Toward the close of the summer of 1765 a party consisting of Major John Field, William Hill, one Slaughter, and two others, all from Culpeper County, Virginia, visited Boone and induced him to accompany them on the "long Journey" to Florida, whither they were attracted by the liberal offer of Colonel James Grant, governor of the eastern section, the Florida of to-day.

On this long and arduous expedition they suffered many hardships and endured many privations, found little game, and on one occasion narrowly escaped starvation.

They explored Florida from St.Augustine to Pensacola; and Boone, who relished fresh scenes and a new environment, purchased a house and lot in Pensacola in anticipation of removal thither.

But upon his return home, finding his wife unwilling to go, Boone once more turned his eager eye toward the West, that mysterious and alluring region beyond the great range, the fabled paradise of Kentucky.
The following year four young men from the Yadkin, Benjamin Cutbird, John Stewart (Boone's brother-in-law who afterwards accompanied him to Kentucky), John Baker, and James Ward made a remarkable journey to the westward, crossing the Appalachian mountain chain over some unknown route, and finally reaching the Mississippi.

The significance of the journey, in its bearing upon westward expansion, inheres in the fact that while for more than half a century the English traders from South Carolina had been winning their way to the Mississippi along the lower routes and Indian trails, this was the first party from either of the Carolinas, as far as is known, that ever reached the Mississippi by crossing the great mountain barrier.