Key West’s historical tours offer efficient ways to discover this Florida island’s fascinating past. The most worthwhile options include the Historic Seaport food walks, which combine local cuisine with maritime stories, and the evening ghost tours that bring the island’s spooky tales to life through historic buildings and graveyards. The architectural walking tours stand out for their excellent coverage of the island’s distinctive 19th-century buildings and famous residents. Small-group history tours provide intimate looks at both well-known landmarks and hidden corners, while the Black history tours reveal important but often overlooked stories of the island’s past. Let’s explore the best historical tours Key West has to offer.
Key Points
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The Southernmost Walking Tour offers a 1.5-hour exploration of Key West’s storied past, covering the southernmost point and providing engaging historical insights.
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The Private Haunted History Walking Tour takes visitors to at least five haunted mansions and two haunted bars, providing a chilling glimpse into the city’s paranormal legacy.
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The Historic Homes and Architecture Tours offer a personalized experience, showcasing architectural gems and captivating tales of Key West’s past, with knowledgeable guides and a maximum of 12 travelers.
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The Historic Homes and Island History Walking Tour provides a personalized exploration of Old Town neighborhoods, featuring sites like the Audubon House, Tropical Gardens, and Truman Annex Park.
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The Cruise Through Black History Audio Tour offers an immersive experience, highlighting Key West’s rich Black history, including its connection to the Bahamas and role in defeating the Confederacy.
Historic Seaport Food & Walking Tour by Key West Food Tours
The Historic Seaport Food & Walking Tour by Key West Food Tours immerses visitors in the rich culinary and cultural heritage of this iconic Florida destination.
Over the course of the moderate-paced tour, guests sample locally caught seafood, such as pink shrimp and spiny lobster, as well as non-seafood options at 5 locations. The experience includes a glass of white wine and the famous Key lime pie.
Professionally-trained guides provide insights into Key West’s history and culture, with highlights including fish tacos, shrimp cocktail, Cuban sandwich, and lobster mac and cheese.
With 551 total reviews and a 98% recommendation rate, this tour offers a unique and delightful way to discover the flavors of Key West.
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Key West: History and Culture Southernmost Walking Tour
Key West’s Key West: History and Culture Southernmost Walking Tour immerses visitors in the rich tapestry of the island’s captivating past.
Priced at $39.99 per person, this 1.5-hour walking tour takes guests on a journey through Key West’s storied history, from shipwrecking and sponge harvesting to cigar manufacturing.
Led by a local guide, the tour explores the southernmost point of the continental U.S. and provides free maps for further exploration.
With an overall rating of 4.9/5, the tour is praised for its informative content, engaging presentation, and helpful dining and entertainment recommendations.
Suitable for all age groups, the tour operates rain or shine and covers a distance of 1.4-1.8 miles.
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Parasailing Over the Historic Key West Seaport
Soaring over the historic Key West Seaport, parasailing offers visitors an exhilarating aerial experience that provides a unique perspective on the island’s rich maritime heritage.
Operated by Sunset Watersports, the activity accommodates singles, doubles, and triples, making it ideal for groups and families.
With multiple tour times available, the 74.95 USD per-person experience lasts for an enjoyable duration and includes gratuities.
While not wheelchair accessible, the activity’s safety-focused approach and friendly staff ensure a memorable outing, as evidenced by the impressive 4.5-star rating from 170 customer reviews.
Whether seeking a thrill or simply admiring the coastal views, parasailing is a top recommendation for visitors to Key West.
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Key West Historic Homes and Island History – Small Group Walking Tour
Delving into the architectural gems and captivating tales of Key West’s storied past, the Key West Historic Homes and Island History – Small Group Walking Tour offers visitors an immersive experience.
Praised for its knowledgeable guides and engaging storytelling, the tour explores notable historic sites, including the Casa Antigua, Curry Mansion Inn, and Truman Annex Park.
With a maximum of 12 travelers, the small-group format ensures a personalized and insightful journey through Key West’s rich history and unique architecture.
Whether a first-time visitor or a returning guest, this tour is highly recommended as an excellent investment in understanding the island’s captivating legacy.
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Key West Historic District Small-Group Walking Tour
The Key West Historic District Small-Group Walking Tour offers visitors an immersive exploration of the island’s captivating past. Guided by knowledgeable locals like AJ, the tour covers 1.4 to 1.8 miles of the historic district, providing insights into Key West’s unique architecture, cultural influences, and significant landmarks.
