Key West is closer to Cuba than Miami. As it's famously stated on the Southernmost Buoy at the end of Simonton Street, Key West is 90 miles to Cuba. But to get to Key West from Miami, it's a 150-mile drive down the Overseas Highway.

Geographically, Key West is significantly closer to mainland Florida than it is to Cuba. Key West is approximately 15 to 20 miles away from the nearest uninhabited keys that are part of the Florida mainland's contiguous coastal ecosystem, and it is about 129 miles from the city of Miami by car via the Overseas Highway. In contrast, the famous "Southernmost Point" buoy in Key West famously claims it is "90 miles to Cuba," though the actual shortest distance to the Cuban coast is approximately 94 to 96 miles. While it is true that Havana is closer to Key West (about 105 miles) than many major Florida cities are, the island remains a political and physical extension of the Florida archipelago. Due to the curvature of the Earth, you cannot actually see Cuba from Key West, despite many legends suggesting you can see the lights of Havana on a clear night.