Key West Island: largest island in city of Key West, Florida
|Area||5.27 sq mi (13.65 km2)|
|Length||4 mi (6 km)|
|Width||2 mi (3 km)|
|Highest elevation||18 ft (5.5 m)|
|Highest point||Solares Hill|
|Wikivoyage has travel information related to: Key West|
The island is about 4 miles (6.4 km) long and 2 miles (3.2 km) wide. In the late 1950s, many of the large salt ponds on the eastern side were filled in, nearly doubling the original land mass of the island. The island is 3,370 acres (13.6 km2) in area.
In Pre-Columbian times Key West was inhabited by the Calusa people. The first European to visit was Juan Ponce de León in 1521. As Florida became a Spanish colony, a fishing and salvage village with a small garrison was established here.
Cayo Hueso 
Cayo Hueso (Spanish pronunciation: [ˈkaʝo ˈweso]) is the original Spanish name for the island of Key West. Spanish-speaking people today also use the term Cayo Hueso when referring to Key West. It literally means "Bone Island" or "Bone Cay" (a low-lying island). It is said that the island was littered with the remains (bones) from a Native American battlefield or burial ground. The most widely accepted theory of how the name changed to Key West is that it is a false-friend anglicization of the word, on the ground that the word hueso [ˈweso]) sounds like "west" in English. Other theories of how the island was named are that the name indicated that it was the westernmost Key, or that the island was the westernmost Key with a reliable supply of water.
Many businesses on the island use the name, such as Casa Cayo Hueso, Cayo Hueso Resorts, Cayo Hueso Consultants, Cayo Hueso y Habana Historeum, etc.
In 1763, when the Kingdom of Great Britain took control of Florida, the community of Spaniards and Native Americans were moved to Havana. Florida returned to Spanish control 20 years later, but there was no official resettlement of the island. Informally the island was used by fishermen from Cuba and from the British Bahamas, who were later joined by others from the United States after the latter nation's independence. While claimed by Spain, no nation exercised de facto control over the community there for some time.
Matthew C. Perry and the opening of "Thompson's Island" 
In 1815, the Spanish governor in Havana, Cuba, deeded the island of Key West to Juan Pablo Salas, an officer of the Royal Spanish Navy Artillery posted in St. Augustine, Florida. After Florida was transferred to the United States, Salas was so eager to sell the island that he sold it twice – first for a sloop valued at $575, and then to U.S. businessman John W. Simonton, during a meeting in a Havana café, for the equivalent of $2,000 in pesos in 1821. The sloop trader quickly sold the island to a General John Geddes, a former governor of South Carolina, who tried in vain to secure his rights to the property before Simonton, with the aid of some influential friends in Washington, was able to gain clear title to the island. Simonton had wide-ranging business interests in Mobile, Alabama. He bought the island because a friend, John Whitehead, had drawn his attention to the opportunities presented by the island's strategic location. John Whitehead had been stranded in Key West after a shipwreck in 1819 and he had been impressed by the potential offered by the deep harbor of the island. The island was indeed considered the "Gibraltar of the West" because of its strategic location on the 90-mile (140 km)–wide deep shipping lane, the Straits of Florida, between the Atlantic Ocean and the Gulf of Mexico. On March 25, 1822, Matthew C. Perry sailed the schooner USS Shark (1821) to Key West and planted the U.S flag, physically claiming the Keys as United States property. Perry reported on piracy problems in the Caribbean. Perry renamed Cayo Hueso (Key West) to "Thompson's Island" for the Secretary of the Navy, Smith Thompson, and the harbor "Port Rodgers" for War of 1812 hero John Rodgers. Neither name was to stick. In 1823 Commodore David Porter of the United States Navy West Indies Anti-Pirate Squadron took charge of Key West, which he ruled (but, according to some, exceeding his authority) as military dictator under martial law.
First developers 
Soon after his purchase, Simonton subdivided the island into plots and sold three undivided quarters of each plot to:
- John Mountain and U.S. Consul John Warner, who quickly resold their quarter to Pardon C. Greene, who took up residence on the island
- John Whitehead, his friend who had advised him to buy Key West
- John Flemming (nowadays spelled Fleming)
John Simonton spent the winter in Key West and the summer in Washington, where he lobbied hard for the development of the island and to establish a naval base on the island, both to take advantage of the island's strategic location and to bring law and order to the town. He died in 1854.
