Walking tours in Key West pack plenty of worthwhile sightseeing into this compact Florida island.
The Southernmost Food and Cultural Walking Tour stands out for its excellent sampling of local flavors – from fresh-caught seafood to authentic Cuban dishes and the island’s famous key lime pie.
For history enthusiasts, the Historic Homes and Island History tour effectively covers the must-see landmarks while sharing fascinating stories of the island’s past.
Ghost tours after dark and themed music walks (including a fun Margaritaville-inspired route) round out the offerings.
Let’s explore the top walking tours worth your time and money in Key West.
Key Points
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Key West offers a range of comprehensive walking tours that cater to diverse interests, including culinary, historical, cultural, and themed experiences.
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Highly recommended culinary walking tours include the Key West Southernmost Food and Cultural Walking Tour and the Key West Historic Seaport Food Tasting and Cultural Walking Tour.
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Popular historical and cultural walking tours, such as the Key West Historic Homes and Island History – Small Group Walking Tour and the Highlights and Stories of Key West – Small Group Walking Tour, provide in-depth exploration of Key West’s rich heritage.
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Themed walking tours, like the Ghosts of Key West Walking Tour and the Key West Haunted Pub Crawl Walking Tour, offer unique experiences focused on the city’s haunted history and local culture.
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For a self-guided tour option, Key West’s Self Guided Ghost Walking Tours allow travelers to explore the city’s ghostly past at their own pace using a smartphone-guided experience.
Key West Southernmost Food and Cultural Walking Tour
The Key West Southernmost Food and Cultural Walking Tour offers a delightful exploration of the city’s culinary and historical highlights.
This 1.2-mile guided walking tour takes groups of up to 12 travelers through the charming Old Town district, stopping at mom-and-pop eateries to sample local specialties like seafood, Cuban cuisine, key lime pie, and rum cocktails.
Along the way, the knowledgeable guide shares insights about Key West’s food, architecture, and history.
With a 98% traveler recommendation and over 1,300 positive reviews, this tour provides a unique opportunity to discover the city’s vibrant culture and flavors off the beaten path.
The tour is wheelchair and stroller accessible, making it suitable for a wide range of visitors.
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Key West Historic Seaport Food Tasting and Cultural Walking Tour
Offering an immersive culinary and cultural experience, the Key West Historic Seaport Food Tasting and Cultural Walking Tour invites visitors to embark on a captivating exploration of the city’s vibrant heritage.
With a 98% traveler recommendation and a Badge of Excellence, this 5-location tour combines mouthwatering food tastings with a guided walking tour of downtown Key West.
Highlighting the area’s rich history, the knowledgeable and friendly guides enhance the experience, making it suitable for first-time and frequent visitors alike.
Offering accommodations for dietary restrictions, the tour caters to a range of preferences, while the inclusive package, including hotel pickup and drop-off, ensures a seamless and memorable journey.
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Key West Historic Homes and Island History – Small Group Walking Tour
Visitors seeking a deeper understanding of Key West’s captivating history and architectural heritage can embark on the Key West Historic Homes and Island History – Small Group Walking Tour.
Led by knowledgeable guides, this 10 am walking tour explores the island’s unique landmarks and historic homes, including the Casa Antigua, Curry Mansion Inn, and Truman Annex Park.
With a maximum group size of 12, the tour provides an intimate and engaging experience, allowing travelers to learn the stories behind these significant sites.
The tour is accessible, with rain ponchos and umbrellas provided if needed, and positive reviews praise the depth of historical and architectural insights offered by the guides.
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Highlights and Stories of Key West – Small Group Walking Tour
This engaging small-group walking tour provides travelers an immersive exploration of Key West’s captivating history, culture, and landmarks.
Led by a knowledgeable local guide, the tour focuses on the island’s diverse heritage, from legendary tales to iconic sites. Guests will visit the Audubon House, the Southernmost Point, and the US 1 Mile Marker 0, all while learning about Key West’s unique biodiversity and vibrant community.
With a maximum of 10 travelers, this personalized experience offers rain ponchos, restaurant recommendations, and flexibility to cater to various accessibility needs.
Highly recommended by past visitors, this tour is an excellent way to kickstart a memorable trip to this Florida Keys destination.
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Key West Historic District Small-Group Walking Tour
What better way to take in Key West’s rich history than through a guided small-group walking tour of the Historic District?
The Key West Historic District Small-Group Walking Tour offers an engaging 2-hour experience covering 1.4 to 1.8 miles. Led by knowledgeable local guides, this tour showcases famous landmarks and hidden gems, while sharing insightful stories about the city’s history, lore, and legends.
