Key West History and Culture Bike Tour

Entries on This Tour

1. West Martello Tower (Key West Garden Club)

Though Florida joined the Confederate States, Key West remained a Union stronghold. Fort Taylor's construction finished just as Lincoln was taking office, but as war commenced, federal and local officials agreed that more protection was needed along the beaches to supplement the fortification. However, yellow fever outbreaks, storms, and supply issues prevented the full plans for the West Martello Tower to be realized; only the masonry work was completed. Construction ceased after the war, although modifications occurred during the Spanish-American War. It stands as a reminder of the need to protect Key West from landing forces, even through World War II. Today, it serves as the home to the Key West Garden Club.

2. African Cemetery at Higgs Beach

The African Cemetery at Higgs Beach is located in Key West and has the graves of Africans who died after being rescued from slavery. At Higgs Beach, next to the West Martello Fort and near White Street Pier, people are able to glimpse into history and discover more about one of the first events to occur in Key West that presents compassion and acceptance.

3. Eduardo H. Gato House

The historic house was built in 1894 for the highly successful cigar industry tycoon, Eduardo H. Gato. As a Cuban patriot that helped support a failed Cuban Revolution during the 1860s and 1870s, he fled with many Cubans to Key West. Gato subsequently developed a booming cigar-making operation that sold cigars to people all over the world. In addition to his personal success, his industry helped Key West evolved into Florida's largest and wealthiest city during the 1890s. The home emerged at the peak of his success, although he returned to Cuba a few years after its completion, around the time of the Spanish-American War. While he was away, his home became the Mercedes Hospital, named after Gato's wife. The hospital served Key West until World War II. By 1917, Gato had expanded his Key West business, constructing the first fireproof cigar factory.

4. Peary Court Cemetery

The Peary Court Cemetery, located within the Key West, Florida’s Historic District, comprises approximately one acre of land. Associated with the U.S. Army, records indicate the first interment was in July of 1835. In 1998 the cemetery was transferred to the City of Key West through the Historic Surplus Property Program. Today the property is maintained as an historic open space and cemetery.

5. The Armory in Key West

Constructed in 1901, this historic armory served as the headquarters of a Key West militia unit that was established decades prior during the Civil War to protect against Confederate forces. The Florida Keys were of strategic importance to intercepting Southern shipping, and Key West remained a strategic naval location after the war. The Armory served local and national forces through World War II, part of a longstanding relationship between the island city and the U.S. military that dates back to the first presence of Americans in Key West in the 1820s. Since the Second World War, the building has mainly functioned as a community center followed by a home to local artists.

6. 500 Simonton Street (Key West Drug Company Building)

One of the oldest brick structures in Key West, this building was home to the Key West Drug Store for decades starting in 1903. The Building was part of the Maloney family's vast real estate holdings on the island. Colonel Walter C. Maloney arrived in Key West just as the U.S. took possession of the island in the 1820s. Maloney and his descendants acquired land, built buildings, and also published books, established hospitals, held political office, and developed radio stations. John Maloney, the third generation of Maloneys in Key West, established the Key West Drug Store here in 1903. A practicing surgeon, John Maloney developed a hospital that connected to the pharmacy after an explosion injured numerous workers developing the Florida East Coast Railroad. The railway, which connected the southern Florida mainland to Key West comprised a series of steps during the twentieth century to boost Key West's tourism and real estate industries. Maloney also took the lead in creating the island's hospital, which included space to perform surgery. The pharmacy fell into the hands of Maloney's daughter Florence who lived in the building until the 1980s. Her kids and grandkids went on to develop businesses, serve in public offices, and eventually renovate the former drug store. The first floor is home to retail while the second floor of the historic building offers rooms for rent to island visitors.

7. San Carlos Institute and Theatre

Cuban exiles established the San Carlos Institute in 1871 and built this theater in 1890. This theater was the location where noted revolutionary José Martí united the Cuban exile community and launched the final phase of his campaign to achieve Cuban independence from Spain in 1892. The Institute was formed as a place for Cubans in Key West to maintain their cultural identity, which included hosting touring theatre companies, musical performances, and the ballet. Today, the theater continues to host shows while the Institute as a whole serves as a museum, library, art gallery, theater, and school.