Pardon C. Greene is the only one of the four "founding fathers" to establish himself permanently on the island, where he became quite prominent as head of P.C. Greene and Company. He also served briefly as mayor. He died in 1838 at the age of 57.
John Whitehead lived in Key West for only eight years. He became a partner in the firm of P.C. Greene and Company from 1824 to 1827. A lifelong bachelor, he left the island for good in 1832. He came back only once, during the Civil War in 1861, and died the next year.
John W.C. Flemming was English-born and was active in mercantile business in Mobile, Alabama, where he befriended John Simonton. Flemming spent only a few months in Key West in 1822 and left for Massachusetts, where he married. He returned to Key West in 1832 with the intention of developing salt manufacturing on the island but died the same year at the young age of 51.
The names of the four "founding fathers" of modern Key West were given to main arteries of the island when it was first platted in 1829 by William Adee Whitehead, John Whitehead's younger brother. That first plat and the names used remained mostly intact and are still in use today. Duval Street, the island's main street, is named after Florida's first territorial governor, who served between 1822 and 1834 as the longest serving governor in Florida's U.S. history.
William Whitehead became chief editorial writer for the Enquirer, a local newspaper, in 1834. He had the foresight to preserve copies of his newspaper as well as copies from the Key West Gazette, its predecessor. He later sent those copies to the Monroe County clerk for preservation, which gives us a precious view of life in Key West in the early days (1820–1840).
Many of the residents of Key West were immigrants from the Bahamas, known as Conchs (pronounced 'conks'), who arrived in increasing numbers after 1830. Many were descendants of Loyalists who fled to the nearest Crown colony during the American Revolution. In the 20th century many residents of Key West started referring to themselves as "Conchs", and the term is now generally applied to all residents of Key West. Some residents use the term "Conch" to refer to a person born in Key West, while the term "Freshwater Conch" refers to a resident not born in Key West but who has lived in Key West for seven years or more. However, the true original meaning of Conch applies only to someone with European ancestry who immigrated from the Bahamas.
Major industries in Key West in the early 19th century included fishing, salt production, and salvage. In 1860 wrecking made Key West the largest and richest city in Florida and the wealthiest town per capita in the U.S. A number of the inhabitants worked salvaging shipwrecks from nearby Florida reefs, and the town was noted for the unusually high concentration of fine furniture and chandeliers that the locals used in their own homes after salvaging them from wrecks.
U.S. Civil War 
While Florida seceded and joined the Confederate States of America during the American Civil War, Key West remained in Union hands because of the naval base. However, most locals were sympathetic to the South, and many flew Confederate flags over their homes. Fort Zachary Taylor, constructed from 1845 to 1866, was an important Key West outpost during the Civil War. Construction began in 1861 on two other forts, East and West Martello Towers, which served as side armories and batteries for the larger fort. When completed, they were connected to Fort Taylor by railroad tracks for movement of munitions. Fort Jefferson, located about 68 miles (109 km) from Key West on Garden Key in the Dry Tortugas, served after the Civil War as the prison for Dr. Samuel A. Mudd, convicted of conspiracy for setting the broken leg of John Wilkes Booth, the assassin of President Abraham Lincoln.
In the late 19th century, salt and salvage declined as industries, but Key West gained a thriving cigar-making industry.
By 1889 Key West was the largest and wealthiest city in Florida.
Overseas by rail and road 
Key West was relatively isolated until 1912, when it was connected to the Florida mainland via the Overseas Railway extension of Henry M. Flagler's Florida East Coast Railway (FEC). Flagler created a landfill at Trumbo Point for his railyards. The Labor Day Hurricane of 1935 destroyed much of the railroad and killed hundreds of residents, including around 400 World War I veterans who were living in camps and working on federal road and mosquito control projects in the Middle Keys. The FEC could not afford to restore the railroad.
