I had so many good times that it's hard to pick a favorite. Had an absolute blast when I joined my first faction, the XA. Later on, just about every time I undocked as my Buccaneer were good times.
There was that time that my Buccaneer got married. We held a Zoner trader at gunpoint and forced him to preform the ceremony, with the BPA's Lucy Silsbury sitting there the whole time unable to do anything about it.
Another good time was when we escaped a BAF fleet in Leeds, only to run into the Joker in Manchester, making for the same hole we just left. We warned him that he wouldn't like what he found.
Robbing a Shetland under the guns of the Fleet Admiral's Destroyer. Threatened to blow up the transport if he made any hostile moves. We got paid and got away cleanly.
Looking way back to my XA days, right after I got promoted to Royal, we went on a rampage through Colorado. By the time we were done, we had killed every hostile in the system. Practically destroyed the system itself before the dust had settled.
I remember one Bowex convoy I was in. We had a clydesdale with us (all in Shires), and a pirate let the big ships pass and tried to pirate the Clydesdale. He didn't like it at all when four Shires turned back for him....