The Florida Keys form an archipelago extending 120 miles southwest from the southern tip of the Florida Peninsula, comprising approximately 1,700 islands of which fewer than 50 are inhabited. The chain begins at Key Largo, roughly 15 miles south of Miami, and terminates at the Dry Tortugas, 70 miles west of Key West. The Overseas Highway, designated U.S. Route 1, connects the inhabited islands across 42 bridges, the longest being the Seven Mile Bridge spanning the gap between Knight's Key and Little Duck Key. The highway replaced Henry Flagler's Overseas Railroad, completed in 1912 and destroyed by the 1935 Labor Day Hurricane, which remains the strongest hurricane to make landfall in Florida with sustained winds of 185 miles per hour. The Keys lie between the Atlantic Ocean to the east and the Gulf of Mexico to the west, separated from the mainland by Florida Bay. The geological foundation consists primarily of ancient coral reef deposits from the Pleistocene epoch, exposed during lower sea levels and now forming the fossilized limestone visible at many shorelines.
The Keys are divided informally into Upper Keys, Middle Keys, and Lower Keys, though no official boundary markers exist. Key Largo, the first and longest island at 33 miles, contains John Pennekamp Coral Reef State Park, established in 1963 as the first underwater park in the United States, covering 70 nautical square miles and extending three miles into the Atlantic. The reef system here forms part of the Florida Reef, the third-largest barrier reef system globally after the Great Barrier Reef and the Belize Barrier Reef, stretching 360 miles from the Dry Tortugas to Martin County. Islamorada, spanning six islands in the Upper Keys, calls itself the sport fishing capital of the world, a designation supported by International Game Fish Association records showing 98 world records set in local waters since 1939, primarily for tarpon, bonefish, and permit. Marathon, the commercial center of the Middle Keys with a year-round population of approximately 8,300 according to 2020 Census data, serves as the only municipality between Key Largo and Key West. The island contains the Crane Point Museum and Nature Center, which preserves a 63-acre hammock containing archaeological evidence of pre-Columbian occupation dating to 800 BCE, documented through midden deposits and pottery fragments analyzed by the Florida Museum of Natural History.
The Lower Keys begin at Big Pine Key, home to the National Key Deer Refuge established in 1957 to protect the Key deer, an endemic subspecies of white-tailed deer standing 24 to 32 inches at the shoulder and weighing 45 to 75 pounds at maturity. The U.S. Fish and Wildlife Service documented 1,017 individual deer in the 2021 population survey, up from a low of 27 animals in 1957 when the refuge was created. The species exists nowhere else on Earth, evolving through insular dwarfism over approximately 8,000 years following the last glacial maximum when rising sea levels isolated the Keys. The refuge encompasses 9,200 acres across multiple islands, with approximately 2,300 acres designated as critical habitat under the Endangered Species Act. Vehicle strikes remain the leading cause of mortality, accounting for 109 of the 128 recorded Key deer deaths in 2022 according to refuge records. The refuge requires vehicles to observe a 35 mile per hour speed limit on U.S. 1 through Big Pine Key and 25 miles per hour on side roads between sunset and sunrise.
Key West sits 90 miles north of Cuba and 106 miles southwest of Miami, occupying 4.2 square miles at the southernmost point of the continental United States, marked by a concrete buoy installed in 1983 at the corner of South Street and Whitehead Street claiming "90 Miles to Cuba" though the actual distance to the Cuban coast is 94 miles. The city's year-round population was 24,649 in the 2020 Census, down from 25,478 in 2010, while Monroe County, which encompasses the entire Keys, recorded 82,874 residents. The southernmost point marker photograph location requires waits exceeding one hour during peak cruise ship days, when up to 8,000 passengers arrive at the Outer Mole Pier and Mallory Square docks. Key West served as the wealthiest city per capita in the United States in 1890, enriched by wrecking operations that salvaged cargo from ships grounding on the reef. The city's wrecking industry peaked between 1830 and 1860, with wrecking licenses issued to 60 vessels in 1850 alone, generating court-authorized salvage awards totaling approximately $1.4 million annually in the 1850s, equivalent to roughly $45 million in 2024 dollars accounting for inflation.
The establishment of lighthouses along the reef, beginning with the Carysfort Reef Light in 1852, reduced groundings and effectively ended the wrecking economy by the 1870s. Key West pivoted to cigar manufacturing, with Cuban immigrant workers producing 100 million cigars annually by 1890 in more than 160 factories, making the city the cigar capital of the United States until labor disputes and a fire in 1886 shifted much of the industry to Tampa. The city's strategic position led to the establishment of Naval Air Station Key West in 1917, expanded significantly during World War II when the military presence exceeded 14,000 personnel, outnumbering civilians. The base continues operating as a naval air station and hosts TOPGUN training exercises, with F/A-18 Super Hornets conducting practice runs visible from shore. Truman Annex, originally part of the naval station, contained the Little White House where President Harry Truman spent 175 days during his presidency between 1946 and 1952, conducting official business including meetings leading to the creation of the Central Intelligence Agency and the Department of Defense. The building now operates as a museum maintaining the interior as it appeared during Truman's residency, with original furnishings including the poker table where he conducted informal cabinet meetings.
