• San Carlos Institute - Located in Key West, Florida, the San Carlos Institute is a historic cultural and educational center founded in 1871. It functions as a museum, library, art gallery, theater, and school, with a primary focus on preserving and promoting Cuban heritage and culture. The institute was instrumental in Cuba’s independence movement, as it was here that José Martí united the Cuban exile community in 1892 to initiate his independence campaign.

The San Carlos serves as a hub for cultural events, hosting various art exhibitions, performances, and educational programs, making it a lively community center. Its architectural style reflects late 19th-century influences, and it remains a symbol of the strong ties between Key West and Cuba. The institute continues to be a vital part of the local landscape, celebrating the rich history and contributions of Cuban immigrants in the area.

• Duval Street - A stroll through the heart of Key West’s party central, the renowned Duval Street.
• Capt Tony’s Saloon - The building at 428 Greene Street boasts a vibrant history that mirrors Key West itself. Originally built in 1851 as an ice house and morgue, it later served as a wireless telegraph station during the Spanish-American War and housed a cigar factory and bordello. After a brief period as the Duval Club, known for its extravagant parties that attracted Navy attention, 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 spot 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.”

• The Studios of Key West - The Studios was established to connect world-class artists with local audiences and inspire creativity. It has welcomed Pulitzer Prize winners and renowned musicians, introducing thousands of students to diverse artistic perspectives. The 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.
• Curry Mansion Inn - 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, purchased 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.
• Key West First Legal Rum Distillery - The Florida Keys have a rich history of rum running dating back to Prohibition, when smuggling rum from the Caribbean into the U.S. became an exciting and profitable venture. The maze-like waterways, remote islands, and vibrant atmosphere of Key West made it an ideal 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.

• St. Paul’s Episcopal Church - 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.

• Local Tour Guide

Join an engaging walking tour of the Key West Historic District, where every step unveils fascinating stories and hidden treasures. Explore iconic buildings with rich histories, discovering tales of vibrant personalities who shaped the island, from famous writers to influential locals.

As participants wander through beautifully preserved architecture, they will gain insights into the importance of each site, connecting with the spirit of Key West. This tour provides an opportunity to experience the island’s essence through its rich stories, creating an unforgettable adventure filled with intrigue and nostalgia. Don’t miss this enchanting journey!

For a full refund, cancel at least 24 hours before the scheduled departure time.