The next morning, Dicey finds Sammy crouching by himself at the edge of the lawn. When she approaches him, he confesses that he had a dream that the other children had abandoned him, and then asks Dicey why she had planned to travel alone. Dicey tries to explain, pointing out that she is completely unsure of how their grandmother will receive them, and ends by reassuring Sammy that she was going to come back for them, no matter what. She confesses, to Sammy's dismay, that she had made a mistake in planning to travel without them. The Tillermans make their way down to the dock, and before long, Tom and Jerry arrive and begin rigging up the boat, explaining to Dicey that they must first tack, or zigzag back and forth across the wind, on their way out of the harbor.
Once they are on the water, Dicey is mesmerized by the boat's easy swiftness. She revels in her sense of being part of this easy motion and salty, sunny air. She finds herself wishing she could have a house on a boat, and compares people and families to different types of boats, looking for harbor. Dicey realizes she does not really want a harbor, but instead longs for constant change and exploration. When they reach the middle of the bay, the wind dies, and Dicey asks if she can steer. Jerry gladly hands the tiller to her, and Dicey becomes accustomed to the feel of the boat so that, when the wind picks up, she continues to steer competently. Jerry explains that he enjoys Tom pushing him to be rebellious, as it challenges him not to live a "life of quiet desperation." Dicey expresses her skepticism, and much to her surprise, Jerry tells her he wishes she were older, implying that he is interested in her as a girlfriend. Dicey flushes under the compliment. When they dock the boat, Tom and Jerry make plans to party with their friends, and Dicey and her siblings slip off, buying food and finding a resting place by an empty house on the water. Dicey uses her new Swiss Army knife to open a can of soup, and the children sleep on top of new ponchos.
They wake the next morning and begin their trek, through Easton and towards Salisbury on the back roads. Before long, they stumble upon a circus, and James insists on eating lunch there. While James is peering into a tent, however, an irate woman, Claire, accuses him of trespassing and threatens to call the police. Before she can, however, a friendly African American man named Will tells Claire to leave them alone. He politely escorts them off the property, explaining the circus does not open until evening. When Dicey asks him about the circus, he explains how much he loves traveling around. The children find themselves walking between fields of corn and tomatoes, and before they find their resting place for the night, Dicey notices a sign advertising work as pickers. They make camp by a creek, and Dicey finds herself wondering aloud at the appeal of always moving around from place to place. Maybeth quietly insists that they must have a home. Sammy remembers that Momma used to cry when thinking of her mother, their grandmother. The children dismiss the thought and begin to sing.
Tom and Jerry's first maneuver as they sail across the bay mirrors the Tillerman's progress toward their grandmother's house and toward their ultimate goal of having a home. For example, the boys tack out of the harbor and into the bay. A sailboat must tack if the wind is coming from the opposite direction in which it wants to travel: the boat must travels first in one direction about forty-five degrees away from its ultimate point of destination, and then turns ninety degrees and travels in that direction, turning back and forth between these two points. Thus, little by little and indirectly, the boat travels closer and closer to its destination, using the wind, which would blow them directly away from their destination, to its advantage. Similarly, Dicey, panicked and limited by time, decides in Wilmington to buy a ticket for Annapolis, taking them to the wrong side of the bay. Although they are not taking the most direct route, the trip to Annapolis indirectly draws them closer to their destination. Their journey is buttressed by the "winds" prevailing at that time, such as Dicey's concern about Eunice finding them, and the easy availability of the bus to Annapolis.
In fact, the Tillerman's entire journey is a form of tacking: they indirectly draw toward their ultimate destination. They stop first in Bridgeport, but find that this is only an intermediary destination, and they tack into the wind again, setting out for Crisfield and their grandmother. However, in the same way that Dicey begins to be seduced by the motion and constant changing of the waves as she sails across the Chesapeake, she becomes enamored with travel and rootlessness itself. She realizes, during her trip across the bay, that all of life is merely a series of intermediary destinations and that the only final destination is the grave. Thus, she begins to welcome change with open arms as part of the process of life and of moving toward an always-receding goal. The Tillerman's ultimate destination is an undefined home, but, as Dicey is beginning to realize, they are forging a home in each another through their travels. The lack of physical and social resources that necessitates their journey spawns a deep devotion to one another. Though they have not yet reached a resting place, they have already found a home.
Virtually all of the people who drift into Dicey's life come in pairs: Lou and Edie, Stew and Windy, Eunice and Father Joseph, Tom and Jerry, Claire and Will. In part, this pairing characterizes the book as a quest novel, or adventure/accomplishment romance, which tends to caricature peripheral characters and use them as metaphors or representatives of the challenges the protagonist is facing. Lou and Edie represent the dangers of self-indulgent rebellion and lawlessness, Stew and Windy represent generosity, integrity, and kindness, Eunice and Father Joseph represent false generosity, smallness, and excessive piety, Tom and Jerry represent harmless youthful rebellion, and Will and Claire represent the possibility of itinerancy as a way of life. The individuals who do not come in pairs, Momma and their grandmother, are much more complicated and pay for their individuality by rejecting or being rejected by society. The Tillermans, an uncomfortable foursome, move among these pairs and between these two individuals at either end of their journey, trying to establish themselves in relation to all these possibilities.