Why go
The story explains why such a small island attracted merchants and naval attention. John W. Simonton bought a claim after John Whitehead described the harbor's potential. Another buyer contested the property, while a U.S. naval officer raised the flag in 1822. The island's position on the Florida Straits made the harbor strategically valuable.
The full story
In 1815, a Spanish official deeded Key West to Juan Pablo Salas. After Florida transferred to the United States, Salas sold claims to two buyers: John Geddes and John W. Simonton. Geddes challenged Simonton's ownership, but Simonton secured title. His friend John Whitehead had described the island's deep harbor after being stranded there by a shipwreck. The attraction was geographic as much as commercial. Key West sat beside the shipping passage through the Florida Straits, connecting the Atlantic Ocean and the Gulf of Mexico. In March 1822, Matthew C. Perry arrived aboard the schooner Shark and raised the U.S. flag. Perry briefly renamed the island Thompson's Island and its harbor Port Rodgers, names that did not displace Key West. The overlapping sale and naval claim show how private investment and federal strategy together shaped the town's beginning.
Useful to know
- Pair this history with the Old Town waterfront, where the harbor's strategic value is easiest to picture.