What city lies approximately halfway between Miami and Havana, Cuba?

Perched at the southernmost tip of the continental United States, this island city marks the final stop on the scenic Overseas Highway from the Florida mainland. While not a perfect mathematical midpoint, its location is strategically and culturally significant. It sits approximately 105 miles north of the Cuban capital and about 160 miles southwest of Miami by road, making it the closest American city to Cuba and the essential waypoint between the two.

This proximity has defined the city's character for centuries. The connection is famously immortalized at the Southernmost Point buoy, a landmark that proudly proclaims it is just "90 Miles to Cuba." Long before it was a major tourist destination, the island was a hub for Cuban expatriates, who established a thriving cigar industry in the 19th century that made it Florida's wealthiest city. This deep historical and geographical link is still evident today in the island's architecture, cuisine, and vibrant, independent spirit.