A — hops off the plane or the cruise ship in Key West and heads right to the Green Parrot or the Chart Room, eager to begin your vacation drunxtravaganza. But have you ever looked around while you were crawling from one bar to the next and caught a glimpse of a building (even through squinty, blurry eyes) and wondered where it came from? What its purpose was? What mysteries hide behind the bricked façades and stuccoed patinas? Indulge us while we take you for a walk back in time, when Key West was a haven for pirates, fishermen and artists alike; when there were no $5 T-shirt shops and neon lights to distract from the architectural wonders that polka-dotted the island; and when Key West was much more than just bar crawls and beach days.
We’ll start today’s tour at the Custom House Museum, at 281 Front St. The monstrous red brick building was, as you might have guessed, originally built to serve as the U.S. Custom House, but customs operations only formed a small part of what transpired inside its walls. Key West became a U.S. territory in 1821 and in January of 1822, shrewd Alabama businessman John Simonton, knowing the island sat smack in the middle of lucrative trade routes, purchased it for $2,000. That proximity to trade routes connecting major ports in the U.S., the Caribbean and the Americas made Key West an ideal destination for both entrepreneurs and the U.S. military, which in turn led to a major industrial influx, including everything from salvaging, fishing and sponging to sea salt harvesting and cigar manufacturing. These industries formed the backbone of Key West’s 19th century economy and by 1890, Key West was the largest city in Florida with a population of 18,000.
Recognizing the importance of Key West’s growing sea-based economy, the U.S. Treasury authorized construction of the Custom House in 1885 to accommodate its customs operations. The building’s Richardsonian (no relation, sadly) Romanesque architecture was all the rage on the mainland at the turn of the 19th century. The original structure housed the customs offices, district court and post office. But the Great Depression hit the island hard and in July of 1934, Key West, once one of the richest cities in Florida, formally declared itself bankrupt. Once-beautiful Conch homes went unpainted and unrepaired, the beaches teemed with weeds, debris littered the narrow streets and dilapidated, uninhabited storefronts became commonplace. Customs diminished and the court and post office moved to other locations. The Navy took possession of the building for the next decade but eventually abandoned it when military need for it subsided. The building stood vacant for the next 20 years and in 1993, the Key West Art & Historical Society undertook an extensive $9 million restoration of the dilapidated structure, returning it to its original splendor. Today, the awe-inspiring edifice houses the Custom House Museum, whose leadership (quite intentionally) dedicates itself to filling the walls with exhibits that celebrate the colorful history of Key West — a mission befitting the historical importance of the building in which they reside.
A short walk away, at 319 Duval St., sits the Key West Woman’s Club. This red brick home was built by Capt. Martin Hellings in 1892. Capt. Hellings was the manager of the International Ocean Telegraph Company, a job with undeniable importance when you consider that, before the advent of radio and telephones, the telegraph was the only way to communicate long distances. In 1940 the building was purchased by the Key West Woman’s Club, which converted the left half of the building into the only public library in Monroe County (the library is now at 700 Fleming St.). Behind the house, the red frame structure with a gabled metal roof now houses the Red Barn Theatre. To this day, the building remains one of the few privately owned mansions on Duval Street. Tours of the Hellings House Museum are offered on Tuesday, Wednesday, Thursday and Saturday.
Around the corner, at 410 Caroline St., sits the Capt. George Carey House, likely the second oldest structure in Key West. This house was built in 1834 by Capt. George Carey, a wealthy Englishman who — surprise, surprise — ran a seaport bar and wholesale liquor business. The original house was quite small, consisting of two rooms and a separate cookhouse at the rear of the property. In 1844, Capt. Carey enlarged it to its current size for his bride, a German woman who, along with her four sisters, was rescued from a shipwreck off the coast of the island. The women all married men from Key West, and the shipwreck came to be known as the “Wreck of the German Brides.”
The house changed hands a number of times over the years. In 1934 it was purchased and restored by Jesse Porter, a fifth-generation Key Wester. Miss Jesse, as she was known to her friends, was instrumental in saving many historic Key West structures and in creating the island’s Old Town historic district. She lived in the house from 1934 until her death in 1979. During her life, her home became the gathering place for many of Key West’s famous visitors and residents, including Gloria Swanson, Tennessee Williams, Truman Capote, Ernest and Pauline Hemingway, John Dos Passos and Wallace Stevens.
The small single-story cottage to the right of the house opening onto the backyard is named for the poet Robert Frost, who spent 16 winters there as a guest of Miss Jesse starting in 1945.
The Pirates Well, allegedly the first source of fresh water in Key West, sits to the left of the house.
Head down the block and make a right on Simonton to hit Casa Antigua, at 314 Simonton St. In 1919, Benjamin Trevor and George Morris built Casa Antigua, which was then known as the Trev-Mor Hotel, one of Key West’s first hotels. After the devastating fire of 1886, the Trev- Mor was advertised as the island’s first fireproof hotel because it had 13-inch-thick walls made from bricks recycled from Fort Zachary Taylor.
The hotel offered 46 rooms on the second and third floors; the first floor contained a Ford car dealership.
In April 1928, Ernest Hemingway and his second wife, Pauline, arrived in Key West on an oceanliner, fresh off a seven- year residency in Paris. Hemingway intended to pick up a Ford Roadster from the Ford agency so the couple could drive up the Keys to the mainland. But the car delivery was late and the Hemingways were stranded for two weeks (there are worse places to be stranded, am I right?).
