Aschenbach embarks on his journey approximately two weeks after the events in Chapter 1. He first travels to an Adriatic island but finds that its rainy climate and provincial flavor do not satisfy his longing for a "fantastic mutation of normal reality"; ten days after his arrival, he leaves for Venice.
Boarding the boat that will take him to this city rising from the sea, Aschenbach is met by a shabby hunchbacked seaman. A man with a goatee and the mannerisms of a circus director takes his money and hands him his ticket. Both men are showily obsequious and distastefully ingratiating, as if fearing that their customer will change his mind about the voyage. Aschenbach watches a group of noisily laughing and joking young men also on board the ship. Upon closer examination of one of the more conspicuous of the group, Aschenbach realizes to his horror that this particular "young man" is in fact quite old and wrinkled: His rosy cheeks are painted on, his hair is a wig, his moustache dyed, his teeth false. He wonders whether the other merrymakers simply do not notice. Suddenly, Aschenbach feels that the world around him is becoming strange and dreamlike; as the steamer begins to withdraw from shore, he feels an "irrational alarm." However, the uniform grayness of sea and sky soon lull Aschenbach into a state of sleep.
Although in previous trips to the city he has always been greeted by sun, Aschenbach finds the sky over Venice to be heavy with clouds, making it appear to him a "different Venice" than before. Again he sights the gaudy old man, now disgustingly drunk and gesturing lewdly. Once more Aschenbach feels the world spinning out of control. As he disembarks, the man approaches him, drooling and repellant, smiling phonily and extending his compliments to Aschenbach's "sweetheart."
Aschenbach steps into the gondola that will take him on the next part of his journey: The black boat is likened to a coffin and linked with death, "the last journey." Seating himself, however, Aschenbach feels not a sense of dread, but rather one of lulling luxury; he yields to a drowsy languor. However, he notices with a start that the gondola is headed out to sea rather than to the vaporetto stop where he had intended to take the smaller boat that would bring him to his hotel. He quarrels with the argumentative gondolier, who has reddish eyebrows and often bares his white teeth as he struggles to guide the boat. The man refuses to turn the boat around or to inform his passenger of how much the ride will cost, saying simply, "You will pay." Aschenbach again feels himself sinking into a torpor. They reach the shore and Aschenbach goes to get change to pay the gondolier, but upon returning, he finds the man has vanished. An old man tells him that the gondolier owns no license, is a known criminal, and left to avoid the police.
The story's location in Venice is highly significant: Italy represents the sensuous south, in contrast to Aschenbach's austere native Germany; Aschenbach's physical journey from one culture to the other and from one climate to the other parallels his internal descent from cool control to fiery passion. In particular, the city of Venice can be seen as a symbol for Aschenbach himself: Venice is unique for its daring construction; it is a city built in the middle of a lagoon, built and maintained by sheer will over the forces of nature. Similarly, Aschenbach considers true art to be the victory of the will over physical needs and natural impulses (see summary of Chapter 2), and he considers himself to have accomplished such victories. Yet it is also well known that despite its mask of glory, Venice is gradually sinking, literally rotting from within; again, the same might be said of Aschenbach.
As in previous chapters, ominous portents abound. The employees on the steamer make such a show that we begin to question their intents; they seem to issue from a world of artifice and fraud. The unexpectedly gray sky creates a dismal atmosphere. The grotesque old man not only suggests deceit but also embodies Aschenbach's fears about himself: Might Aschenbach's pursuit of relaxation move him toward a similar degradation into lust and baseness, a similar loss of all dignity in old age? The gondola is a clear symbol of death, and the criminal gondolier evokes the ominous figure from Chapter 1 whose appearance first gave Aschenbach the idea to travel. His statement "You will pay" is exceedingly ominous. The journey in the gondola also suggests the voyage to the Underworld taken by many classical heroes, such as Odysseus, Theseus, and Hercules: These heroes entered the realm of the dead by crossing the River Styx at the hands of the skeletal boatman Charon. The episode is only one of a multitude of references to Greek myth, and, as with many of these references, it functions as parody: while the classical heroes' crossings were proof of their strength and determination, Aschenbach's crossing is marked by a weak surrender. Moreover, this is only the first in what will become a pattern for Aschenbach of apathy and surrender to mindlessness and physical comfort.