The U.S. government then rebuilt the rail route as a highway, completed in 1938, which became an extension of United States Highway 1. The portion of U.S. 1 through the Keys is called the Overseas Highway. Franklin Roosevelt toured the road in 1939.
Winter White House 
Key West was in a down cycle when Franklin D. Roosevelt visited in 1939. The buildup of military bases on the island occurred shortly thereafter.
In addition to Truman, Dwight D. Eisenhower stayed in Key West following a heart attack. In November 1962, John F. Kennedy visited Key West a month after the resolution of the Cuban Missile Crisis. Jimmy Carter held a family reunion in Key West after leaving office.
Ernest Hemingway 
Legend has it that Ernest Hemingway wrote A Farewell to Arms while living above the showroom of a Key West Ford dealership at 314 Simonton Street  while awaiting delivery of a Ford Model A roadster purchased by the uncle of his wife Pauline in 1928.
Hardware store owner Charles Thompson introduced him to deep-sea fishing. Among the group who went fishing was Joe Russell (also known as Sloppy Joe). Russell was reportedly the model for Freddy in To Have and Have Not. Portions of the original manuscript were found at Sloppy Joe's Bar after his death. The group had nicknames for each other, and Hemingway wound up with "Papa".
Pauline's rich uncle Gus Pfeiffer bought the 907 Whitehead Street house  in 1931 as a wedding present. Legend says the Hemingways installed a swimming pool for $20,000 in the late 1930s (equivalent in 2013 to $330,000). It was such a high price that Hemingway is said to have put a penny in the concrete, saying, "Here, take the last penny I've got!" The penny is still there.
During his stay he wrote or worked on Death in the Afternoon, For Whom the Bell Tolls, The Snows of Kilimanjaro, and The Short Happy Life of Francis Macomber. He used Depression-era Key West as the locale for To Have and Have Not — his only novel set in the United States.
Pauline and Hemingway divorced in 1939; Hemingway only occasionally visited when returning from Havana until his suicide in 1961.
The six- or seven-toed polydactyl cats descended from Hemingway's original pet 'Snowball' still live on the grounds and are cared for at the Hemingway House, despite complaints by the U.S. Department of Agriculture that they are not kept free from visitor contact, and the Key West City Commission exempted the house from a law prohibiting more than four domestic animals per household.
Tennessee Williams 
Tennessee Williams first became a regular visitor to Key West in 1941 and is said to have written the first draft of A Streetcar Named Desire while staying in 1947 at the La Concha Hotel. He bought a permanent house in 1949 and listed Key West as his primary residence until his death in 1983. In contrast to Hemingway's grand house in Old Town, the Williams home at 1431 Duncan Street  in the "unfashionable" New Town neighborhood is a very modest bungalow. The house is privately owned and not open to the public. The Academy Award–winning film version of his play The Rose Tattoo was shot on the island in 1956. The Tennessee Williams Theatre is located on the campus of Florida Keys Community College on Stock Island. 
Williams had a series of rented homes all over the United States, but the only home he owned was in Key West.
Even though Hemingway and Williams were in Key West at the same time, they reportedly met only once—at Hemingway's Cuba home Finca Vigía.
Cuban presence 
In 1890, Key West had a population of nearly 18,800 and was the biggest and richest city in Florida. Half the residents were said to be of Cuban origin, and Key West regularly had Cuban mayors, including Carlos Manuel de Céspedes, son of the father of the Cuban Republic, who was elected mayor in 1876. Cubans were actively involved in reportedly 200 factories in town, producing 100 million cigars annually. José Martí made several visits to seek recruits for Cuban independence starting in 1891 and founded the Cuban Revolutionary Party during his visits to Key West.
The Battleship USS Maine (ACR-1) sailed from Key West on its fateful visit to Havana, where it exploded, igniting the Spanish-American War. Crewmen from the ship are buried in Key West, and the Navy investigation into the blast occurred at the Key West Customs House.
Pan American Airlines was founded in Key West, originally to fly visitors to Havana, in 1926.
John F. Kennedy was to use the U.S. distance "90 miles from Cuba" extensively in his speeches against Fidel Castro. Kennedy himself visited Key West a month after the resolution of the Cuban Missile Crisis.
