I agree with most all of the above posts. I didn't think I could afford a CS, so when the base Cayman came out I took a test drive in one. A great car, but the base Cayman just didn't seem worth it to me (and I had it on a variety of roads). Then I decided to try a CS as long as I was there.

The rest, as they say, is history. I had to get a CS. I found a used one in the color I wanted, with lots of good options on it for a great price, surprisingly quickly. 26,000 miles later, the CS is still the car for me - on track, in the twisties, autocrossing, daily driving, you name it.

So you may want to do a full test drive in a CS....

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Others have made a good point about the Interstate not being the place to test drive the car. If you own a Miata, you know sportscars are for the twisties. However, besides that, I'm guessing the connection issue is far simpler ...

The Cayman is too big for you.

I'm serious here. My wife finds the Cayman very big. Your Miata is probably two feet smaller than the Cayman. It's also probably much less wide and lighter (not sure of the width or weight differences). This might sound like a simple thing but size does matter.

If your used to a small car, particularly in length, the Cayman will be far less intimate and you will feel far less connected to it, especially coming from a Convertable. You'd probably do a lot better looking at a base 987.

We came from a MINI. The MINI "felt" fast. It "felt" connected and with lowered suspension, it felt much more stiff than the CS. However, the "feeling" of fast and being more connected to the car was a mere illusion of size. The CS, for example, was much faster and far better handling than a small MINI. The cayman just "works". You just turn, no drama.

I strongly suggest you read this article Porsche Cayman S Revisited | The Truth About Cars In particular, get down to the last paragraph about how the Cayman lacks a soul and there is nothing that tugs at the heartstrings. BUT, it's all about the driving and its the ultimate drivers car. That journalist got a lot of it right. The car is not dramatic. It just works.

Porsches are not about being the fastest, the quickest accelerating, or whatever. Rather, it's the overall holistic experience about the entire car being a driver's car. After you own one and live with one for awhile, you come to understand the difference between a total driver's car and other cars that make compromises.

YMMV

Miatas are great cars. That is why you see so many at the track. I agree that you should try the Boxster. If it doesn't float your boat, heck you tried the Porsche and it wasn't for you.

I have had a similar experience comparing a Chrysler 300SRT8 to a Mercedes sedan. I like the feel of the SRT8. Objectively better in my opinion. And a bargain to boot.

Go with your gut and enjoy the journey. Buying a car should be fun.

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2007 Speed Yellow Cayman GT 2.7 (retired)
2008 Guards Red Cayman GT 3.4
"Carpe Cayman"

My thoughts exactly. I "WANT" to like this car. I guess I certainly like the car, but for 65-70 thousand, I should be "LOVING" this car. I don't know what it is, I'm probably 80% sold on it, but something to me is missing. Maybe I need to spend more time with the car than just a 1/2 hour test drive.

I'm debating getting the Cayman or a M3. Two different breeds. GT vs. Sports Car.

Who knows???

Try the Cayman S, it will give you a bit of a wake up. The extra cost will be worth it

The Cayman may be too composed for your taste. What was the limit in your other car is short of the limit in the Cayman and therefore doesn't give you that same on-the-edge thrill. I know that taking my CS through the same corners and same speed as I have other in my other cars, doesn't produce the same feeling of speed. I contribute this to a number of factors including less body roll and exhaust noise, but mainly to the fact I am comfortably in control of the car. You would really have to push yourself hard to find the edge on the Cayman, and generally to the point that you shouldn't be doing it on public streets.

For me it came down to this question:

Do you want to feel the speed or do you want to control it?