The island has been an important part of Florida folklore due to its connection to the pirate Gasparilla (José Gaspar), and it has been a significant tourist destination since the early 20th century.

In 1897 Albert W. Gilchrist, future governor of Florida, purchased land at Boca Grande and platted it for development as a town.

The folklore account does not appear in writing until about 1900 when it was included in an advertising brochure for the Charlotte Harbor and Northern Railway company.

[1] Afterward Gasparilla was an important stop for phosphate shipping, and it remained so until the dredging of the Port of Tampa in the 1970s.

In 1911, the first hotel, the Gasparilla Inn, opened, and the island became a major vacation destination for affluent people from Tampa and Fort Myers.