In 1890, Hall left for Europe and became Charles Winslow Hall. Charles participated in shooting contests and won several. He was a frequent gambler and drinker. He was a water-color painter.
In 1897 he met Guisseppa Boriani, also an artist, of Milan. They later married.
In 1901, Mr and Mrs Hall boarded the Città di Torina, bound for New York after receiving word that his father was dying. They occupied a luxurious stateroom on the upper deck. Mrs Hall spend time in the ladies’ parlour, while Charles drank, smoked and gambled with the men until he became ill from complications due to alcoholism. The ship’s doctors discovered that he was female-bodied, and informed the captain.
Mr Hall died en voyage, and as the ship docked, the story of Caroline Hall and her wife was featured in newspapers across the US. John Hall claimed the body, and there was a small family funeral. Ms Boriani was not considered family, but was still invited.
- “BOSTON WOMAN POSED AS MAN WITH A WIFE; Sex of Liner's Passenger Revealed Through Fatal Sickness. HAD LIVED TEN YEARS IN ITALY An Artist and Had Won Prizes In Shooting Contests -- said to be Daughter of Col. Hall, U.S.A., Retired.”. The New York Times, Oct 1, 1901. Online
- Havelock Ellis. Sexual Inversion. In Studies In The Psychology Of Sex. Random House. 1936: 247.
- The History Project. Improper Bostonians. Beacon Press, 1998: 104-5.
- “Caroline Hall”. Gay History Wiki. http://gayhistory.wikidot.com/caroline-hall.