Prior to the Cuban revolution of 1959, there were regular ferry and airplane services between Key West and Havana.
Key West was flooded with refugees during the Mariel Boatlift. Refugees continued to come ashore and, on at least one occasion, most notably in April 2003, flew hijacked Cuban Airlines planes into the city's airport. .
Key West was always an important military post, since it sits at the northern edge of the deepwater channel connecting the Atlantic and the Gulf of Mexico (the southern edge 90 miles (140 km) away is Cuba) via the Florida Straits. Because of this, Key West since the 1820s had been dubbed the "Gibraltar of the West." Fort Taylor was initially built on the island. The Navy added a small base from which the USS Maine (ACR-1) sailed to its demise in Havana at the beginning of the Spanish-American War.
At the beginning of World War II the Navy increased its presence from 50 acres (200,000 m2) to 3,000 acres (12 km²), including all of Boca Chica Key's 1,700 acres (7 km2) and the construction of Fleming Key from landfill. The Navy built the first water pipeline extending the length of the keys, bringing fresh water from the mainland to supply its bases. At its peak 15,000 military personnel and 3,400 civilians were at the base. Included in the base are:
- NAS Key West - This is the main facility on Boca Chica, where the Navy trains its pilots. Staff are housed at Sigsbee Park. In 2006 there were 1,650 active-duty personnel; 2,507 family members; 35 Reserve members; and 1,312 civilians listed at the base. In the 1990s the Navy worked out an agreement with the National Park Service to stop sonic booms near Fort Jefferson in the Dry Tortugas. Many of the training missions are directed at the Marquesas "Patricia" Target 29 nautical miles (54 km) due west of the base. The target is a grounded ship hulk 306 feet (93 m) in length that is visible only at low tide. Bombs are not actually dropped on the target.
- Truman Annex - The area next to Fort Taylor became a submarine pen and was used for the Fleet Sonar School. President Harry S. Truman was to make the commandant's house his winter White House. The Fort Taylor Annex was later renamed the Truman Annex. This portion has largely been decommissioned and turned over to private developers and the city of Key West. However, there are still a few government offices there, including the new NOAA Hurricane Forecasting Center. The Navy still owns its piers.
- Trumbo Annex - The docking area on what had been the railroad yard for Flagler's Overseas Railroad is now used by the Coast Guard.
Port of Key West 
In 1984 the city opened a pier right on Mallory Square. The decision was met with considerable opposition from people who felt it would disrupt the tradition of watching the sunset at Mallory Square.
Cruise ships now dock at all three piers.
Cruise Ship Statistics for 1994
- Number of visits: 368
- Passenger count: 398,370
- City revenues from docking charges: $852,887
Geography and climate 
According to the United States Census Bureau, the city has a total area of 7.4 square miles (19.2 km²), of which 5.9 square miles (15.4 km²) is land and 1.5 square miles (3.8 km²) (19.73%) is water.
Old Town/New Town 
Old Town 
The original Key West neighborhood in the west (although perceived as south) is called "Old Town" and comprises the Key West Historic District. It includes the major tourist destinations of the island, including Mallory Square, Duval Street, the Truman Annex and Fort Zachary Taylor. It is where the classic bungalows and guest mansions are found.
Generally, the structures date from 1886 to 1912. The basic features that distinguish the local architecture include wood-frame construction of one- to two-and-a-half-story structures set on foundation piers about three feet above the ground. Exterior characteristics of the buildings are peaked "metal" roofs, horizontal wood siding, gingerbread trim, pastel shades of paint, side-hinged louvered shutters, covered porches (or balconies, galleries, or verandas) along the fronts of the structures, and wood lattice screens covering the area elevated by the piers.
New Town 
The island has more than doubled in size via landfill. The new section on the east (perceived as north) is called "New Town." It contains shopping centers, retail malls, residential areas, schools, ball parks, and Key West International Airport.
According to the Key West Association of Realtors (KWAR), Key West can be divided into four distinct areas: Old Town, Casa Marina, Mid-Town and New Town, with various neighborhoods in each area.
