I still have my log book so I know exactly, it was Nov 3, 1969 at Albert Whitted Airport in downtown St. Petersburg, today that's right behind the Dali Museum. It was a Piper Cherokee, the call sign was 8269 November. I was 19 years old and started flying lessons that day, they were $16 an hour for the plane and $5 for the instructor, $21 total. Today I believe it's about $125 an hour for plane and instructor. The Cherokee looks like this, it's a low wing plane versus a Cessa 150 which is a trainer with a high wing.
First time on an airliner was Saturday April 4, 1970 from Jacksonville to Ft. Polk, Louisiana for Army Basic Training. I had taken the Greyhound Bus from St. Petersburg to Jacksonville on Wednesday and checked into the rather drab Ambassador Hotel in downtown Jacksonville. There was about 200 of us staying the night on the Army's dollar and the next day we were all sworn in at the induction center. Several buses pulled up to the building and they said for everyone to board a bus, you're going to Ft. Jackson, South Carolina for basic except for, and then they called my name. They said that since you have an aviation MOS, you must go to Ft. Polk for basic and the only way to get there is to fly. However, due to the controller's sickout, you need to go back to the Ambassador and stay until Saturday, that's the earliest we can get you a flight. So it was somewhat ironic that my first two days in the Army were spent in a hotel in downtown Jacksonville because I had enlisted to become an air traffic controller, but I wasn't able to leave because of the controller's sickout.
Eventually I took a Delta Airlines jet to Atlanta, changed planes and then boarded another Delta jet to New Orleans. Then I took a step back in time and boarded a Trans Texas Airline DC 3. Later at Ft. Polk I would learn that TTA Airline stood for "Tree Top Airline" because when we were at the firing range and a TTA DC 3 was inbound we had to stop firing until it passed. It looked like this and they actually flew down range just above the tree tops.