Tora-san gets into an argument with his uncle and sets out on the road again. In Kyushu he meets a young woman named Keiko and the shy zoologist Saburō, and attempts to play matchmaker between the two when they all return to Tokyo.
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.
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.
Traveling salesman Kuruma Torajirō falls in love with an inn manager as New Year's approaches.
Tora-san visits brother-in-law Hiroshi's hometown to attend a memorial service for his late father. When the local temple priest becomes intoxicated, Tora-san wearing the priest's robe delivers the memorial speech, much to his family's surprise. Thinking he's found his true calling, Tora-san decides to join the order, and falls for the priest's divorced daughter.
Tora-san's opinions about Americans get challenged when another wandering peddler Michael Jordan stops by Shibamata.
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, 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 and ruining Sakura's chance to marry someone, as well as just being a real pain to those around him. There is a sentimental side to him also, and the best way to describe him is that he grows on you.
After winning big at the races, Torajiro Kuruma wants to take his aunt and uncle on a trip to Hawaii to partly pay the great filial debt he feels he owes them, but the plan hits a snag. Also, a pretty kindergarten teacher rents a room at Toraya.
Taking a message from Hiroshi's father to heart, Torajiro attempts to give up his wandering ways.
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.
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.
After Torajiro's latest attempt to find a bride goes awry, he starts traveling again and runs into Utako (last seen in Tora-san's Dear Old Home), now a widow.
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.
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 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.
Tora-san's nephew Mitsuo is exchanging letters with Izumi, a former classmate whose parents divorced and took her out of Tokyo.
In Nagasaki, Tora-san and an acquaintance help an old woman who has fallen and injured herself. She invites them to her home where the three share a night of eating and drinking. The old woman's health deteriorates and she dies. At her funeral, Tora-san falls in love with the old woman's daughter, but winds up acting as a go-between for her and a young law student.
After a friend and business colleague dies, Tora-san visits the man's daughter, then takes her to Tokyo so she can study for a night school exam.
In Shibamata, Tokyo, Tora-san's family prepares for a wedding. Meanwhile, the traveling Tora-san meets an old acqaintance in Iwate Province. Tora-san refuses to drink with him, afraid that the acquaintance, now settled and married, will again become attracted to Tora-san's wandering existence. Tora-san becomes attracted to a female barber, but must break off their relationship so that she too can live a secure life. She instead gets into an abusive relationship with a motorcyclist.