Never a DC-3, but I did get a ride in a Piper Cub once.
I got a ride in a J-3 when I was 13. Dad was a Flight Service Speciallist in the FAA stationed at the Barstow-Daggett Airport. A former Army airfield, the officers’ quarters were still there in a nice little neighbourhood. He lived in one of them. One day a young couple were grounded in their J-3 Cub due to the high winds that frequently blow in the Mojave Desert. Dad let them camp out at the house. (It was his habit to take in stranded pilots until they could continue their journeys.) The guy took me for a ride in his Cub, taking off from the ramp.
Another classic “workhorse” I have flown in is the De Havilland Rapide . It was only a nine seater but it did sterling service on many short routes.
That is really cool! I’d love to fly in one of those.
This UK company Air Alantique Classic Flights offers flights in them, they also have a couple of DC3’s on their books .
I flew in a DC3 from Rotorua to Christchurch when I was 2 or 3. I don’t remember it 
, but I am reliably informed (by my family at many opportunities) that I spent a good portion of the flight saying “det down, wanna det down” :smack:
More recently, I have have had lunch in a DC3
The CookieTime cafe, Mangaweka, NZ
Si
My first flight ever was in a J-3. I was a new member in the CAP, they had a deal where you volunteered to polish airplanes for a ride. We did a “breakfast” flight, from a small field near Akron, to Erie, Pa. On the trip up I flew front seat in the J-3 and on the return I think I was in an Aircoupe. I was 15-16 at the time and I recall thinking that the Cub was like flying in a box kite and the Aircoupe was more of a real airplane. In “earning” my flight I was also I was also introduced to “Neverdull”. 
Millions of years ago, my people and I came to this planet in a fleet of DC-3s equipped with rocket engines.
Flew in a DC-3 when I was very young, on a family holiday to Florence. For some reason it was decided that the Alitalia jet we were on didn’t have enough fuel to make it the whole way (I think it was a Caravelle, horrible things) so we stopped at Pisa and “hedge-hopped” in the Dac to a grass strip in Florence. I remember how low we flew, the square windows and that we pulled up next to what looked like a wooden garden shed
My Dad decided for a 75th birthday treat he wanted a flight in a Dragon Rapide So we booked a flight on one at Duxford and as ever my Dad was right – it was a truly lovely flight.
(Though you sort of know, even if you’ve never seen one, that a plane called a “De Havilland Dragon Rapide” will be beautiful and have lots of wings).
I think the reason you flew into Pisa is that even now Florence “airport” is too small to take large planes. The “grass strip” you talked about is that city’s main airport.
I can’t remember a lot of the details of the trip over after all this time, but it sticks in my mind that the stop at Pisa and the DC-3 hop were not part of the original plan - DC-3s would certainly have not been routinely used by that time (I’m not that old!)
But looking at a map I can’t see another way to Florence, as you say, the airport doesn’t take large planes; so now I’m puzzled! maybe we were just meant to pick up a Fokker F27?
And if that really was Florence airport, boy it was small! we certainly taxied on grass, I really couldn’t say after this time what we landed on, but when we got out the wheels were on grass
Never a DC-3, but my first-ever flight (in the late '60s) was on a Convair, probably a 540. Now that I think about it, it is still the only piston-engined airliner I’ve ever ridden in. I would do, er, unsavory things for a ride in a Constellation, or a Dragon Rapide for that matter.
While working in Guatemala in the mid '80s, I had numerous rides, and a couple of minor adventures, in a Pilatus Turbo Porter and De Havilland Twin Otter. The Porter in particular was bags of fun.
There was a national pilot strike sometime in the late 80s and the government supplied military aircraft as the substitute. DC-3s
You could fly on one for a song; no stewardesses, pre-flight emergency message, not much internal lighting and the canvas seats faced backwards.
I liked it a lot and flew often.
March, 1957, Braniff International Airlines, from Denver to San Antonio Texas for basic training in the Air Force.
It was my first trip and, possibly, in this very airplane.
Bob
I flew in one in Mexico, on a tourist jaunt from Cancun to Chichen Itza, around '93 or so.
Many times in the 70’s. Provincetown Boston Airways still flies them as far as I know. Very noisy from the props but I felt very safe.
Did he ask you whether you like gladiator movies? 
In the early 70s, I flew in a DC3, landing in Roanoke, VA. If you know your geography, you know how harrowing that was.
Bad enough in one of Piedmont’s 737’s.
PBA is yet another airline lost to history, along with plenty of other commuter lines in the region. Cape Air flies that territory now, with Colgan Airways covering northern New England.
PBA did have the highest-time DC-3 in the world, something over 90,000 hours the last I heard. I saw an ad for it in Trade-A-Plane recently, for a mill or so - somehow it found its way to Oregon.
I flew in a DC3 once on a scenic flight around Dunedin, NZ. I was up front, but I can’t remember if I was standing or if there is a “jump” seat in the DC3.
I used to work for a company that owned a deHavilland Domine (Dragon Rapide) but for some reason I never flew in it.
As far as J-3s go, I was once lucky enough to be hanging around when one landed at the local airfield. I got talking to the guy and he offered to let me fly it, solo, so I did. I encountered other feats of generosity at the same airfield. One chap had packed up his British registered Tiger Moth and was flying it around NZ. He sent me away in it for a quick blat.