With a maximum group size of 10 guests, the experience ensures a crowd-free atmosphere. Rated 5.0 out of 233 reviews, this tour comes highly recommended and has earned a Badge of Excellence from Florida Keys Ventures.
Comfortable walking shoes and hydration are advised for this moderate-level tour.
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Key West Walking Food Tour With Secret Food Tours
Enjoy Key West’s culinary delights with the Key West Walking Food Tour by Secret Food Tours. This highly-rated walking tour explores the island’s neighborhoods and history while treating you to a variety of local specialties.
From Cuban cuisine and conch fritters to chocolate-dipped key lime pie, you’ll savor generous portions of the region’s signature dishes. While the tour boasts a 96% traveler recommendation, some guests noted inconsistent food quality and a lack of historical context.
The host is committed to improving the experience, including better guide training for more engaging storytelling. With a maximum group size of 12, this food tour is an ideal way for foodies to discover Key West’s flavors.
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The Ghosts of Key West Walking Tour
Exploring Key West’s haunted history, the Ghosts of Key West Walking Tour invites visitors to uncover the island’s spooky past.
This highly-rated 4.5/5 tour takes guests on a captivating 08:00 PM stroll through the historic district, sharing tales of ghostly encounters and mysterious happenings.
Led by knowledgeable local guides, the small group experience (max 30 travelers) provides an engaging mix of island history and supernatural stories.
Though not suitable for those with back issues or expecting, the tour’s moderate fitness level makes it accessible to most.
With free cancellation up to 24 hours prior, this 90-minute tour offers flexibility and value at $24.99 per person, complete with all taxes, fees, and gratuities included.
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Old Key West: Small-Group Jimmy Buffet Walking Tour
The Jimmy Buffett-themed walking tour in Key West offers an immersive glimpse into the iconic musician’s local connections.
Lasting 1.5 hours, the small-group tour explores historical sites related to Buffett’s life and career, including his first gigs and favorite hangouts.
Led by a knowledgeable guide in a neon green shirt, you will enjoy a slice of Key lime pie, visit Mallory Square, and end the experience with alcoholic beverages at Capt Tony’s Saloon.
With high praise from 92% of past travelers, this tour provides an entertaining and informative look at Buffett’s enduring influence on the island city.
Moderate fitness is required, and advance booking is recommended to secure a spot.
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Hemingway Food and Walking Tour
Travelers seeking to uncover the literary legend of Ernest Hemingway in Key West can embark on the captivating Hemingway Food and Walking Tour.
This 2-hour excursion, with a maximum of 15 participants, departs from the Hemingway Home and Museum and concludes at the iconic Capt Tony’s Saloon. Guests will savor a sample menu of local fare, including chicken street tacos and conch fritters, along with dessert and alcoholic beverages.
Knowledgeable guides, such as Caleb and Liz, provide engaging historical insights and personal anecdotes about Hemingway’s time in the city.
With a 92% recommendation rate and a Badge of Excellence, this tour offers an immersive experience for $99 per person, requiring a moderate fitness level for approximately 3 miles of walking.
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Key West Haunted Pub Crawl Walking Tour
For those seeking a chilling yet captivating experience in Key West, the Key West Haunted Pub Crawl Walking Tour offers a unique opportunity to uncover the city’s ghastly past.
Guided by knowledgeable hosts, the 2-hour tour takes guests on a spooky journey through Key West’s haunted hotspots, complete with stops at local pubs for included alcoholic beverages.
With a maximum of 20 travelers, the tour provides an intimate setting for exploring the city’s dark history and supernatural tales.
While not wheelchair accessible or recommended for pregnant individuals, the tour has received high praise for its engaging storytelling and atmospheric pub visits, making it a must-do for those drawn to the paranormal side of Key West.
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PRIVATE Key West Haunted History Walking Tour
Intrigue and paranormal curiosity lure guests to embark on the PRIVATE Key West Haunted History Walking Tour.
Recommended by 100% of travelers and boasting a 5.0 rating, this 2.5-hour excursion unveils the haunted secrets of the island city.
Beginning at Bearded Lady Key West, guests follow a knowledgeable guide through the historic downtown, learning about the area’s eerie past and encountering ghostly tales.
The tour concludes near Captain Tony’s Saloon, allowing easy access to other popular haunts.
With a start time of 7:30 PM, this private experience caters to small groups, ensuring an intimate atmosphere.
Wheelchair-accessible and near public transportation, the tour accommodates most travelers seeking a supernatural adventure in Key West.