Gulf of Mexico/Atlantic 
Key West and most of the rest of the Keys are on the dividing line between the Atlantic Ocean and the Gulf of Mexico. The two bodies have different currents, with the calmer and warmer Gulf of Mexico being characterized by great clumps of seagrass. The area where the two bodies merge between Key West and Cuba is called the Straits of Florida.
Southernmost City 
One of the biggest attractions on the island is a concrete replica of a buoy at the corner of South and Whitehead Streets that claims to be the southernmost point in the contiguous 48 states (see Extreme Points for more information.) The point was originally just marked with a sign, which was often stolen. In response to this, the city of Key West erected the now famous monument in 1983. Brightly painted and labeled "SOUTHERNMOST POINT CONTINENTAL U.S.A.", it is one of the most visited and photographed attractions in Key West. Land on the Truman Annex property just west of the buoy is the southernmost point of Key West, but still not the southernmost point of the continental US, and it has no marker since it is U.S. Navy land and cannot be entered by civilian tourists. The private yards directly to the east of the buoy and the beach areas of Truman Annex and Fort Zachary Taylor Historic State Park also lie farther south than the buoy. The farthest-south location that the public can visit is the beach at the state park for a small entrance fee. Florida's true southernmost point is Ballast Key, a privately owned island just south and west of Key West. Signs on the island strictly prohibit unauthorized visitors. The claim "90 Miles to Cuba" on the monument is not precise, as Cuba at its closest point is 94 statute miles from Key West. Further south than the southernmost point of Florida lie all the major islands of Hawaii as well as US territories, with two (American Samoa and Jarvis Island) actually in the Southern Hemisphere.
Frost-free zone 
Key West has an AW tropical savanna climate (Köppen), similar to the Caribbean islands. With the exception of cities right in the coast of South Florida (like Miami Beach) - Key West is the only city on the USA mainland to never record a frost. Key West is also one of the sunniest cities in the USA.
Like most tropical climates, the difference between the warmest and coldest months are small in Key West. The mean July temperature is 84 F (29 C) and the mean January temperature is 70 F (21 C). Low temperatures rarely drop below 55 °F (13 °C). The coldest temperatures ever recorded in Key West was 41 °F (5 °C) on January 12, 1886, and on January 13, 1981. Prevailing easterly tradewinds and sea breezes suppress the usual summertime heating. The average low and high temperatures in July are 79.6 °F (26.4 °C) and 89.4 °F (31.9 °C). There are 48 days per year with 90 °F (32.2 °C) or greater highs. The hottest temperature ever recorded in Key West is 100 °F (38 °C) in June, 1880, July 1880 and in August, 1880. Water temperatures average about 74°F in winter to 85°F in the summer.
Wet and dry seasons 
Precipitation is characterized by dry and wet seasons. The dry season is from November through April, when the weather is normally sunny and dry. In some years the dry season can see very dry conditions, with little rainfall after mid December. May through October is normally the wet season, receiving approximately 63 percent of the yearly total in numerous showers and thunderstorms. Rain falls on most days of the wet season, though it falls in short and intense thunderstorms. Early morning is the favored time for these showers, which is different from mainland Florida, where showers and thunderstorms usually occur in the afternoon. Easterly (tropical) waves during this season occasionally bring excessive rainfall, while infrequent hurricanes may be accompanied by unusually heavy amounts. At any rate, Key West is the driest city in Florida.
