William P. Clyde organized the company in 1874 and acquired various ships including the steamboat Beverly, Bristol, Philadelphia, Alliance, A.C. Stimers (likely named for Alban C. Stimers), May Flower, Ann Eliza (perhaps named for Ann Eliza Young) and the canal boats City of Buffalo and Catherine Moan.

In 1902, the company advertised tri-weekly sailings from Jacksonville to New York with a stop in Charleston, South Carolina as well as its St. Johns River line with the City of Jacksonville and routes to Providence and Boston, also stopping in Charleston.

[4] Captains with the line included Augustus Chelton and David Kemp.

[5] In 1926 the S.S. City of Jacksonville served a Christmas dinner that included pickled peaches, Indian relish, fruit fritters, macaroni au gratin, as well as turkey and cranberry sauce and desserts such as fruit cake and pumpkin pie, followed by a demitasse coffee.

[6] The Whitney family sold its Metropolitan Steamship Company business to Charles W. Morse in 1906.