Now in her late teens and early 20s, Florence began teaching art to residents of Whitby. The Whitby Chronicle tells us in 1886 that her classes in oils, watercolours, and China painting took place at the Women's Canadian Temperance Union's free reading rooms in the Oddfellows building located on Brock St. During this time, she joined the Women's Art Association of Canada and travelled to Toronto for lessons at the Toronto Art School and with the Ontario Society of Artists. One of Florence's most important mentors and teachers was Lucius O'Brien, president of the Ontario Society of Artists and the Royal Canadian Academy of Artists. By this time, she was very much invovled in the early art scene of Toronto, showing artwork at a variety of exhibitions in the city. She became a member of the Ontario Society of Artists and the Royal Canadian Academy of Arts.

In 1892, Florence accepted a job as art instructor at Pickering College, a position she would hold until 1905. Around 1900, she became assistant art instructor at Ontario Ladies' College in Whitby. She maintained contact throughout her life with many of her students, including Rosa Clark (founder and owner of the Guild Inn) and artist Norma Wright Cotter.

Sometime in the early 1900s, Florence bought a house on the corner of Gilbert St. and Byron St. S. with her mother and sister, Mary. The house (pictured above), known as Gillebreathe, was the location of Florence's Whitby studio and classroom. In between teaching at her studio and Ontario Ladies' College, Florence took time to travel and focus on her own art. She resigned from Ontario Ladies' College in 1912 and turned Gillebreathe into a recital studio for concerts and examinations for students from Ontario Ladies' College.

The 1910s and 1920s were Florence's most prolific. In 1913, she landed in Paris where she enrolled in classes at the Académie de la Grande Chaumière, a Left Bank studio known for its aversion to strict adherance to the formal rules of art education. Later that year she exhibited her work in the Société Nationale des Beaux-Arts and was elected president of the British and American International Art Union. She continued to show her art at exhibits in Ottawa, Montreal, and Toronto and she travelled the United Kingdom, Europe, and North and South America to gain inspiration for her art.