The Columbia Expedition set sail from Boston Harbor on the morning of October 1, 1787, after a brief party with family and friends. The vessels reached the Cape Verde Islands on November 9, where Simeon Woodruff, after a dispute with Kendrick, left "Columbia" and went onto the islands with all his baggage. Kendrick was unhappy with the way "Columbia" handled, and felt that the hold had not been well packed, which Woodruff had been responsible for. When Kendrick ordered the hold broken up and repacked, Woodruff refused to help and after continued bickering Kendrick removed Woodruff from his position as first officer, after which Woodruff opted to leave the expedition entirely. A Spanish captain passing by the islands offered to take Woodruff to Madeira. He eventually returned to America and lived in Connecticut most of the remainder of his life.