Key West's Old Town district contains the largest concentration of wooden frame buildings in Florida, with 3,500 structures pre-dating 1940 and more than 100 from the 19th century. The Historic District encompasses 140 blocks designated on the National Register of Historic Places in 1984. Architectural styles include Conch houses, vernacular structures built by Bahamian immigrants featuring horizontal board siding, metal roofs, wide porches, and elevated foundations designed for ventilation and flood protection. The term "Conch" originally referred to Bahamian immigrants who arrived beginning in the 1820s, named for the queen conch that formed a dietary staple. Modern usage applies "Conch" to anyone born in Key West. The Audubon House, built in 1840 by Captain John Geiger, a harbor pilot and wrecker, displays 28 original John James Audubon engravings from "The Birds of America" though Audubon himself never stayed in the building, spending three weeks in Key West in 1832 boarding elsewhere while cataloging birds for his publication.
The Ernest Hemingway Home and Museum occupies a Spanish Colonial house built in 1851 on Whitehead Street where Hemingway lived from 1931 to 1939, writing "Death in the Afternoon," "Green Hills of Africa," "To Have and Have Not," and portions of "For Whom the Bell Tolls." The property maintains descendants of Hemingway's original polydactyl cats, with approximately 50 cats residing on site, roughly half exhibiting the polydactyl trait of extra toes caused by a genetic mutation. Genetic testing conducted by the University of California, Davis in 2012 confirmed the current population descends from Snow White, a six-toed cat given to Hemingway by a ship's captain. The cats are registered with the U.S. Department of Agriculture and monitored by Monroe County Animal Control. A 2014 legal dispute reached the 11th Circuit Court of Appeals, which ruled the museum must obtain a USDA exhibitor's license and follow regulations because the cats substantially affect interstate commerce by attracting tourists.
Duval Street runs 1.25 miles from the Gulf of Mexico to the Atlantic Ocean, forming the commercial center with bars, restaurants, galleries, and shops occupying primarily 19th and early 20th-century structures. Sloppy Joe's Bar, opened at its current location at 201 Duval Street in 1937, claims association with Hemingway though historical records place his regular drinking at the original Sloppy Joe's at 428 Greene Street before the 1937 move, and at the Compleat Angler bar in the Havana-Madrid restaurant building. Captain Tony's Saloon occupies the original Sloppy Joe's location and contains a tree growing through the roof that reportedly served as a hanging tree in the 19th century, though no execution records from Monroe County confirm hangings at that specific location. The Green Parrot Bar, operating since 1890 at 601 Whitehead Street, maintains original cypress interior woodwork and a stamped tin ceiling installed in 1890.
Mallory Square hosts the nightly Sunset Celebration, a tradition formalized in the early 1960s when hippies and street performers began gathering at the docks. The celebration occurs daily year-round, weather permitting, beginning approximately two hours before sunset. Performers include jugglers, musicians, magicians, and trained animal acts, each paying a fee to the Sunset Celebration Association, a vendor organization managing performance spaces through a lottery system. The square occupies the site of the original Thompson's Fish House and Laundry, visible in 1890s photographs, demolished in the 1960s urban renewal program that destroyed much of the waterfront's historic commercial district.
The Key West Cemetery, established in 1847 after the 1846 hurricane destroyed the previous cemetery, contains 100,000 burials on 19 acres, exceeding the city's living population by a factor of four. Above-ground vaults predominate due to the high water table and shallow soil depth over limestone bedrock. Notable markers include "I Told You I Was Sick" on the grave of B.P. Roberts, who died in 1979, and a section dedicated to sailors from the USS Maine, whose sinking in Havana Harbor in 1898 precipitated the Spanish-American War. The cemetery contains a memorial to 61 Cuban immigrants who died when their vessel sank off Key West in 1899, identified in cemetery records as the "Cuban Burial Section."
Fort Zachary Taylor, completed in 1866 after 21 years of construction, protected Key West harbor through the Civil War, though Florida had seceded from the Union in 1861. Union forces held the fort throughout the war due to the prior presence of troops and the fort's strategic importance in maintaining the blockade of Southern ports. The fort's armament included two 15-inch Rodman guns, the largest coastal defense weapons manufactured by the Union, with each gun weighing 49,000 pounds and capable of firing a 450-pound solid shot 2,100 yards. Archaeological excavations between 1968 and 1972 uncovered more than 400 artifacts including cannonballs, rifles, and uniform buttons buried when the Army reduced the fort's profile in 1898 to protect it from plunging fire from modern rifled artillery. The fort became a state park in 1976 and contains the largest cache of Civil War armaments in the United States according to National Park Service documentation.
