Key West Odyssey: Uncover Island Secrets, Walk by Locals

Key West, US
100% of travellers recommend this
Excellent (2 reviews)
Self-guided

Included

  • inclusion
    Other
    Local Tour Guide

Meeting Point

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

Meeting point

518 Duval St, Key West, FL 33040 , United States

End point

End Point

Schooner Wharf began on the Schooner Diamante and is now a beloved bar with rustic charm and a second-floor deck overlooking Key West's Historic Seaport. It attracts celebrities like Mel Fisher and Charles Kurault. Voted Best Local's Bar and featured in magazines like New York Times

Meeting point

202 William St, Key West, FL 33040 , United States

End point

What to expect

1
San Carlos Institute

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.

Duration 10 minutes
2
Duval Street

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

3

Capt Tony’s Saloon

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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."

Duration 10 minutes
4
The Studios of Key West

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.

Duration 10 minutes
5

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, 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.

6
Key West First Legal Rum Distillery

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.

Duration 10 minutes
7
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.

Duration 7 minutes

The experience can be subject to change due to bad weather or unforseen circumstances. We always endeavour to give you the best possible experience.

Additional Information

  • Additional information
    Infants and small children can ride in a pram or stroller
  • Additional information
    Public transportation options are available nearby
  • Additional information
    Service animals allowed
  • Additional information
    Suitable for all physical fitness levels
Provided by Florida Keys Ventures

What our experts say

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    Visit Sloppy Joe’s nearby post-tour.
  • icon
    Try a slice of Key Lime Pie at Kermit’s.
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    Explore the San Carlos Institute after.
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    Check out local art at The Studios.
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    Bring water; stay hydrated in the sun.

More About this Experience

Introduction

Embark on a captivating journey through the Key West Historic District with Key West Odyssey, a guided walking tour exploration like no other. Step back in time and immerse yourself in the rich history and vibrant culture of this iconic island paradise.

What to expect?

During the Key West Odyssey tour, participants can look forward to delving into the fascinating stories and hidden gems of the Key West Historic District. From exploring historic buildings to learning about the colorful figures who have left their mark on the island, every step promises to be filled with intrigue and discovery.

Who is this for?

This tour is perfect for history buffs, adventure seekers, and anyone with a curiosity for the past. Whether you're a solo traveler, a couple looking for a unique experience, or a group of friends wanting to explore Key West in a new way, Key West Odyssey offers something for everyone.

Why book this?

Key West Odyssey stands out as a one-of-a-kind experience that allows you to truly connect with the spirit of Key West. With knowledgeable local guides leading the way, you'll uncover the island's hidden stories and gain a deeper appreciation for its history. This immersive tour promises to create lasting memories and a sense of nostalgia for the beauty and charm of Key West.

Good to know

Participants should wear comfortable shoes and bring along a camera to capture the stunning architecture and picturesque surroundings. The tour concludes at Schooner Wharf, a beloved local bar with a rich history and a vibrant atmosphere, perfect for relaxing and reminiscing about the day's adventures.

Reviews

Travelers rave about the Key West Odyssey experience, praising the knowledgeable guides, engaging storytelling, and the unique insights gained during the tour. Many have described it as a highlight of their Key West visit, offering a deeper understanding of the island's past and present. Joining the Key West Odyssey tour promises an unforgettable and enriching exploration of this historic gem.

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