My first flight when I was 8 was in a DC-7, Eastern Airlines from Baltimore Friendship (what is now BWI) to Miami. (I returned home on a jet, the Convair 880, on Northeast Airlines.) A few years later, we took a family trip to Florida, and my Dad saved money by booking us on a prop flight (4 hours) vs. a Jet flight (2 hours). Turbulence the whole way, it was like riding a roller coaster. I don't remember the airline, but it might have been United, if they flew from Philadelphia to Miami. I'm not sure what kind of prop planes United was flying in the early 1960s, and I don't remember what we flew.
Another notable trip was a Scout trip to the National Jamboree in 1969, where our local scouting council had a breakdown in making travel arrangements, and a bunch of us were stuck flying home from Spokane, Washington on a DC-4 from a local charter airline, Johnson Flying Services. That was a slow flight, 13 hours to get from Spokane to Philly, with a refueling stop in Rockford, Il. We had some pretty bad turbulence crossing the Rockies, but the rest of the flight, even over the Appalachians, was pretty smooth. We apparently dropped off the radar at one point, which caused some anxiety to parents waiting for us to arrive in Philly. When we got to Philly, the pilot, who had never been east of the Mississippi, was confused about where to take us, and wanted to drop us off at the FBO for general aviation instead of the terminal, where everybody was waiting for us.
My first wife's father was a private pilot, and he flew my then-wife and me up to Maine a couple of times. His first plane (a single engine 4-seater, which I don't remember the model) had limited range, so for our Teterboro - Maine flight, we had to stop in Concord, NH to refuel. Then he decided to fly right over the White Mountains, which were starting to cloud up. That was a bit of a thrill, seeing the ground rise up under you, and then fall off, plus flying in and out of clouds. But we were flying at 7,000 feet, so there was no chance we were going to hit any mountains. Later, he bought a Beechcraft Debonair, which was a bit bigger and faster and had more range, and figured out he could avoid the weather by flying right up the Connecticut River Vally. You'd putter along at 8 -9,000 feet in perfectly clear, smooth weather and see the clouds covering the White Mountains to the east and the Green Mountains to the west. That was in the early 1980s, and was the last time I ever flew in a piston-powered plane, though I took a few prop-jet commuter flights since.