Mr. Trevor and Mr. Morris apologetically put the couple up in a room on the second floor.
During this unplanned stay, Hemingway fell in love with Key West. He could see the seaport from the hotel, and the deep-sea fishing boats moored at Mallory Square were a short stroll away (as were Sloppy Joe’s and Captain Tony’s bars). Hemingway was apparently so inspired by Key West that he stayed at the hotel for two years and finished “A Farewell to Arms” there before moving into the now-famous house at 907 Whitehead St.
As the years went by, the fortune of the Trev-Mor Hotel tanked. In the 1950s, the first-floor car dealership was transformed into a jazz club. In 1975, having survived 56 years of brutal hurricanes, the “fireproof” building was ironically gutted by fire. In 1978, the building was converted to a private residence and renamed Casa Antigua (“old house” in Spanish).
The remains of the historic hotel hotspot have been transformed into one of the most unusual homes on the island. Its three-story, open-air interior atrium that overflows with tropical plants surrounding a pool that was once the property’s cistern.
Returning to Duval Street, it’s hard to pass by The San Carlos Institute, at 516 Duval St. The Cuban heritage center was founded in 1871 by Cuban exiles who came to Key West to plan the campaign for Cuba’s independence from Spain. José Dolores Poyo and Juan María Reyes, two distinguished leaders of Key West’s robust Cuban community, proposed the establishment of an organization dedicated to promoting Cuban cultural values and patriotic ideals. The San Carlos was principally supported by the contributions of the Cuban tobacco workers of Key West, who donated a substantial portion of their modest wages to the formation of the Institute.
The institute was inaugurated on Nov. 11, 1871, in a small wooden building on Anne Street and named after Cuba’s Seminario San Carlos, a place of higher learning renowned for academic excellence. Classes were taught in English and Spanish to children of all races, and the San Carlos became one of the nation’s first bilingual integrated schools.
The San Carlos moved to larger quarters on Fleming Street in 1884. Two years later, the building burned to the ground in the fire that destroyed much of Key West.
In 1890, the San Carlos was rebuilt at its present location on a spacious lot fronting Duval Street in the heart of Key West’s historic district. Many legendary figures of Cuba’s independence movement addressed the exiled Cuban community at the San Carlos Institute, among them José Martí, Cuba’s legendary patriot and poet, who loved the San Carlos so much that he called it “La Casa Cuba.” When the Cubans waged their War of Independence and rid Cuba of Spanish colonial rule in 1902, jubilant exiles gathered at the San Carlos to celebrate. And when the San Carlos was damaged beyond repair by a hurricane in 1919, Key West’s Cuban community sprang into action to restore it to its former glory, securing $80,000 from the Republic of Cuba for the reconstruction.
Francisco Centurión, one of Cuba’s most prominent architects, designed the present two-story building, incorporating many elements of classic Cuban architecture: spacious rooms, high ceilings, graceful curves and arches, marble stairways, louvered windows, handcrafted mosaics and floors of checkered Cuban tile.
The magnificently restored building opened on Oct. 10, 1924, and was referred to by many as “the jewel of Key West.” The school ceased operation in 1973, after communist dictatorship seized power in Cuba in 1959, which caused the financial assistance provided by the Cuban government to cease.
The building remained closed for almost two decades, during which time many of the San Carlos’ books and records were lost to the elements or to vagrants who sought shelter in the vacant building. When a portion of the facade collapsed in 1981, injuring a passing tourist, some called for the building’s demolition. Other sought to restore it as a commercial theater.
In 1985, in a desperate effort to save the San Carlos as a Cuban historical landmark, the Cuban residents of Key West and Miami appealed to the Florida Hispanic Commission for relief. Eventually, they were able to convince the commission of the building’s historic importance and raise the funds for a complete renovation. Community leaders, architects, builders and artisans donated their skills to the effort, and a beautifully restored San Carlos Institute opened on Jan. 4, 1992, exactly 100 years from the day José Martí delivered his first address at the institute. Today, the San Carlos Institute serves as a historical archive, classroom, gallery, community gathering place and public theater.
We’ll end our historic architecture tour at arguably the most colorful edifice in Old Town, the Southernmost House Hotel. This impressive Queen Anne Victorian house was designed as a one-bedroom mansion and built by Judge Vinning Harris in 1897. What it lacked in bedrooms it more than made up for with its expansive views, elegant public rooms, two-story balconies and large stained glass windows.
During the Prohibition period from 1919-1933, the mansion’s first floor was a restaurant, the second floor was used for gambling and the third floor for “socializing.” Naturally, it became an attractive stopping point for celebrities and gangsters en route to Havana.
In the 1940s, the mansion operated as a night club called Café Cayo Hueso, hosting the usual Key West suspects, including Ernest Hemingway, Tennessee Williams, Gore Vidal, Truman Capote, Tallulah Bankhead, Gloria Swanson, Louis Armstrong and Charles Lindbergh.
In 1949, it was completely renovated for use as a private residence. Since then, many dignitaries have been welcomed there, including American Presidents Harry Truman, Dwight Eisenhower, John Kennedy, Richard Nixon and Jimmy Carter.
Now that you’ve filled your brain with all of this archaic architectural information, it’s probably time to obliterate some brain cells. Go ahead — historical exploration is thirsty work and you’ve earned every sip. ¦