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.

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 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.

寅次郎收到莉莉從沖繩寄來的信，原來她在夜總會唱歌時暈倒入院，還說：「臨死前，很想見寅一面」。寅馬上趕到沖繩照顧莉莉，縱然闊別了五年，兩人的感情有增無減，莉莉休養期間，寅更隨傳隨到，旁人都以為他們是夫妻……淺丘瑠璃子演的莉莉第三度登場，叫寅再三考慮「結婚問題」。山田自言「這是我最愛的作品之一」，渥美清去世後，山田在《男人之苦》系列中只選了本片(加插新片段)推出特別版來紀念這位一代巨星。 Upon receipt of a letter from Lily telling Tora that she would like to see him before she dies, Tora rushes to Okinawa, where Lily has fainted during one of her performances. Although five years has passed since they parted, the former couple continues to care about each other, and Tora nurses Lily to health. The personal favourite of Yamada Yoji , Tora-san's Tropical Fever was the only film re-released (with added scenes) by the director to commemorate Atsumi Kiyoshi after the superstar's death.

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.

On the road again, Torajiro meets a kindred spirit in Lily, a lounge singer.

When Tora-san returns to visit his family, he is surprised to find an arrogant professor occupying his room. The professor and Tora-san become rivals for the affection of Chiyo.

While Sakura and Hiroshi struggle to save funds to build a house, Torajiro befriends three young women on vacation during his travels.

After an encounter with a dying yakuza's son and at his sister Sakura's urging, Torajiro attempts to change his vagrant lifestyle and become an honest worker with a steady job.

寅次郎赚了些钱，决定要请照顾妹妹多年的叔叔、婶婶，参加旅行社的豪华团去趟夏威夷。两老要出国的消息很快传遍了整个柴又!但命运总爱捉弄寅次郎，替他安排行程的经济人携款潜逃，叫他们好梦成空 。为了免遭人奚落，他们决定晚上才摸黑回柴又，然后躲它个三、五天再现身......

1969 film. 1st entry in "Otoko wa Tsurai yo" series.