The small group size ensures a more intimate experience as travelers learn about the island’s cigar-making heritage and receive recommendations for dining and attractions.
With high ratings and a Badge of Excellence, this two-hour tour is a must-do for those seeking an authentic and informative introduction to Key West’s rich history.
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Sunset Sail on Historic Schooner in Key West
One of the best ways to experience the historic charm of Key West is aboard the Sunset Sail on Historic Schooner. This 5-star rated activity offers travelers a beautiful sunset cruise on a classic schooner previously owned by General Patton.
With a maximum of 28 guests, the intimate sailing experience features stunning views, complimentary beverages, and a knowledgeable crew skilled in handling the historic vessel.
While some travelers noted maintenance needs, the overall feedback is overwhelmingly positive, praising the excellent service and memorable atmosphere.
At $109 per person, the Sunset Sail is a must-do for those seeking a unique and picturesque way to explore Key West’s maritime history.
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Florida Keys Nature & History Tour From Key West
Exploring the diverse natural landscapes and rich history of the Florida Keys, the Florida Keys Nature & History Tour from Key West offers an immersive experience for travelers.
Rated 97% recommended by past guests, this small-group tour takes visitors on a journey across the Overseas Highway, stopping at Bahia Honda State Park, the National Key Deer Refuge, and the Blue Hole.
Along the way, guests can spot wildlife like key deer and alligators, and learn about the region’s fascinating history.
With hotel pickup, snacks, and National Park fees included, the tour provides a convenient and informative way to discover the natural wonders of the Florida Keys.
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Southernmost Key West History and Culture Small-Group Walking Tour
Departing from the Kino Sandals Factory plaza in Key West’s Old Town, the Southernmost Key West History and Culture Small-Group Walking Tour takes visitors on a captivating exploration of the island’s rich past and vibrant present.
Covering approximately 1.4 to 1.8 miles at a moderate pace, this 99% traveler-recommended tour showcases the city’s highlights, including the Ernest Hemingway Home and Museum, Southernmost Point, and Audubon House & Tropical Gardens.
Led by a local guide with extensive knowledge, the tour provides engaging historical context and personal anecdotes, enhanced by the use of an iPad for visual storytelling.
With a maximum group size of 10, this 5.0-rated, Badge of Excellence tour offers an immersive and personalized experience for $39.99 per person.
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Key West Conch Train Tour: Explore Iconic Sights and History
The Key West Conch Tour Train offers visitors a captivating and iconic sightseeing experience of the island’s top attractions.
This 1.5-hour narrated train ride takes guests on a journey through Key West’s history, paying tribute to Henry Flagler’s legendary railway.
Riders enjoy free admission to the Sails to Rails Museum, two walking tours, a full-color map, and discount coupons.
The tour departs daily from the Front Street Depot and returns to the same location.
Praised for its knowledgeable and entertaining guides, the Conch Tour Train is a must-do activity for those seeking a unique and informative exploration of Key West’s charms.
With convenient accessibility and flexible booking options, it’s a popular choice among visitors.
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Key West Art History Private Tour
For those seeking a more intimate and immersive exploration of Key West’s vibrant art scene, the Key West Art History Private Tour offers a captivating experience.
Rated 5.0 out of 33 reviews, this private tour takes participants on a curated path through the city’s art exhibitions, allowing them to engage with local artists and gain insightful commentary from knowledgeable guides.
The tour starts at the Key West Museum of Art & History and ends at The Studios of Key West, ensuring an immersive journey into the heart of the island’s artistic community.
Wheelchair accessible and suitable for most travelers, this tour provides a unique opportunity to explore Key West’s rich art history.
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PRIVATE Key West Haunted History Walking Tour
Set out on a spooky journey through Key West’s haunted history with the PRIVATE Key West Haunted History Walking Tour.
With a 5.0 overall rating and 100% traveler recommendation, this exclusive tour promises a personalized experience.
Led by a knowledgeable guide, you’ll visit at least five haunted mansions and two haunted bars, where you’ll hear chilling tales of the paranormal.
The tour meets at the Bearded Lady and concludes near Duval & Green Street, close to Captain Tony’s Saloon.
