Two weeks later, von Aschenbach is ready to leave Munich, and asks that his house in the German countryside be prepared for his arrival four weeks hence. He takes a train to Trieste, Italy, where he boards a ship for Pola. He stops at a resort on an island in the Adriatic, populated mainly by Austrian tourists. Von Aschenbach is dissatisfied with the location, decides he is in the wrong place, and boards a ship to Venice.
The ship employee who sells von Aschenbach his ticket attempts to impress him with tidbits about how wonderful Venice is, which annoys von Aschenbach. He enters the ship somewhat disgusted, and as he watches the second-class passengers board, he notices a group of young men joined by an older man wearing rouge and dressed gaudily to appear younger. Von Aschenbach finds this man's obvious attempts at recapturing his lost youth revolting. Later, he lunches in the hold of the ship, and again observes the same group of men. When the coastline comes into view, the young men on the ship celebrate, but their older companion has become pitifully drunk.
As the ship enters Venice, von Aschenbach recognizes several landmarks. He puts his luggage into a gondola, and the rouged man drunkenly wishes him a pleasant stay. Von Aschenbach reflects on how like a coffin a gondola is, and realizes that the gondolier is not taking him to his requested destination, the pier. The gondolier explains that the pier will not accept luggage, and refuses the writer's request to turn back. A gondola holding musicians passes, and von Aschenbach gives them money. When von Aschenbach's gondola arrives at a landing stage, he disembarks, and the gondolier disappears before von Aschenbach can pay him. A nearby old beggar explains that he is the only unlicensed gondolier in Venice, and didn't want to be caught by the municipal officials on the pier.
Von Aschenbach is expected at his hotel and is greeted with respect. He takes a cup of tea on the terrace and then goes for a walk. Later in the day, he arrives for dinner too early and takes the chance to observe the other guests in the lobby. He notices that all nationalities are represented, but a Polish family consisting of three girls, ages fifteen to seventeen, and a beautiful boy of about fourteen accompanied by a governess, particularly interests him. Once in the dining room, he notices the boy's classically Greek symmetrical beauty. The girls are dressed severely and appear nun-like, while the boy has long curling hair and is clearly the favorite of the family. The children are dining with their mother, and when they leave after their meal, the boy glances back at Von Aschenbach.
The next morning, the weather is still quite gray. Von Aschenbach finds himself depressed and considers leaving Venice. At breakfast, he notes that the beautiful boy is allowed to sleep well into the morning while his sisters are awake very early. Later in the morning, he sees the boy wading in the ocean and admires his beautiful legs. On the beach, the boy leads a group of about ten children. By listening to the children playing, von Aschenbach discovers that the boy is named is Tadzio, and that his closest friend is Jasiu.
At noon, von Aschenbach returns to his room and studies his old face and gray hair in the mirror. During lunch, he gets a closer look at Tadzio and notices his teeth do not look well, meaning he is most likely sickly. That afternoon, von Aschenbach goes to Venice to take a walk, and feels feverish as a result of the crowd and sirocco. He realizes the pollution of the city makes him sick, and decides to travel to a different location. The next morning, von Aschenbach tries to leave. At breakfast, when he sees Tadzio, he almost changes his mind, but decides to continue his course. However, Von Aschenbach's luggage is put on the wrong train, forcing him to stay in Venice at least temporarily. Von Aschenbach finds himself surprisingly happy upon learning of this setback, and returns to the hotel. However, upon admitting that the reason for his happiness is Tadzio's presence, he despairs.
Here, Mann begins to rely increasingly on the literary technique of leitmotif. Various details are subtly repeated to create meaning. Von Aschenbach's discomfort on the boat to Venice is made clear by the reoccurrence of sordid details concerning the trip. The boat is grubby, the water is filthy, and his fellow passengers smell strange and are badly behaved. Mann splices these details in with other aspects of von Aschenbach's consciousness, making the section appear less like an intentional indictment of the voyage.
The most ominous section of this chapter is when von Aschenbach 's is unable to control his gondolier. Von Aschenbach immediately notes that the gondola feels like a coffin, an allusion to death, and then cannot control where his gondolier takes him. This encounter subtly echoes his encounter with the stranger in the Munich graveyard, another clear symbol of death. The gondolier and the graveyard stranger are strikingly similar, as they both have red hair and prominent teeth: the graveyard stranger bares his teeth in a strange grimace, and the gondolier shows his teeth with the effort of rowing. In addition, both men have specific hats. The stranger's is made of bast, and the gondolier's is a, "shapeless straw hat beginning to unravel." The unraveling hat perhaps symbolizes the onset of chaos in von Aschenbach's otherwise highly ascetic existence. Clearly, the graveyard stranger and the gondolier are highly similar, a repetition that illustrates destiny, not coincidence, has brought von Aschenbach to Venice.