While the previous chapter ends hopefully, chapters fourteen and fifteen return to the tragic desperation of  Uncle Tom's situation. As the riverboat travels along the Mississippi River, Tom's kind-heartedness earns Haley’s trust. Haley unshackles Tom, allowing him to move around freely and even lend a hand to the boat crew with their tasks. Despite his circumstances, Tom remains devout and finds solace in reading his Bible, thinking fondly of his loved ones.

Aboard the boat, Tom encounters three interesting individuals: Augustine St. Clare, his five-year-old daughter, Eva, and his cousin from Vermont, Miss Ophelia. Eva is a stunning child with long golden-brown hair and an almost divine beauty; Tom instantly takes a liking to Eva, and the two quickly form a close bond. Eva promises Tom that her father will buy him, and when she falls overboard, Tom jumps in to save her.

St. Clare is a wealthy man from New Orleans with a haughty and sarcastic demeanor but agrees to negotiate with Haley to purchase Tom, playfully taunting the slave trader by pointing out that Tom's piety and intelligence should lower his price. Ultimately, the sale proves successful, and Tom is sold to St. Clare. As Tom grows closer to St. Clare, he learns more about the man’s past; St. Clare's father was a wealthy plantation owner in Louisiana, and his mother was a religious woman with strict morals. He fell in love with another woman but eventually married Marie, his current wife, due to a series of misunderstandings. St. Clare is deeply attached to Eva because she reminds him of his beloved mother, who has since passed away.

St. Clare’s cousin, Miss Ophelia is a forty-five-year-old unmarried woman from the New England branch of the St. Clare family. Known for her efficiency, sense of duty, and strong religious beliefs, she traveled to New Orleans with her cousin and niece to assist with running their household, as Marie is too unwell to manage it on her own.

Upon arriving in New Orleans, the group travels to the St. Clare mansion. They are greeted by Adolph, a haughty servant of St. Clare. The tranquility and beauty of the new surroundings stun Tom, but Adolph’s frosty reception brings him back to reality. When Eva embraced Mammy, one of the servants, and spoke to her affectionately, Miss Ophelia chided her, warning her against fraternizing with the servants. St. Clare greets his wife and tells her that Tom is to be her new coachman, but she dismissively predicts that he will be a useless drunk.