Why go
Understanding the island's shape helps you group stops sensibly. The historic streets and harbor lie to the west, while New Town and the airport are farther east. The Florida Straits run between Key West and Cuba, and the Overseas Highway traces the route that finally connected the island to mainland Florida by land.
The full story
Key West sits near the meeting of Atlantic and Gulf waters, with the Florida Straits stretching toward Cuba. The original settlement developed on the western end of the island. Landfill later enlarged the eastern side, now known as New Town. That distinction explains why the harbor and many historic sights cluster in Old Town while other everyday parts of the city lie farther east. For much of its history, reaching Key West meant arriving by water. Henry Flagler's Overseas Railway linked it to mainland Florida in 1912. A 1935 hurricane destroyed much of the rail line, and its route was rebuilt as a road, completed in 1938. The Overseas Highway remains the land connection through the Keys. The railway's loss also underlines a basic feature of this low island: severe storms can change travel conditions, so plans that depend on crossings and outdoor time need current weather information.
Useful to know
- Keep western Old Town sights together; allow a separate crossing for New Town or the airport.
- Check current weather and road conditions when a storm may affect travel through the Keys.