8. La Concha Hotel & Spa

Key West's La Concha Hotel & Spa was completed in 1926, an era of growth and great optimism for the island city as investors pinned their hopes on the booming real estate in southern Florida and construction of a railroad and road that would connect Key West to the Florida mainland. At six stories, the hotel towered above Key West and it proved to be the island's first, true luxury hotel. Early success did not arrive though, as the island's economy suffered during the late 1920s and became even more challenging during the Great Depression. However, federal support in the form of New Deal investment aided Key West's tourism industry and the hotel. The hotel benefited from the investment in infrastructure and grew into one of the most iconic hotels in Key West. The hotel has hosted a variety of visitors and was also a favorite of Key West residents such as Ernest Hemingway and Tennessee Williams. The hotel currently operates as Crowne Plaza Key West-La Concha.

9. Oldest House Key West Museum

Built between 1825 and 1829, this is the oldest surviving house in southern Florida and also home to a local history museum. For decades, this was the home for Captain Francis and Emeline Watlington and their seven children. Francis arrived in Key West from New York in 1840 to work as a wrecker, a flourishing enterprise that involved ships racing to meet other ships that ran aground. As a reward or settlement, the wreckers gained possession of a percentage of the cargo, which they sold for profit. In addition to artifacts from the Watlington family and other Key West items, the museum also offers items related to the storied history of the shipwrecking industry.

10. Key West Woman's Club (Hellings House)

Successful merchant, and Florida's first millionaire, William Curry, provided his children with money to build and develop property. His daughter, Eleanor, and son-in-law, Captain Martin Hellings, used that money to build the Victorian Mansion in 1892. Captain Hellings managed the International Ocean Telegraph Company, a prominent position in the 1890s. His expertise with handling tele-communications allowed him to steal messages from Spain during the Spanish-American War, which helped the U.S. Navy and White House during the war. The current occupants, The Key West Woman's Club, purchased the building in 1940.

11. Dr. Joseph Y. Porter House

This historic antebellum mansion stands on land that was purchased in 1837 by Judge James Webb, the first Federal Judge of the Southern District of the Florida Territory, and the builder of the historic home sometime over the next eight years. Dr. Josephy Porter's father purchased the property in 1845 and Joseph was born in the house two years later. Dr. Porter went on to become Key West's first native-born physician and he served as Florida's first Public Health Officer from 1889–1917. Porter is most known for his research and treatment of yellow fever The Key West physician discovered that mosquitoes carried the deadly virus from one host to another. Demonstrating the origins of the disease helped other researchers, and eventually led to the eradication of the deadly Yellow Fever.

12. Casa Antigua (Trev-Mor Hotel)

The Trev-Mor Hotel, now known as Casa Antigua, opened in 1919 and eventually became the place where Ernest Hemingway stayed and fell in love with Key West. Hemingway, with his new bride Pauline, intended to pick up a new Ford from the Trev-Mor Ford Agency located on the first floor of the hotel, but its arrival was delayed by two weeks. The building owners, embarrassed, provided lodging to the new couple and the famed author's love affair with the island was born. Their intention to pick up the car and drive to Miami on the new highway never materialized. Instead, the couple stayed on the island for a decade. In the late twentieth century, the hotel transitioned into a private residence and renamed Casa Antigua.

13. Western Union Schooner

Launched in 1939, the Western Union is the last surviving and working tall wooden ship to be constructed in Florida. From 1939 to 1974, the Western Union Telegraph Company. used the ship to lay more than 30,000 undersea wires, maintain cables connecting numerous Caribbean cities, and lay the first trans-Atlantic telephone wire. In 1997, the ship was featured in Steven Spielberg's Amistad. As of the spring of 2021, the historic ship is undergoing repair and expected to return to this location in Key West's port in the summer of 2021.

14. Old City Hall

Although it is no longer used for its original purpose, the Old City Hall building remains an important landmark in Key West. It was constructed in 1892 and served as the seat of city government until 1965. Today it houses the Key West Chamber of Commerce and a visitors center, and is managed by the Historic Florida Keys Foundation. The brick building features a bell and clock tower, arched windows, and a large granite staircase. The second floor room has two-hundred seats and is available to the public for group meetings and presentations.

15. Audubon House Museum

The Audubon House and Gardens were established by a key west native names Colonel Mitchell Wolfson and his wife Frances. It was a house originally built by Key West's first harbor captain, John Huling Geiger. He planted beautiful vegetation outside of the house which caught the Colonel's eye. Its original style was the American Classic Revival.