|Climate data for Key West|
|Record high °F (°C)||90
|Average high °F (°C)||75.3
|Daily mean °F (°C)||70.3
|Average low °F (°C)||65.2
|Record low °F (°C)||41
|Rainfall inches (mm)||2.22
|Avg. rainy days (≥ 0.01 in)||6.5||5.6||5.0||4.7||7.6||11.0||11.7||14.5||15.6||10.4||6.5||6.5||105.6|
|Mean monthly sunshine hours||251.1||248.6||310.0||324.0||341.0||315.0||325.5||306.9||270.0||254.2||231.0||235.6||3,412.9|
|Source: NOAA (normals, 1971–2000) , HKO (sun, 1961–1990) , The Weather Channel (records) |
Hurricanes rarely hit Key West, and the island has been relatively lucky. Locals say that Hurricane Wilma on October 24, 2005, was the worst storm in memory. The entire island was told to evacuate. Business owners were forced to close their businesses. After the hurricane had passed, a storm surge sent eight feet of water inland, completely inundating a large portion of the lower Keys. Low-lying areas of Key West and the lower Keys, including major tourist destinations, were under as much as three feet of water. Sixty percent of the homes in Key West were flooded. The higher parts of Old Town, such as the Solares Hill and cemetery areas, did not flood, because of their higher elevations of 12 to 18 feet (5.5 m). The surge destroyed tens of thousands of cars throughout the lower Keys, and many houses were flooded with one to two feet of sea water. A local newspaper referred to Key West and the lower Keys as a "car graveyard." The peak of the storm surge occurred when the eye of Wilma had already passed over the Naples area, and the sustained winds during the surge were less than 40 mph (64 km/h). The storm destroyed the piers at the clothing-optional Atlantic Shores Motel and breached the shark tank at the Key West Aquarium, freeing its sharks. Damage postponed the island's famous Halloween Fantasy Fest until the following December. MTV's The Real World: Key West was filming during the hurricane and deals with the storm.
In September 2005, NOAA opened its National Weather Forecasting building on White Street. The building is designed to withstand a Category 5 hurricane and its storm surge. Tours of the office are available, weather permitting, Monday-Friday from 10am to 12pm.
The most intense previous hurricane was Hurricane Georges, a Category 2, in September 1998. The storm damaged many of the houseboats along Houseboat Row on South Roosevelt Boulevard near Cow Key channel on the east side of the island.
Attractions, events, recreation, and culture 
Many visitors rent a bicycle and explore the history and architecture of Old Town Key West. Walking tours, including a tour of the unusual Key West Cemetery, are available. The Sunset Celebration at Mallory Square is a daily spectacle for visitors and residents. Boat excursions and tours provide a great way to view Key West from the water.
The Duval Street bar and restaurant district includes many different entertainment options, all within walking distance of each other.
The Audubon House and Tropical Gardens is a museum dedicated to the art work of John James Audubon and history of Key West. This was founded by the Wolfson Family as they purchased the home of ship wrecking captain Geiger. John James Audubon painted many of the birds of Key West in this garden.
The Studios of Key West, founded in 2006 and based at the island's historic Armory building, was established as a new model for an artist community. It comprises a dozen working studio spaces, a main exhibition hall, a sculpture garden, and several adjoining residences and cottages. Its programming continues to grow and includes an extensive series of creative workshops, free humanities lectures, cultural partnerships, and innovative ideas for artists and audiences.
The Florida Keys Council of the Arts serves as the primary cultural umbrella for Monroe County, from Key Largo to Key West. A non-profit local arts agency, it makes grants, operates the Monroe County Art in Public Places program, sponsors seminars, and manages the on-line cultural calendar for the region. It also manages the County's Tourism Development Council arts marketing grants and serves as a leading advocate for cultural tourism in lower Florida.
Key West Contemporary Dance Company is a 501c3 nonprofit organization based out of Key West, Florida. Composed of local and visiting professional dancers, it performs at various venues throughout Key West and rehearse at The CoffeeMill Dance Studio in Old Town.
The Key West Literary Seminar, a celebration of writers and writing held each January, attracts an international audience to hear such writers as Ian McEwan, Margaret Atwood, Billy Collins, and Joyce Carol Oates.
Nancy Forrester's Secret Garden is a one-acre (4,000 m²) garden resembling a lush, predominantly green rainforest. It is an exhibit of nature's artistry in a woodland garden.
The Key West Butterfly and Nature Conservatory features a 5,000-square-foot (460 m²) glass-domed tropical butterfly habitat.
A permanent AIDS Memorial is at the White Street Pier.
The Mel Fisher Maritime Museum showcases gold, silver, and treasure recovered from shipwrecks around the world.
Some tourists mingle with the locals, shop, and dine at the Key West Historic Seaport at the Key West Bight.
The Key West Lighthouse and Keeper's Quarters Museum preserves the history of the Key West Lighthouse, built in 1847.
