way Cayman looks, but it looks like a young kids car... If you were a 20 year old, and was going to college I would say go for it

 

Isn't it great Porsche give you the choice?

 

3yrs ago I was shopping a 2002-2005 996 C4S vs a new 06 CS. I liked the 996 C4S better. The CS is a great handling car but I thought it was too short on power compared with the 996 C4S

If you're looking to auto x or do track days, the CS is probably the better car because of the mid engine layout.

If was was shopping a 997 S with a CS, I would defintiely go with the 997S

 

The way they measure size is deceiving. They put the lower part of the seat in the most rearward position and adjust the backrest to suit. Since the backrest angle that would be most comfortable is more reclined than the bulkhead of the cayman will allow, you have to move the lower seat forward a few inches to allow a proper backrest angle. Furthermore, if you have a headroom issue, you can recline the seat of a 997 till you fall over backward. When I drove the cayman, my legs were simply too long to be comfortable. I could however, move the seat back further than it was, but you sit bolt-upright. (great for the track, bad for the street) Sadly, that was a deal-breaker for me on the cayman. Since I like to autocross the car, the 911 was a major compromise in handling. But, the extra power, room, and character of the 997 is a great consolation for the understeer.......

 

I had an 08 Cayman S for a loaner for a good while as my engine was being replaced...the Cayman S was great, but was shy on torque...the 09's with DFI should be better. The Cayman S is a very well balanced car with great lines and has a very nice sound to it.