16. Mel Fisher Maritime Museum

Founded in 1985, the Mel Fisher Maritime Museum is dedicated to preserving and promoting the rich maritime history of Florida and the Caribbean. It is named after treasure hunter Mel Fisher (1922-1998), who is known for discovering the Spanish galleon the "Nuestra Señora de Atocha" in the early 1970s. The cargo was estimated to be worth around $400 million. In addition to the Atocha, Fisher also found the slave ship, the "Henrietta Marie." Its artifacts comprise the most complete collection of items from a slaving ship in North America. The museum features several exhibits that explore several topics including the life and legacy of Mel Fisher, the search for the Atocha, the science of shipwrecks, piracy, the transatlantic slave trade, and artifact conservation. The museum is housed in the history Key West Naval Storehouse, which was built in 1910. The museum offers a variety of educational programs and conducts underwater excavations of shipwrecks.

17. Naval Depot and Storehouse and U.S. Coast Guard Headquarters

The former Naval Depot and Storehouse and U.S. Coast Guard Headquarters building was erected between 1856 and 1861, making it the oldest brick building on Key West. It was also the first permanent Naval building on the island. Today it is called the Clinton Square Market and is home to a variety of retail shops. In terms of design, it features buttressed piers, arched window recesses, and large arched entrances at either end. The building was listed on the National Register of Historic Places in 1973.

18. William Wall Warehouse

William Wall set sail for Key West in 1824 and, like countless others near the island during the 1820s, wrecked his ship. While many Key Western residents profited greatly from obtaining goods from wrecked ships, Wall turned his misfortune into an actual fortune. He decided to stay on the island and, in 1831, created the island's first cigar factory. Not only did he amass a fortune, he set in motion an industry that supported more than 130 cigar factories by 1900. Wall's descendants built the warehouse in 1878 just as Cuban exiles arrived in Key West by the thousands. A few years later, the U.S. Navy purchased the warehouse mostly because if its coal supplies and storage vessels. One of the Navy ships that docked near the warehouse was the infamous U.S.S. Maine that exploded outside of Havana, leading to an outcry, justified or not, that helped push the the U.S. and Spain into war.

19. Old Post Office and Customshouse (Key West Museum of Art & History)

The historic Key West structure was completed in 1891 and served as the home to the U.S. Customs, U.S. Post Office, Superior Court of the Southern Judicial District, and The Lighthouse Department. The building was constructed at a moment in time when Key West was South Florida's wealthiest and largest city owing to federal investment owing to its status as an official U.S. Port Entry. An examination of parts of the U.S.S. Maine, a battleship that exploded and sank in the Havana harbor, occurred at the Customshouse. The event led to speculation that Spain was behind the attack, and despite an inconclusive analysis, those who hoped the incident would lead the U.S. to challenge Spain's control of Cuba and other islands used the explosion to rally support for the Spanish-American War. The building later served as offices of the U.S. Navy until the 1970s. Demonstrating the island's transition to tourism, the building is now home to the Key West Museum of Art & History. That organization led a restoration project of the building during the 1990s and have been operating in the historic structure since 1999.

20. Harry S. Truman Little White House

This historic building served as the Key West naval station's command headquarters during the Spanish-American War, World War I, and World War II. President Harry Truman later used the facility and gave it the nickname "Winter White House." The historic home has been used by a total of six American Presidents, but Truman's lengthy visits led to its association with him and the nickname "Truman's Little White House." Today the building holds a small museum that introduces guests to the history of the site and its role in naval history, as well as its place in history during the Truman Presidency and the Cold War.

21. United States Weather Bureau (Weatherstation Inn)

Now a hotel called the Weatherstation Inn, this historic building was once a station of the United States Weather Bureau, which was the predecessor to the National Weather Service. Designed by architect Frank H. Jackson in the Classical Revival style, the building was erected in 1912 and was occupied by the Bureau until the 1950s when the Navy acquired the structure. This facility was part of a network of weather stations around the country and played a critical role in reporting weather to the public and predicting the path of hurricanes and storms. The inn opened in 1977.

