It is difficult to discuss "Family" without discussing the trauma Captain Picard experienced before it. Suffice it to say, he takes a well-deserved leave of absence from his captaining duties to return home to his family's French vineyard to reconnect with his estranged brother. The emotionally guarded Picard is deeply honest here, written pitch-perfectly by future-Battlestar Galactica showrunner Ronald D. Moore.
The setup for "Captain's Holiday" is exactly what it sounds like. Picard takes a vacation on a pleasure planet but finds himself nearly-immediately thrown amidst intrigue largely due to a beautiful woman named Vash. Together the two embark on an archeological adventure with time travelers abound.
A series finale is a tricky thing, but Star Trek: The Next Generation manages to satisfy a great deal of the fanbase with theirs. It does so by playing with time jumps. Picard is forced to reckon with his past, his present and his future, the last of which fans may expect to return to with the upcoming sequel series.
Star Trek: The Next Generation was often at its best when it got metaphysical. Also written by Ronald D. Moore, "Tapestry" sees Picard die and be given a sort of A Christmas Carol treatment. He is shown to see how his life would have been had he made a different decision at a critical turning point of his life.
In a stunning season-ending cliffhanger, Captain Picard finds himself a victim of the Borg, a hive mind of organisms with bionic implants. As a result of this assimilation, he is party to atrocities that haunt him throughout the rest of the show and in large part make Picard the compelling character he is.