Carrying a bag full of samples, Mitsuo makes rounds to shoe stores in remote cities. While staying at budget hotels, his thoughts turn to Tora-san.
When Tora-san's infatuation with his nephew's school teacher causes family turmoil, he leaves on his travels again. When he returns, he falls in love with the teacher's mother.
Tora-san befriends the descendant of a feudal lord. The man asks Tora to locate his deceased son's wife who resides somewhere in Tokyo.
After Hiroshi is injured in a workplace accident, Torajiro gives Sakura the money he has saved and leaves to work as a traveling salesman once again. During his travels, Torajiro meets a father who shares a drink with him. In the morning, Torajiro is shocked to learn that the man has left his baby behind and a note asking Tora to take care of the child.
Tora-san is inspired to pursue an education after a visit to the grave of a woman he met years ago. When he returns to Shibamata with the intent to study, he falls for Toraya's new tenant instead.
Tora-san visits Hokkaido and is reunited with Lily. Now divorced, she plans to resume her singing career and renews her unusual relationship with Tora-san.
Tora befriends a pretty barbershop owner and runs into Izumi. When Tora twists his ankle, Mitsuo comes to care for him and see Izumi. Meanwhile, Izumi must choose between her new job in Tokyo and returning to Nagoya to care for her mother.
Tora-san's nephew Mitsuo is exchanging letters with Izumi, a former classmate whose parents divorced and took her out of Tokyo.
Tora-san becomes friends with Toraya's newest tenant, a pachinko-playing electrician that goes by the nickname Watt. Tora attempts to match Watt with a young waitress.
After a chance encounter with Hiroshi's father on a bus, Tora decides to get serious and reflect on the mortality of man. His plans are derailed when a beautiful lady starts working at Toraya.
When Izumi can't stand seeing her mother flirt with other men, she leaves home. She sends a letter to Mitsuo and Mitsuo goes looking for her. But Izumi unexpectedly meets Tora-san.
Tora-san, an itinerant peddler who is thrown out of his father's house twenty years before but reconnects with his aunt, uncle and sister Sakura. Tora wreaks some havoc in their lives, like getting drunk and silly at a marriage meeting.
When cabaret singer Lily writes Toraya about her illness, Tora-san rushes to Okinawa to be by her side.
Tora-san leaves Shibamata once again after an argument with his family and finds himself at an inn where he meets Tomekichi, a young man who looks up to Tora-san.
Tora-san's family's neighbor, Akemi, who had been married in Marriage Counselor Tora-san (1984), runs away from her husband, who is only interested in work. Tora-san follows her to Shikinejima, and attempts to bring her back to her home. In doing so he encounters a school-reunion group who are traveling to meet their elementary school teacher, which is a reference to the film Twenty-Four Eyes by Keisuke Kinoshita. Tora-san joins them and falls in love with the teacher.
During his travels, Tora-san comes across a traditional theater he used to visit, and discovers that one of his old friends has died. Tora-san and his family help the friend's daughter, who becomes romantically involved with an aspiring artist.
A playboy-gambler friend of Tora-san’s dies and, abandoned by his mother, his little boy suddenly turns up in Shibamata. Searching for the boy’s mother, Tora-san meets a cosmetics saleslady and the three become a surrogate family, with Tora-san as “daddy”.
In his travels through Japan, Tora-san meets and falls in love with a female doctor, however he is afraid of committing to a relationship.
During his wandering throughout Japan, Tora-san meets a suicidal man. He travels with the man to Vienna, but winds up homesick for Japan.
Mitsuo goes to Nagoya to visit Izumi, whose father left Izumi’s sad, bar hostess mother for another woman, so together they decide to confront him in Oita. Meanwhile, Izumi’s mother befriends Tora-san and together they travel to Oita to meet them, with Tora-san quickly falling for her en route.