Cayman.

Though I don't have a modern 911 to compare it to..

My 911 is 50 years old, and not street legal

My 914 is 44 years old...and not street legal..

I have a now long in the tooth Cayman... 2007... what a wonderful car.. it fits and works, handles if I shift my eyes and my hands move the wheel.. the car just goes there..

Rudtner keeps whispering in my ear to make it a track car.. I am resisting with this one..

I had a very stock '88 911 years ago that I daily drove for almost 5 years. A little over 5 years ago, I got back into Porsche ownership. At the time I test drove a few boxsters and caymans (base and S) and also a 996 TT. I assume the 996 TT should be like the 996 C4S but faster. I didn't take much of a test ride in it, but it was boring. I've often wondered if it had issues. It was at a stealership in town. I ended up gravitating towards Coxsters (really didn't care which, just whichever felt like "the one" when I found it. I ended up with a 2008 Boxster S.

To me, the 987.1 cars felt more like modern versions of my old 911 than anything else (but, honestly, still worlds apart). I had 2 miata between my old 911 and the Boxster S, and the Boxster S is also like a miata, but on a completely different level.

The 996 TT that I drove didn't feel that fast, certainly not much faster than my boxster (although I'm sure it was, it just didn't feel faster).

I'll bet the 996 TT that I drove would have been a great LONG road trip car. I've driven my boxster S several hours, and I enjoy it. I'd be happy to drive my Boxster S for 8 hours, but I suspect the 996 TT that I drove would be even more comfy for that sort of drive.

For most of the rest of my driving, the Boxster is a bit more alive and sporty feeling.

If this was going to be an "extra" car, and I had the same money to spend for a good quality drivers car, I'd love to have an '87-89 911. They in some ways are on a different level from the newer Porsches. The newer Porsches are faster, more capable, and better at most things. The older porsches have je ne sais quoi or "soul."

From a pure pleasure of driving and ownership point of view for me
1 '88 911 (217hp)
2 '08 Boxster S (303hp)
3 '01 911 turbo (415hp)

From a fun and capable and reliable and comfortable (A/C, stereo, don't smell the heat exchangers) point of view
1 '08 Boxster S
2 '88 911
3 '01 911 turbo

The key, is what sort of driving are you going to do?

The 996 can be easily retrofit with some sort of IMS solution.
The 987 is less likely to need any sort of IMS solution, but if it does, it's a PITA
The 987 will be newer and more modern which may or may not be a good thing, but most would consider it so (it's not like we're comparing an SC to a 981)

Meh...

They are both great Porsches. It's not like you're comparing a 928 to a 911 or a Panamera to a 911.

Based on driving feel, the 987 is in many ways more like a classic 911 than the 996 that I drove. I'm not saying the 996 was a bad car at all.

I think there might have been something wrong with the 996TT if it did not feel fast Steve. Did you get on it at all? They are by no means violently fast feeling like the early single turbo cars, but they are very fast capable cars. Albeit a little soft, but that is more due to the age of the suspension.

I will agree that they are great highway / road trip cars.

If it was me I would drive a few examples of each to get a good feeling overall.

Oh yeah, I got on it a few times. It just didn't feel as fast as I thought it should. It may have been either that it wasn't making full power, or it could have been that the power delivery was so smooth and steady, that it never gave you that punch in the butt that a peakier power curve gives.

I did only drive that one and one naturally aspirated 996, so my sample size was very low on those.

They are definitely more of a steadier building of power in stock form. I kept mine completely stock, but they do accept power upgrades very easily.

I loved my 986 S. That’s one I might try to get back. Not as fun as a Miata imo but a much better car if that makes sense.
I guess the answer is drive both and see what does it for ya. They are all great.

I owned a few 911s including a 993 TT. My DFI Cayman S is my daily driver (beside stupid trucks and SUVs). Telll you the truth, I wanted my 993 to be my favorite but it just fall short in the way of driver impute and feel. Don't get me wrong, the 993 is an awesome car, but the Cayman S just feel more awesome (also its 15 years newer tech). Its down on HP, but it feels just as fast up to about 90 or 100mph. After that, the 993 really shines, but who's going that fast daily? Maybe its the PDK, its quick, thinks for me and extremely easy to drive. Love me some new 4 banger turbo Cayman S or GT4. I haven't driven neither, but love one for daily when I grow up.

I drove my 930 the other day. Its felt planted and heavy. There's something about those older air cool 911s. The feel like they are carved from a granite on the hwy

Would you say the same if you had to pick between a 904 and a similar era 911?

