Mrs. R. W. Benson lived in or near Pawtucket, R. I., and was probably a widow in her late fifties or early sixties when she embarked on a trip to Florida. On December 11, 1905, she left the Pawtucket railway station in the company of "Cousin" Abner, his sister Lydia, and Anna Johnson, a "jolly, hearty Swede of 45 or 50," who served as housekeeper. On the way to Florida they were joined by Gamaliel Bradford Draper (identified as "brother," aged 74), and William Bradford Draper (identified as "nephew," aged 21, and later nicknamed "Saving Grace"). Although they are all probably related, the precise relationships are difficult to determine.
Abner apparently owned a house and some property in Thonotosassa, a town about sixteen miles from Tampa. Mrs. Atwood, another potential relation, had a house nearby. Two other neighbors who were also there that winter, the Adamses and Elliots, who owned a total of 160 acres that they had laid claim to in 1877.
Mrs. Benson noticed the land and the "colored people" she passed by on her way, often focusing on the size and condition of the homes she observed from the train. Once in Tampa, the party stopped at the Steacy's Hotel, where Lydia rested while the others visited Palmetto Beach, the post office, and the Tampa Bay Hotel, "said to be the largest and most beautiful in the world." That evening they took the short train ride to Thonotosassa, where neighborly Mr. Adams met them with his carriage and drove them the remaining two miles to the house, which a "dignified colored woman" had prepared for their arrival.
While at Abner's house, Mrs. Benson cared for and worried about Lydia, who had pushed herself too hard on the trip down, and subsequently spent much of her time dozing and overeating. Mrs. Benson frequently did get out of the house, walking to the store with "Swedish Anna," visiting her neighbor, Mrs. Adams, and taking carriage rides. A rumor of 75 cases of smallpox in Tampa might have been a strong disincentive to returning to the city. Abner, on the other hand, spent a good deal of time "on business" in Tampa, which included acquiring a horse that promptly fell sick with distemper upon arrival in Thonotosassa.