Key West Historic District Walking Tour

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic buildings with unique histories, uncovering tales of colorful figures who shaped the island, from renowned writers to influential locals.
As we stroll through beautifully preserved architecture, you’ll gain insights into the significance of each site, connecting with the spirit of Key West. This tour offers a chance to experience the essence of the island through its rich stories, creating an unforgettable adventure filled with intrigue and nostalgia. Don’t miss out on this magical journey!

Meeting Point

518 Duval St

518 Duval St, Key West, FL 33040, USA

San Carlos Institute, 516 Duval Street, Key West, FL, USA

What's included:

• Local Tour Guide

What to expect:

Duration: 1 hour, 30 minutes

San Carlos Institute

516 Duval St, , Key West, 33040-6553, Florida

The San Carlos Institute in Key West, Florida, is a historic cultural and educational facility established in 1871. It serves as a museum, library, art gallery, theater, and school, primarily focused on preserving and promoting Cuban heritage and culture. The institute played a significant role in Cuba's independence movement, as it was here that José Martí united the Cuban exile community in 1892 to launch his campaign for independence.
The San Carlos is not only a center for cultural events but also hosts various art exhibitions, performances, and educational programs, making it a vibrant hub for the community. Its architectural style reflects the late 19th-century influences, and it continues to be a symbol of the strong ties between Key West and Cuba. The institute remains a vital part of the local landscape, celebrating the rich history and contributions of Cuban immigrants in the area.

10 minutes

Duval Street

Key West, 33040, Florida

We will walk thru the hear of Key West party central, the famous Duval Street

Pass by without stopping

Capt Tony’s Saloon

428 Greene St, Key West, FL 33040, USA

The building at 428 Greene Street has a vibrant history reflective of Key West itself. Originally constructed in 1851 as an ice house and morgue, it later served as a wireless telegraph station during the Spanish-American War and hosted a cigar factory and bordello. After a brief stint as the Duval Club, known for its lavish parties that drew Navy scrutiny, it became a series of speakeasies, the last being The Blind Pig, which thrived on gambling and bootleg rum.
In 1933, Joe 'Josie' Russell transformed the space into Sloppy Joe’s Bar, named after a friend of Ernest Hemingway. The bar became Hemingway's favorite haunt until 1938, when Russell and his patrons moved it to 201 Duval Street. After several changes, the bar was purchased in 1958 by Captain Tony Tarracino, who renamed it Captain Tony’s Saloon. It became a launching pad for Jimmy Buffett in the early '70s, who often played there and celebrated the bar in his song "Last Mango in Paris."

10 minutes

The Studios of Key West

533 Eaton Street, , Key West, 33040-6801, Florida

The Studios was established to connect world-class artists with local audiences and foster creativity. We’ve welcomed Pulitzer Prize winners and renowned musicians, introducing thousands of students to diverse artistic perspectives. Our Helmerich Theater showcases exceptional talent, rooftop concerts fill the neighborhood with music, and each month, hundreds visit The Studios for new experiences and to reconnect with friends.

10 minutes

Curry Mansion Inn

511 Caroline St, , Key West, 33040-6604, Florida

William Curry, recognized as Florida's first self-made millionaire, built his home in 1869 on land his family had homesteaded since 1855. In 1901, his son Milton, a partner in the William Curry and Sons Company, bought the property from the heirs and largely demolished it, preserving only the cookhouse to create the Georgian Revival mansion that stands today. The remaining brick chimney and tiled hearth once housed a wood-burning stove, where the mysterious "Aunt Sally" is believed to have invented the Key West Pie. Recent evidence suggests she was actually Sarah Jane Lowe, wife of William's oldest son, Charles.

Pass by without stopping

Key West First Legal Rum Distillery

105 Simonton St, Key West, 33040-6626, Florida

The Florida Keys boast a rich history of rum running dating back to Prohibition, when smuggling rum from the Caribbean into the U.S. became a thrilling and profitable venture. The maze-like waterways, remote islands, and vibrant atmosphere of Key West made it a perfect hub for these daring exploits. Inspired by this adventurous past, Key West First Legal Rum Distillery crafts exceptional rums that embody the spirit of that legendary era.
Originally built in 1900 as Jack's Saloon, the building served as a lively bar before becoming a Coca-Cola bottling facility in 1903—cheers to that classic Rum & Coke! Since opening in 2012, Key West First Legal Rum Distillery has proudly bottled up the essence of Key West, continuing its storied legacy.

10 minutes

St. Paul's Episcopal Church

401 Duval St, Key West, 33040-6550, Florida

Saint Paul's Episcopal Church in Key West, Florida, was founded in 1832 as a mission church for the area's growing population of sailors and merchants. Officially consecrated in 1836, it has been a vital part of the community ever since.
Originally built in Gothic Revival style, the church has undergone various renovations, with the current structure completed in 1910 after a fire. Known for its beautiful stained glass windows and bell tower, Saint Paul's also emphasizes social justice and community outreach, serving as a gathering space and a lasting symbol of faith in Key West.

7 minutes