She was a student and collaborator of botanist and geologist Nathaniel Lord Britton, with whom she helped to found the New York Botanical Garden.

Anna was born in New York's east side, the first child of David Olyphant Vail and Cornelia Georgina (Nina) Van Rensselear.

[citation needed] David O. Vail is listed as a "merchant" on an 1862 ship manifest[3] and in a Van Rensselaer family history is described as "...resident partner of the house of Olyphant & Company at Shanghai, China.

[8] In 1903, Vail traveled to Paris, France, for an auction of the botanical literature of the late Professor Claude Thomas Alexis Jordan.

[9] Vail wrote on numerous botanical topics; for example, her 1898 co-authored work (with Elizabeth Gertrude Britton, among others), details "New or Rare Mosses," such as Anacamptodon Splachnoides.

However, this account is disputed by a letter in the files of Nathaniel Lord Britton dated September 28, 1907, which mentions her departure as being due to an extended separation from her mother, who was living in France.