Because that's really what the Cayman is, it's the 904 of it's day.
It just has the engine handicap because of marketing.. But it is the better drivers car of the 2.

Hell, even for GTLM Porsche now races a Cayman... they took away the power handicap... and called it a 911 RSR.. But really it is a Super Cayman RSR, and they just won IMSA with it.

It even has the access panel behind the driver to adjust the belts, like a Cayman has.

https://i.ytimg.com/vi/2BarDQ2Bckw/maxresdefault.jpg

Marginally.. It might be easier to drop the engine out of a 911.
But that's not something anybody does all to often.

At the same time you can take the tranny off a Cayman with engine still in the car.
That makes a clutch job easier (again, not something that anybody does regulary)

Most things can be done with the engine in the car. there are access panels and there is room.
Annoying things, Like coolant distribution pipe..
Can be done by just dropping the engine at the front for 5-6 inches..

It's all doable. Just need to approach things in the right order and from the right angle. bit of savoir faire..

Thanks for the input. I was thinking more regular stuff like checking the pullley on alternator. Pop hood and shake. My boxster I had to remove the carpet and then the panel. As you said though, not something one does to often. I honestly haven’t really worked on the 996 yet, knock on wood.

carpet comes out in 1 minute
7 nuts
panel comes off in 2 (or 1 minute if you use a pneumatic ratched)
It's a bit slower then opening the hood, I agree, but there's a good tensioner and pulleys don't really come loose on their own after 12 years

You are much faster than me. If that is my only complaint about the Cayman, I think that's not so bad.

Cayman is the new 911
911 is a bloated luxo barge.

That maybe true, but drive one in the canyon and tell me after you have had a chance to push it around the corners then report back. Its sure quiet and the power delivery is damn linear and powerful. I drove a friend's 2016 S. The damn thing is somehow connected to my brain through blue tooth. Its just doesn't whatever steering input ou ask of it. For a daily driver, that's not a bad car to have but I still like my Cayman S better. It feels like a much smaller car when thrown into the corners

Well it was untill they neutered it with the fart 4 engine.
Current Cayman is the new 912

I’ve owned multiple of both, it’s Cayman all the way for me. Especially compared to a 996 cab which is easily the least loved modern 911 (just look at the prices). Comparing the two the Cayman will have a nicer interior, better more tossable handling, more practical storage, better MPG, likely better feature content, and IMHO much better styling. The 996 will have the edge in straight line performance but that’s about it.

It may not sound the part, but it's faster and more powerful with a fatter power curve than the 6 cyl Cayman/Boxsters that it replaced.

Maybe the comparison would be better if it was comparing a guy 6' and relatively fit to someone like Jet Li, Jackie Chan or Bruce Lee. They may be smaller, but they're probably going to take him in a fight.

It's absolutely true, but people haven't flocked to them either. The sound has been panned universally, and I guess folks don't love the idea of a 4 banger in an expensive Porsche. All the special 718 models are back on flat 6s (GT4, spyder), and apparently the next model will be...electric. So I guess Porsche gave up on the idea as well?! MPG was no better than the 6 in real life, but turbos did give way more torque ! They could be the next great used porsche bargain IMO if you don't mind the subaru noise (there might be good exhaust alternatives by then).

To me the 981 was the high point of Cayman production - looks and engine wise, especially the spyder/GT4 - I'd love one of those someday... I don't buy a Porsche because I *need* one, I buy it because it put a smile on my face, and a zinging 6cyl at 7200 rpm pleases me way more than a rush or torque from a farting 4 at 2500 rpm.

PS: I too am pleasantly surprised the Cayman walked this opinion poll. I've said that all along (and I owned a 996 and Cayman S in succession). I'd add that the 991 shifted the playing field, the wheelbase/track of that car gave it a more Cayman-like turn-in while retaining its superior 911 traction. IMO the 991 whoops the Cayman of the same era, but on the original topic, clear victory for the Cayman of that era over the 996.

External look of the 987 is better if you ask me..
the 981 718 angular bits up front just don't appeal to me..
the rear quarters , meh..

The inside is nicer , so I would reckon the 987.2 with dfi is the best of both worlds..

The 718 fart 4 engine, the thing i hate is just mostly the sound of the turbo burble .
I've heard several various aftermarket exhausts, they all just sound louder of the same.. I can't like it. though they are obviously faster.

I'de rather have a high revving NA flat 4 that get's closer to 904 carrera engine sounds... (though the intake sound will be hard to replicate)