The Architecture and Culture of Old Town, Key West

With its characteristic pastel-hued cottages, towering palm trees, and breezy tropical vibe, Key West’s Old Town transports visitors back to a bygone era. The historic district charms with its laidback atmosphere and eclectic blend of architectural influences that reflect the island’s complex history and culture.

Early Development

Modern-day Key West began as a sparsely populated island used occasionally by fishermen and pirates as a rest stop. In 1815, Florida was ceded to the United States from Spain, and Key West’s potential as a naval base was recognized. By the 1820s, the U.S. Navy had set up a large operation on the island, brings growth and prosperity.

As Key West established itself as a fishing village in the early 1800s, Bahamian ships began frequenting its port. Africans liberated from these ships built the first settlements, bringing the Bahamian style of architecture now seen throughout Old Town. Hallmarks include raised cottages with long porches, slatted shutters, and steep metal roofs.

This Bahamian influence merged with building styles later brought by settlers from Cuba and other Caribbean islands. The peak era of development in Old Town was between 1880 and 1912, when thriving maritime trades attracted diverse new residents. Cuban émigrés in particular left their mark in the late 1800s after Cuba’s war for independence. They imported the Spanish Colonial architecture of their homeland, as evidenced by many of the larger mansions.

Distinctive Building Types

Shotgun Houses

One of the most iconic structures of Old Town are shotgun houses, named because shots fired through the front door would fly clean through to the back door. These narrow single-story homes originated in the Caribbean and West Africa. They reflected the housing needs of the working class free black settlers and Bahamian spongers who flocked to Key West in the 1800s.

Shotgun houses are tightly packed together in rows and feature a long rectangular floor plan. They have plain exteriors, double-hung windows, front porches, and distinctive rooflines that slope down toward the back. The ones in Key West often have decorative trim in gingerbread shapes or with fish scale-like shingles.

Conch Houses

Many of the larger homes in Old Town are built in the Conch style, named after the term used to refer to native Key Westers. Adapted from traditional Bahamian dwellings, these houses incorporate elements of both Caribbean and American Victorian architecture. They have wrap-around verandas ideal for capturing the breeze, pillars, tall windows, and ornate trim.

Conch houses range from one to two stories high and were typically painted white to reflect heat. Their ceilings are built unusually tall to accommodate hot air rising. Some contain nicer furnishings as many belonged to wealthy wrecking captains and successful merchants. Prominent examples include the Audubon House and Porter House.

Cigar Factories

Beginning in the 1860s, many Cuban cigar factories popped up in Key West, bringing an influx of skilled Cuban workers. Some of the larger factory buildings are still standing, like the three-story Sanchez & Haya factory on Simonton Street. Built in 1866, it is now an apartment building recognizable by its long rectangular shape and rows of tall arched windows.

Other factories have been converted into restaurants, art galleries, and museums, like the Half Shell Raw Bar and Cuban Coffee Queen. These iconic structures represent the island’s hand-rolled cigar tradition, which earned it the nickname “Cigar City.”

Classic Floridian Architecture

While Bahamian and Caribbean influences dominate, Old Town also features some classic Floridian architectural elements. Porch-wrapped wood cottages, reminiscent of Northeastern beach homes, reflect the New England heritage of some settlers. Many Victorian era mansions and Queen Anne cottages display ornate spindlework, turrets, and gables.

Florida’s frontier building style is apparent in structures like clapboard houses, tin-roofed warehouses, and Victorian “islander cottages” with wraparound verandas. This diversity of architectural forms gives the streets of Old Town a textured, patchwork feel that invites wandering and discovery.

Writers and Artists of Key West

In the early 20th century, Key West began attracting writers, artists and eccentrics drawn to its tropical remoteness. The most famous was Ernest Hemingway, who lived in Key West throughout the 1930s in a Spanish Colonial mansion where he penned classics including For Whom the Bell Tolls.

Other literary figures like Tennessee Williams, Robert Frost, and Elizabeth Bishop were also inspired by Key West, forming an informal artists’ colony. Their presence fostered an appreciation for the history and architecture of Old Town, helping preserve its heritage. Many of their former homes are now popular attractions, like the Ernest Hemingway House & Museum.

Key West Life and Traditions

Beyond the architecture, Old Town’s culture is rich with unique local traditions that shape everyday life. Locals embrace an island pace and ethos known as “Key West time.” Siestas are common to escape the midday heat. Many make their living from the sea as fishermen, shipwrights, treasure salvagers, and spongers.

The “Conch Republic” flag representing Key West’s irreverent spirit flies over Old Town. Streets have colloquial names like Petronia, Angela and Olivia honoring ancestors. Homes often display ‘Conch-style’ fences made from conch shells limestone or coral rock. Roosters and chickens, descendants of Cuban fighting cocks, roam freely.

Corner bars, Southern home cooking at diners, and live music pouring from nightclubs create a lingering old Florida ambiance. The sunset celebration in Mallory Square carries on a tradition of welcoming incoming ships to port. Key lime pie and rum cake are iconic local foods, along with Cuban dishes like picadillo, papaya, and Cuban coffee.

While today dominated by tourism, Old Town still maintains its heritage as a haven for free-spirits seeking inspiration. The architecture both shapes and reflects the island’s cross-cultural history and enduring maritime spirit. From its sunset views to beachside cottages, Old Town evokes nostalgia for the Florida Keys’ past. It remains a tropical time capsule promising wanderlust and escape.

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