The first American flag to flap over the Florida Keys had 13 stripes and 24 stars. This flag flew from 1822 to 1836.
While the first staff to fly an American flag was raised in Key West in March 1822, the second seems to have been planted in the Middle Keys at Port Monroe.
On Feb. 10, 1823 it was noted in a Notice to Mariners, “The public is informed that this settlement was commenced, Nov. 19, 1822 by Joshua Appleby of New Port, Rhode Island, and John W. Fiveash of Norfolk, Va. Immediately at the west of the Key (Vaca), which lies latitude 21, 41 N., is the settlement, which there is a flag staff erected.”
A third staff was raised at Indian Key some years later. Reflecting the idea that people in the Florida Keys need little reason to celebrate, the following observation was recorded in the Key West Register on April 6, 1829, regarding the installation of a flagpole. “The citizens of the Key were joined by a number of wreckers and smackmen and the staff was raised amidst the shouts of the multitude assembled on the occasion. A remarkable occurrence took place — persons who had climbed to the top of the staff, up to the height of 40 feet—after drinking several toasts, threw the glasses to the ground, which fell without breaking or fracturing any of them.”