True to his word, Lincoln's party departed from Arsenal dock, at the 6th Street wharf in Washington at 1 p.m. His party consisted of Mrs. Lincoln, her maid, Lincoln's son Tad, bodyguard W. H. Crook, and Captain Charles B. Penrose who was assigned to travel with the group by Secretary of War Edwin Stanton. (I've checked a number of sources to see if the maid was Elizabeth Keckley, but have been unsuccessful in confirming this.) Even though he had been ill for several days, Secretary Stanton left his sick bed and took a carriage to see the President off, even though Stanton's wife Ellen protested his doing so.

After the presidential party left, Stanton became concerned because an hour after they departed a very strong wind blew over Washington. The Washington Herald described the storm as follows: "The terrific squalls of winds, accompanied by thunder and lightning, did considerable damage here. The roof of a factory on Sixth street was blown off into the street and fell upon a hack, crushing the horses and its driver." Trees were blown over in some neighborhoods and the winds played havoc with some of the boats, which, the Herald reports, "were dashed about with great violence."
Ever the worry wort, Stanton was frantically worried about the President's boat. Ay 8:45 p.m. he sent a telegraph to Lincoln, stating "I hope you have Point Lookout safely notwithstanding the furious gale that came on soon after you started. Please let me hear from you at Point Lookout."
Stanton needn't have worried. According to Doris Kearns Goodwin in Team of Rivals at pages 708-9:
Lincoln was enjoying himself immensely. While Tad raced around the ship, investigating every nook and befriending members of the crew, Lincoln remained on deck, watching "the city until he could see it no more." Once inside, he listened with relish to the adventures of the River Queen's captain, who had chased blockade runners early in the war. "It was nearly midnight when he went to bed," Crook recalled.
Crook, who shared a stateroom with Tad, was "startled out of a sound sleep" by Mary Lincoln. "It is growing colder," she explained, "and I came to see if my little boy has covers enough on him." Later that night, Crook was awakened by the steamer passing through rough waters, which felt as if it were "slowly climbing up one side of a hill and then rushing down the other." The next morning, feeling seasick, Crook noted that the turbulent passage had apparently not disturbed Lincoln. On the contrary, the President looked rested, claimed to be "feeling splendidly," and did "full justice to the delicious fish" served at breakfast.
Mary would nostalgically recall her husband's fine humor during this last trip to City Point. "Feeling so encouraged" the war "was near its close," and relieved from the daily burdens of his office, "he freely gave vent to his cheerfulness," to such an extent that "he was almost boyish in his mirth & reminded me of his original nature, which I had always remembered of him in our home - free from care, surrounded by those he loved so well."
