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Thomas O. LeRoy's journal contains log entries, diary entries, and drawings that he composed while sailing onboard the merchant ship Natchez from New York to Valparaíso, Chile, and back to New York between September 1841 and May 1842. LeRoy recorded the ship's progress, his observations about seafaring life, the scenery he passed, his travels in Chile, and other topics.

Thomas O. LeRoy's journal contains approximately 85 pages of log and diary entries that he composed while sailing onboard the merchant ship Natchez from New York to Valparaíso, Chile, and back to New York between September 1841 and May 1842. Also included are 9 drawings he made on the voyage, an inventory of the belongings he carried during the trip, and 7 pages of double-entry bookkeeping accounts of Captain Robert Waterman of the brig Konohassett and of Theodore Lewis of the brig Philip Howe.

LeRoy began his journal with a brief entry on August 28, 1841, and the Natchez set sail under Captain Robert Waterman on September 1. Between September 1 and November 11, LeRoy regularly kept detailed log entries documenting the ship's course, winds, and notable onboard occurrences. The log entries were often interspersed with prose accounts of life on the Natchez, in which he mentioned seeing birds and aquatic animals, and described the scenery, particularly after the Natchez reached the Brazilian coast. In early November, LeRoy interrupted his log with detailed descriptions of the scenery around Tierra del Fuego, and he resumed his regular entries until reaching Valparaíso, Chile, on November 15.

LeRoy recorded his impressions of the Chilean people and discussed his travels around the country, which included visits to nearby towns and to Santiago. He noted other ships in the harbor, reconsidered his decision to embark on a seafaring life, and discussed sailors' religious beliefs. The Natchez began its return journey on February 6, 1842, and LeRoy continued to write journal entries about his experiences onboard, sometimes mentioning his eagerness to return to his family. After a brief stop at Pernambuco, Brazil, the ship sailed through the Caribbean and, at a point of about 160 miles from New York, LeRoy composed his final entry, dated May 1, 1842. The journal is followed by an inventory of the belongings LeRoy brought along on his trip. He dedicated the volume to Midshipman Charles Cooper of New York.

LeRoy drew 9 pencil sketches during his time on the Natchez.

• Cape Horn
• Juan Fernandez, "the Island where Robinson Crusoe resided"
• Huasco, Chile
• "Attack on fort Moultrie by the British"
• "Ship Natchez... in a snow squall"
• "View of the Brazil Coast near El Salvador with Negro Fishermans Hut on a small rocky Island"
• Cape St. Augustine, Brazil, and Saint Aleixo Island
• Brazilian coast near Pernambuco, with a view of a "Coca Nut Plantation"
• View of Brazil near Cape São Roque

The volume holds 7 pages of double-entry bookkeeping accounts. These record the finances of Theodore Lewis of the brig Philip Howe and those of Robert Waterman during a trip to Asia onboard the Konohassett.