Key West Odyssey: Uncover Island Secrets, Walk by Locals
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Key West Odyssey: Uncover Island Secrets, Walk by Locals

Active
1h
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Mobile or paper ticket accepted

About this experience

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!

Available options

Key West Odyssey: Uncover Island Secrets, Walk by Locals

What's included

Local Tour Guide

Detailed itinerary

1

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.

2
Stop 2 Pass by

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

3

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."

4

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.

5

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

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.

7
Stop 7

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.

Available languages

Guide guide
EN

Important information

Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels

Meeting point

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

Important notes

Show your ticket to the guide

About Key West

Key West is a vibrant island city known for its tropical climate, rich history, and laid-back atmosphere. As the southernmost city in the continental U.S., it offers a unique blend of Caribbean and American cultures, stunning beaches, and a thriving arts scene.

Top Attractions

Duval Street

The heart of Key West's nightlife and shopping, Duval Street stretches from the Gulf of Mexico to the Atlantic Ocean, offering a mix of bars, restaurants, shops, and galleries.

Entertainment Half day to full day Free to explore, costs vary for attractions and dining

Dry Tortugas National Park

A remote and pristine national park accessible only by boat or seaplane, featuring Fort Jefferson and stunning coral reefs for snorkeling and diving.

Nature Full day trip Ferry: $185-$220, Seaplane: $300-$350, Park entry: $15 per person

Key West Butterfly and Nature Conservatory

A lush tropical garden filled with free-flying butterflies, birds, and other wildlife, offering a serene and educational experience.

Nature 1-2 hours $22 for adults, $12 for children (6-17)

Must-Try Local Dishes

Key Lime Pie

A tangy and sweet pie made with key lime juice, egg yolks, and sweetened condensed milk, topped with whipped cream or meringue.

Dessert Contains dairy and eggs, can be made gluten-free

Conch Fritters

Deep-fried fritters made with conch meat, vegetables, and spices, served with a dipping sauce.

Appetizer Contains seafood, can be made gluten-free

Grouper Sandwich

A sandwich featuring fresh local grouper, often blackened or fried, served on a toasted bun with lettuce, tomato, and tangy sauce.

Lunch Contains seafood, can be made gluten-free

Popular Activities

Snorkeling Diving Kayaking Paddleboarding Fishing Beach lounging Spa treatments Sunset cruises

Best Time to Visit

November to April

This is the most popular time to visit Key West, with pleasant weather and lower humidity. It's ideal for outdoor activities and festivals.

21-28°C 70-82°F

Practical Information

Language

  • Official: English
  • Widely spoken: Spanish
  • English: Widely spoken

Currency

U.S. Dollar (USD)

Time Zone

Eastern Time Zone (ET) (UTC-5:00, UTC-4:00 during daylight saving time)

Electricity

120VV, 60HzHz

Safety Information

Overall Safety Rating: Generally safe

Key West is generally a safe destination for travelers, with low violent crime rates. However, petty crime, such as pickpocketing and theft, can occur in tourist areas. Exercise caution and common sense to ensure a safe and enjoyable trip.

Important Precautions:
  • • Keep valuables secure and out of sight
  • • Use ATMs located inside banks or reputable establishments
  • • Be cautious when using public transportation or taxis, and always use licensed services

Getting there

By air
  • Key West International Airport • 4 miles from downtown

Getting around

Public transport

Affordable and convenient, with multiple routes serving popular destinations.

Taxis

Available • Apps: Uber, Lyft

Rentals

Car, Bike, Scooter

Neighborhoods

Old Town New Town

Day trips

Dry Tortugas National Park
70 miles by ferry or 30 minutes by seaplane • Full day

A remote and pristine national park featuring Fort Jefferson and stunning coral reefs for snorkeling and diving.

Big Pine Key
30 miles north of Key West • Half day to full day

A scenic island known for its pine rocklands, wildlife, and the famous Key deer.

Looe Key Reef
5 miles west of Big Pine Key • Half day to full day

A popular snorkeling and diving spot featuring a vibrant coral reef and diverse marine life.

Festivals

Fantasy Fest • Late October Key West Food and Wine Festival • Early November Key West Highlight Film Festival • Early November

Pro tips

  • Visit Mallory Square for the famous sunset celebrations, which feature street performers, local vendors, and stunning views of the sunset.
  • Explore the island by bike or scooter, as it's a great way to get around and see the sights.
  • Try key lime pie, a local specialty made with fresh key limes and sweetened condensed milk.
  • Visit the Key West Butterfly and Nature Conservatory, a lush tropical garden filled with free-flying butterflies, birds, and other wildlife.
  • Take a day trip to Dry Tortugas National Park, a remote and pristine island featuring Fort Jefferson and stunning coral reefs for snorkeling and diving.
From $25 per person

Price varies by option

Adults
Age 13-100
1
Childs
Age 7-11
0
Infants
Age 0-6
0
Booking requirements:
  • Min travelers: 1
  • Max travelers: 10
  • Adult required for booking
Secure booking
Free cancellation available
Instant confirmation

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