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Key West Odyssey: Uncover Island Secrets, Walk by Locals

2 Reviews 5.00 out of 5 stars Based on 2 traveler reviews collected by Cool Shore Excursions and TripAdvisor |
Recommended by 100% of reviewers
100% of reviewers gave this experience a rating of 4 or higher.
| Key West, USA
Book online or call us

from $60.41 per person

Lowest Price Guarantee
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Don't miss out!
On average, this is booked 33 (0) days in advance.
1 hour 30 minutes (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

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!

What's Included

  • Local Tour Guide

    Meeting Location

    Meeting point

    516 Duval Street
    Key West, FL 33040, USA

    Show on Google Maps

    Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

    End point

    202 William Street
    Key West, FL 33040, USA

    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

    What To Expect

    Book Online

    Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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    Safe & secure Easy breezy Hassle‑free

    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.
    Read more

    10 minutes Admission Ticket Free

    Duval Street (pass by)

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

    Capt Tony’s Saloon

    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."
    Read more

    10 minutes Admission Ticket Free

    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.
    Read more

    10 minutes Admission Ticket Free

    Curry Mansion Inn (pass by)

    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.
    Read more

    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.
    Read more

    10 minutes Admission Ticket Free

    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.
    Read more

    7 minutes Admission Ticket Free

    Show 6 more stops

    Additional Info

    • Confirmation is instant and will be received at time of booking
    • Service animals allowed
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels
    • Infants and small children can ride in a pram or stroller
    • This tour/activity will have a maximum of 10 travelers

    Frequently Asked Questions (7)

    Q: What is the cancellation policy for the Key West Odyssey: Uncover Island Secrets, Walk by Locals?

    A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EST). Read more Apr 2025

    Cancellation Policy

    You can cancel up to 24 hours in advance of the tour for a full refund.

    Still have questions?

    We're here to help.
    Activity code: C-186588P9

    Traveler Photos

    Reviews

    5.00
    2 reviews

    Average 5.00 out of 5 stars based on 2 traveler reviews collected by Cool Shore Excursions and partner sites such as Cool Destinations and TripAdvisor

    5 stars
    2
    4 stars
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    3 stars
    0
    2 stars
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    1 star
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    Don't miss out!
    On average, this is booked 33 (0) days in advance.
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    Frequently Asked Questions (7)

    Activity name

    The answers provided below were previously given in response to questions from Cool Shore Excursions customers.

    Filter by:

    Q: What is the cancellation policy for the Key West Odyssey: Uncover Island Secrets, Walk by Locals?
    A:
    You can cancel up to 24 hours in advance of the tour for a full refund.
    • For a full refund, you must cancel at least 24 hours before the tour start time.
    • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
    • Any changes made less than 24 hours before the tour start time will not be accepted.
    • Cut-off times are based on the tour local time (EST).
    Apr 2025
    Q: What's included in the price?
    A:
    The following is included:
    • Local Tour Guide.
    Apr 2025
    Q: What is the minimum age for this tour?
    A:

    There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..

    Apr 2025
    Q: My date is not available in the calendar, I am just checking to see if it is available?
    A:

    If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

    If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

    Apr 2025
    Q: Is this an accessible tour?
    A:

    Accessibility information for the Key West Odyssey: Uncover Island Secrets, Walk by Locals is as follows:

    • Service animals allowed
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels
    Apr 2025
    Q: Where is the meeting point for this activity?
    A:

    Detailed check-in instructions – including meeting point address, Google map, and parking information – for Key West Odyssey: Uncover Island Secrets, Walk by Locals will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

     

     

    Mar 2024
    Q: How long does a refund take to reach my card, and can I get it faster?
    A:

    Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

    Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

    If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

    Oct 2026

    What's Included

    Activity name

    • Local Tour Guide

    Additional Info

    Activity name

    • Confirmation is instant and will be received at time of booking
    • Service animals allowed
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels
    • Infants and small children can ride in a pram or stroller
    • This tour/activity will have a maximum of 10 travelers

    Report Product Issue

    Activity name