He then went on to serve on on voyage about the Mediterranean which last two years. Cumberland was a ship that he would later fight against as a Confederate officer in the American Civil War. After returning to Annapolis, Maryland in September 1855, he received promotion to lieutenant. Wood returned to Maryland and met Lola Mackubin, daughter of a prominent Maryland politician. They were married on November 26, 1856. Their daughter, Anne, was born on September 18, 1857. In 1858 he served as a gunnery officer for eighteen months aboard . His infant daughter died in 1859 while he was in service. Civil War Lieutenant Wood taught gunnery tactics at the U.S. Naval Academy in Annapolis, at the beginning of the Civil War. Due to his southern sympathies, he resigned his commission on April 2, 1861, and took up farming nearby. He later went to Virginia and in October 1861, received a commission as a Confederate Navy first lieutenant, where he was appointed as officer in the Confederate States Navy by October and assigned to in November. Following service with shore batteries on the Potomac River, he became an officer in the newly converted ironclad CSS Virginia serving under Commander Buchanan. He was wounded in the Battle of Hampton Roads. Wood commanded the stern pivot gun during the battle and fired the shot that seriously wounded Lieutenant John Lorimer Worden, captain of Monitor. In May 1862, after Virginia was destroyed, Wood assisted with the defense of Drewry's Bluff, on the James River. During the next two years, Wood led several successful raids against Federal ships and also served as naval aide to Confederate President Jefferson Davis. Promoted to commander in May 1863, he simultaneously held the rank of colonel in the cavalry. These dual ranks, with his reputation for extraordinary daring and his family connections to Confederate leaders, allowed him to play an important liaison role between the South's army, navy and civil government. In August 1864, Wood commanded , a Confederate commerce raider and blockade runner against U.S. shipping off the Atlantic coast, capturing an astonishing 33 Union ships during a ten-day period off the coast of New England. He received the rank of captain in February 1865. A few months later, as the Confederacy was disintegrating, he accompanied President Davis in his attempt to evade capture and leave the country. Though briefly taken prisoner, Wood escaped to Cuba.