PrideFest is seven days of events, presented by the Gay and Lesbian Community Center of Key West during the first week in June. The schedule includes the Pride Follies talent extravaganza; contests to select a Mr., Ms. and Miss PrideFest; parties; a tea dance; and the PrideFest Parade down Duval Street.
In 1979 the Key West Tourist Development Association, Inc., started Fantasy Fest to attract tourists at the traditionally slow time of Halloween, which is at the end of the hurricane season. Fantasy Fest regularly attracts approximately 80,000 people to the island and has become a huge success.
In June 2006 the Key West Gay & Lesbian Museum & Archive opened at the Gay and Lesbian Community Center at 513 Truman Avenue. Featured exhibits include a Tennessee Williams typewriter as well as an extensive collection of memorabilia and papers of Richard A. Heyman, who was one of the nation's first openly gay mayors before dying in 1994 of AIDS.
Popular annual events 
- Key West Race Week – international sailing event – January
- Key West Literary Seminar – January
- Kelly McGillis Classic – Flag Football Tournament – February
- Conch Republic Independence Celebration – April 23
- Taste of Key West – April
- Red Ribbon Bed Race – April
- Key West Songwriters Festival – April / May
- Survivors Party – May
- Queen Mother Pageant – May
- PrideFest – June
- Cuban-American Heritage Festival – June
- Hemingway Days Festival – July
- Key West Lobsterfest - August
- WomenFest – September
- Bike Week – September
- Fantasy Fest – October
- Goombay Celebration – October
- Robert the Enchanted Doll Day – October 24
- Parrot Heads in Paradise Convention (aka Meeting of the Minds) – Nov 2–6 (2011)
- Boat and Holiday Parade – December
The television stations received in Key West are the stations in the Miami-Fort Lauderdale Designated Market Area (DMA) (defined by Nielsen Media Research) with rebroadcast transmitters in Key West and Marathon, Florida. Comcast provides cable television service. DirecTV and Dish Network provide Miami-Fort Lauderdale local stations and national channels.
The Key West area has 11 FM radio stations, 4 FM translators, and 2 AM stations.
The Florida Keys Keynoter and the Key West Citizen are published locally and serve Key West and Monroe County. The Southernmost Flyer, a weekly publication printed in conjunction with the Citizen, is produced by the Public Affairs Department of Naval Air Station Key West and serves the local military community.
Key West has five public schools including Key West High School, Home of the Conchs, the only high school on the island. There is one public Middle School, Horace O'Bryant and three elementary schools, Glynn Archer Elementary, Poinciana Elementary and Montessori Charter School.
Florida Keys Community College operates its main campus in Key West.
Notable Key West persons 
Notable Key West natives 
- Bronson Arroyo, baseball player
- Stepin Fetchit, comedian
- Amber McDonald, actress
- George Mira, football player
- David Robinson, basketball player
- David Wolkowsky, real estate developer and preservationist
Notable Key West visitors 
- John James Audubon
- Elizabeth Bishop, poet
- Judy Blume, children's author
- Jimmy Buffett, musician
- Tom Corcoran, author
- Mel Fisher, treasure hunter
- Ernest Hemingway, author
- Calvin Klein, fashion designer
- Mike Leach, American football coach
- Alison Lurie, novelist
- Stephen Mallory, politician
- Kelly McGillis, actress
- James Merrill, poet
- John Dos Passos, novelist
- Boog Powell, baseball player
- Thomas Sanchez, author
- Shel Silverstein, author
- Wallace Stevens - poet
- Keith Strickland, musician, songwriter and founding member of The B-52s
- Michel Tremblay, Canadian playwright
- President Harry S. Truman, U.S. president
- Tennessee Williams, author
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- Boog Powell - Key West High School graduate
- Boog Powell - Key West High School graduate
- Key West - Famous natives and residents
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- Official City Website
- Chamber of Commerce Website
- Monroe County School District—Key West Public Schools
- A photographic tour of Key West
- Key West Art Galleries
- Sanborn Insurance Historical Maps of Key West
- Key West nightlife (photos)
- Key West Citizen
- Nautical Chart of Key West
- Bus Service from Miami to Key West XcursionsUSA.com