Fort Jefferson, occupying Garden Key in the Dry Tortugas 70 miles west of Key West, remains the largest masonry structure in the Western Hemisphere, comprising 16 million bricks in a hexagonal design with walls 50 feet high and 8 feet thick. Construction began in 1846 and continued through 1875 though the fort was never completed, abandoned as obsolete when rifled cannons demonstrated the ability to penetrate masonry fortifications during the Civil War. The fort served as a military prison from 1861 to 1874, housing approximately 2,000 Union deserters and Confederate prisoners. Dr. Samuel Mudd, convicted of conspiracy in the assassination of Abraham Lincoln for setting John Wilkes Booth's broken leg, served four years at Fort Jefferson from 1865 to 1869, receiving a pardon from President Andrew Johnson after treating soldiers during an 1867 yellow fever outbreak that killed 38 men. The fort became a national monument in 1935 and expanded to a national park in 1992, encompassing 100 square miles of which 99 percent is water.
Access to Dry Tortugas National Park requires a seaplane, ferry, or private boat, as no bridge connects the islands. The Yankee Freedom III catamaran departs Key West daily except during weather closures, completing the 70-mile crossing in approximately two hours and fifteen minutes. The park recorded 79,200 visitors in 2022 according to National Park Service statistics, with overnight camping permitted on Garden Key limited to 10 sites available first-come, first-served. The park's name derives from the abundance of sea turtles observed by Ponce de León during his 1513 expedition, who named the islands "Las Tortugas," with "Dry" added to later charts warning mariners of the absence of fresh water. The park protects nesting habitat for brown noddies, sooty terns, and magnificent frigatebirds, with approximately 100,000 sooty terns arriving annually between March and September to breed on Bush Key, adjacent to Garden Key. The terns are visible and audible from Fort Jefferson's ramparts during nesting season, creating what historical accounts described as "blackened skies" when the colony took flight.
Key West serves as the terminus for the Florida Keys Overseas Heritage Trail, a 106-mile paved path for bicycles and pedestrians utilizing portions of Flagler's railroad right-of-way and sections of the Overseas Highway. The trail remains incomplete, with 76 miles finished as of 2023 according to Florida Department of Transportation records, requiring riders to share roadway with vehicles for the remaining sections. The Seven Mile Bridge contains a parallel decommissioned bridge segment, the Old Seven Mile Bridge, closed to vehicles in 1982 but maintained as a fishing pier and pedestrian path extending 2.2 miles from Marathon before ending at Pigeon Key due to a removed section preventing continuous passage. Pigeon Key, a 5-acre island beneath the bridge, housed construction workers building the railroad bridge from 1908 to 1912, with workers' barracks, a mess hall, and superintendent's quarters remaining and operated as a museum accessible by ferry or by walking the old bridge from Marathon.
Conch fritters, deep-fried dough balls containing chopped queen conch meat, bell peppers, and celery, appear on restaurant menus throughout the Keys, though commercial harvest of queen conch has been prohibited in Florida waters since 1985 due to overfishing that reduced the population by 80 percent between 1950 and 1975. Restaurants import conch from the Bahamas, Turks and Caicos, or Caribbean nations where limited harvest continues under management plans. Key lime pie, designated the official pie of Florida by the state legislature in 2006, originated in the Keys using the small, yellow Key lime, a citrus variety named Citrus aurantifolia, distinct from the larger Persian lime that dominates commercial cultivation. Authentic Key lime pie contains Key lime juice, condensed milk, and egg yolks in a graham cracker or pastry crust, traditionally topped with meringue though whipped cream has become common. The dessert's invention is undocumented, with competing claims from multiple Keys families in the late 19th or early 20th century, and no definitive attribution. Key limes grow on thorny trees reaching 15 feet tall, producing fruit year-round with peak harvest from June through September. The trees exhibit intolerance to cold, with significant damage occurring at temperatures below 32 degrees Fahrenheit, limiting commercial cultivation to the southernmost areas of Florida and requiring replacement after periodic freeze events.
Stone crab claws, harvested from October 15 through May 15, come from the Florida stone crab, a species inhabiting waters from North Carolina through the Gulf of Mexico but harvested commercially almost exclusively in Florida waters. State regulations require harvesting only the claws, which must measure at least 2.75 inches in the propodus, the largest section of the claw, measured from the elbow to the tip. Fishers remove one or both claws and return the crab to the water alive, with claws regenerating over multiple molts requiring 18 to 24 months to reach harvestable size again. Florida Fish and Wildlife Conservation Commission studies show 73 percent survival rates for properly declawed crabs returned immediately to water. Joe's Stone Crab in Miami Beach, opened in 1913, developed the commercial market for stone crab claws, previously discarded by commercial fishers targeting the meat-filled body. Monroe County waters produce approximately 60 percent of Florida's stone crab harvest, with 484,000 pounds landed in the 2021-2022 season from Monroe County alone according to Florida Fish and Wildlife data, compared to 805,000 pounds statewide.