Accessible to most travelers, this tour offers a lowest price guarantee and free cancellation up to 24 hours in advance, making it a must-do for anyone seeking a thrilling glimpse into Key West’s haunted past.
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Private Key West Historic Homes and Island History Walking Tour
Key West’s historic homes and island history come alive on this private walking tour.
Explore Old Town neighborhoods at your own pace, visiting notable sites like the Audubon House, Tropical Gardens, Truman Annex Park, and Casa Antigua.
Your personal guide shares captivating stories and architectural insights not found in guidebooks. The flexible pace allows for stopping at your leisure, and the tour includes hotel pickup and drop-off, rain ponchos, umbrellas, and bottled water.
With a 5.0 overall rating from 6 reviews, this tour provides a unique and immersive experience for those interested in Key West’s rich history and architecture.
Moderate fitness is required, and alcoholic beverages are available for purchase.
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Cruise Through Key Wests Black History Audio Tour
Visitors can discover the rich Black history of Key West through this self-guided audio tour. The tour covers the island’s connection to the Bahamas and its role in defeating the Confederacy.
Significant sites include a cemetery where 250 Africans are laid to rest by the beach and an exclusive blacks-only beach. The tour also features culinary experiences, such as conch salad and key lime pie.
The tour is accessible, with wheelchair and stroller access, and it can be downloaded to a phone or tablet. With an overall rating of 5.0 from 8 reviews, the tour offers a comprehensive and engaging exploration of Key West’s Black history.
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Haunted Historic Firehouse Ghost Tour
The Haunted Historic Firehouse Ghost Tour offers visitors a chilling and captivating exploration of Key West’s haunted past. Operated by Ghost Key West, this tour invites guests to experience the creepy elements of a historic haunted firehouse, including fast-moving shadows and energy detection.
Participants may even have personal experiences with SLS equipment. The tour includes after-hours admission to the firehouse, a day pass to the Firehouse Museum, and optional access to a haunted fire truck for an in-cab EVP session.
With consistently positive reviews and a 5.0 rating, this tour is suitable for most travelers, though it’s not wheelchair accessible. Those seeking a unique historical encounter will find the Haunted Historic Firehouse Ghost Tour a thrilling experience.
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Southernmost Key West Historical Tour in Small Group
This intimate Southernmost Key West Historical Tour in a small group offers a captivating exploration of the city’s rich history and landmarks.
Priced at $30 per person, the tour takes visitors on a journey to the southernmost point of the continental United States, with a maximum group size of 10 travelers.
The tour is wheelchair and stroller accessible, and service animals are allowed.
While the tour has received an overall rating of 3.0 based on a few reviews, one notable issue was a no-show by the tour guide on December 26, 2019.
The tour provides a unique opportunity to discover Key West’s historical sites, including the iconic Key West Lighthouse and Ernest Hemingway’s house.
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Frequently Asked Questions
Can I Bring My Own Food on the Walking Tours?
Most walking tour operators allow guests to bring their own snacks and non-alcoholic beverages. However, it’s best to check with the specific tour company beforehand to ensure their policy on outside food and drinks.
What Is the Minimum Number of Participants Required for a Private Tour?
The minimum number of participants required for a private tour varies by tour company, but is typically between 2-4 people. Some companies may offer private tours for a single participant, but this often comes at a higher cost.
Are the Tours Wheelchair Accessible?
The tours are generally wheelchair accessible, with most companies offering accommodations for guests with mobility challenges. Guests should inquire about specific accessibility features when booking to ensure the tour meets their needs.
Can I Take Photos During the Tours?
Typically, visitors are allowed to take photos during historical tours, though some locations may have restrictions. It’s best to check with the tour operator beforehand to ensure you can capture the experience as you wish.
Do the Tours Provide Any Recommendations for Post-Tour Activities?
The tours often provide recommendations for post-tour activities, such as visiting nearby museums, restaurants, or other historical sites. Guests can inquire about these suggestions during the tour to make the most of their time in the area.
The Sum Up
Key West’s historic tours offer visitors a chance to explore the island’s rich past. From food and walking tours to haunted ghost tours, there’s something for every interest. Whether you’re interested in architecture, culture, or the paranormal, these tours provide an immersive and educational experience that brings the city’s history to life. With a range of options, visitors can tailor their exploration to their preferences and uncover the unique stories that make Key West such a fascinating destination.