22. USCGC Ingham Maritime Museum

Now a museum ship, the Ingham is a historic Coast Guard cutter vessel that operated from 1936 to 1988. It is one of only two (of seven) Secretary-class cutters remaining and was the most-decorated Coast Guard vessel. The Ingham is also the only cutter to receive two Presidential Unit Citations during World War II. During World War II, it escorted convoys to Britain. On one trip in December 1942, the Ingham sunk a German U-Boat 626 on the 15th with a single depth charge. Known as the "hole in one," the sinking of the U-262 was the last U-boat sunk by an American ship in the war. The Ingham was named after Treasury Secretary Samuel D. Ingham, who served under President Andrew Jackson (the six other cutters were named after other Treasury Secretaries). It is a National Historic Landmark and listed on the National Register of Historic Places.

23. Ernest Hemingway House

This museum and historic site was home to Ernest Hemingway from 1931 to 1939, although he retained title to the home until he died. The house was one of the first on the island to be fitted with indoor plumbing, and also featured the first swimming pool in Key West. More importantly, this is the house where Hemingway wrote some of his most important works such "The Snows of Kilimanjaro," "The Short Happy Life of Francis Macomber," "To Have And Have Not," and "Green Hills of Africa. The museum provides guided tours of the home and the grounds every fifteen minutes between nine to five.

24. Key West Lighthouse and Museum

Following the devastating hurricane of 1846, this historic lighthouse was completed in 1848 and replaced Key West's first lighthouse which had been built in 1825 and had been destroyed in the storm. Michael Mabrity served as the first lighthouse keeper from 1825 until he died in 1832. At that time, Barbara Mabrity took over and held the keeper position for thirty years. In addition to losing her husband, Barbara also lost six children who, along with eight other people, took refuge in the tower during that devastating hurricane. During the 1860s, Barbara made anti-Union statements despite the fact that Key West remained part of the Union during the Civil War and was a key part of the Union's naval strategy. These pro-Confederate remarks resulted in Marbity being removed from her post as the navy favored a lighthouse keeper who was loyal to the United States. The original lighthouse was fifty feet high with a base that was fifteen feet above sea level. However, the Key West building boom and growth during the late nineteenth century forced the island to raise the ground so the tower lights sat 100 feet above sea level. In 1969, the Coast Guard decommissioned the tower. By the late 1980s, the tower underwent renovations that ultimately resulted in its current function as a museum. In addition to exhibits, viewers can also climb to the top of the Key West Lighthouse.

25. Old Navy Commissary (Gato Cigar Factory)

Key West, Florida’s cigar manufacturing industry was beginning to come to prominence in the mid-1870s and The Gato Building played a central role. One of only three standing Key West cigar factories, the building was transferred to Monroe County in 1998 through the Historic Surplus Property Program. Today the building provides offices and a small exhibit space.

26. The Southernmost Point Buoy of Key West

The Southernmost Point Buoy of Key West was built out of necessity in 1983 to replace a series of signs that were stolen by tourists. The buoy is not an official point of navigation, but for many, it represents the southernmost point in the continental United States. For others, this point serves as a reminder of the many would-be Americans who have died in their efforts to come to America. The buoy notes that Cuba is only 90 miles away from that point and while it has become a tourist attraction, it is also a reminder that this point of entry to the United States has been reached by many after an arduous journey.

27. Southernmost House

Numerous celebrities and dignitaries have visited this Key West mansion which was completed in 1897, including five U.S. Presidents, Louis Armstrong, Charles Lindbergh, Ernest Hemingway, and Gloria Swanson. Thomas Edison oversaw the electrical design of the building, a rare feature for any home during the 1890s. The Queen Anne Victorian home was built by Judge Vinning and Florida Harris. Florida's father was the state's first millionaire. Over the years the home has operated as a private residence, speakeasy, nightclub, and a bed & breakfast.

This Tour is a Driving or Biking Tour.

Key West History and Culture Bike Tour

Created by Clio Admin on March 9th 2021, 2:30:33 pm.

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Description

Starting at Higgs Beach, this tour winds through the western portion of Key West with stops at over twenty landmarks, museums, monuments, and historic homes. Highlights of the tour include famous landmarks like Truman's Little White House and the Ernest Hemingway House, but the tour also includes stops at places that were central to world events such as the Spanish-American War. This tour is a work in progress; more entries will be added soon.

Entries on This Tour

Key West History and Culture Bike Tour

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