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Private Highlights and Stories of Key West Walking Tour
The Private Highlights and Stories of Key West Walking Tour offers a comprehensive exploration of the island’s storied past.
With a 5.0 overall rating from 8 reviews, this private tour allows your group to discover the city’s top attractions and hear captivating tales from a professional, friendly guide.
The tour starts at the Mel Fisher Maritime Museum and ends at the Southernmost House Hotel, covering a manageable walking distance.
Enjoy rain protection, bottled water, and restaurant recommendations, as well as the option to purchase alcoholic beverages.
While travelers with back problems or serious medical conditions should avoid this tour, it’s accessible for those with service animals, strollers, and wheelchairs.
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Private Key West Historic Homes and Island History Walking Tour
Enjoy the captivating history of Key West on the Private Key West Historic Homes and Island History Walking Tour.
This highly-rated, 5-star tour provides an in-depth exploration of the island’s past through its charming historic homes and stories.
Led by a professional, friendly guide, the tour includes rain protection, bottled water, and restaurant recommendations.
Wheelchair accessible and near public transportation, the tour is a moderate physical activity level.
Confirm your booking within 48 hours, and take advantage of the Lowest Price Guarantee.
Whether you’re a history buff or simply want to discover Key West’s unique character, this private tour promises an unforgettable experience.
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Key West’s self-guided ghost walking tours, powered by the WalknTours smartphone application, offer a captivating way to explore the island’s haunted past.
The tour is accessible through a private, smartphone-guided experience, with no in-person guide. Participants can start at Captain Tony’s Saloon and end at the iconic Sloppy Joe’s Bar, taking in the island’s spooky history along the way.
The tours are available daily from 12:00 AM to 11:30 PM, with a duration of up to 12/3/2025. While not wheelchair accessible, the tours are suitable for most travelers.
User reviews praise the ease of use and the well-researched historical context, though some note the need for multi-language support.
Read our full review: Key Wests Self Guided Ghost Walking Tours Smartphone Navigated on WalknTours Review
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Florida Key West Self-Guided Walking Audio Tour
Dive into the captivating history and vibrant culture of Key West with the Florida Key West Self-Guided Walking Audio Tour. Offered by Drive with Action, this engaging walking tour provides an immersive experience through the city’s iconic landmarks.
Enjoy high-quality narration and thrilling tales as you explore at your own pace. The comprehensive route ensures you don’t miss any highlights, and the hands-free GPS functionality allows you to focus on your surroundings.
With a 5.0-star rating from 6 reviews, this tour offers an exceptional value for those seeking a unique and personalized adventure in Key West.
Consider bundling it with the Ultimate Florida Self-Guided Driving Audio Tour for an unforgettable exploration of the Sunshine State.
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Key West: Hemingway’s Life and Local Food Walking Tour
For those seeking a deeper exploration of Key West’s rich history and culture, the Key West: Hemingway’s Life and Local Food Walking Tour offers an immersive experience.
Priced at $99 per person, this 2-hour English-language tour guides visitors through Hemingway’s former stomping grounds, stopping at significant landmarks and allowing them to sample local specialties.
Highlights include visiting the Hemingway House, learning about the author’s activities, and enjoying three food tastings.
With a 5/5 rating based on customer reviews, this tour promises an engaging and informative journey through Key West’s past, bringing Hemingway’s legacy to life.
Comfortable attire and shoes are recommended, as the moderately paced tour covers multiple locations.
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Key West: Southernmost Food and Cultural Walking Tour
Travelers seeking a deeper immersion into Key West’s vibrant Cuban and Caribbean influences will find the 3-hour “Southernmost Food and Cultural Walking Tour” a compelling option.
Priced at $2,166 per person, this small-group tour (limited to 7 participants) offers an engaging experience, including five local food tastings, a guided walk through historic neighborhoods, and exclusive recipes and recommendations.
With a knowledgeable local guide, you will explore Key West’s hidden gems, learn about its history and culture, and enjoy dishes like conch fritters and key lime pie.
Wheelchair accessible and weatherproof, the tour provides an immersive and memorable journey through the Southernmost city’s unique culinary and cultural landscape.
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Key West: Food Tasting and Cultural Walking Tour
The Key West: Seafood and Seaport Walking Tour with 6 Tastings offers a captivating exploration of the island’s culinary heritage and historic waterfront.
Priced at $90.19 per person, this 3-hour walking tour showcases 6 local seafood specialties from hidden eateries and family restaurants.
Led by a knowledgeable local guide, you will cover 1.5 miles while learning about Key West’s history, culture, and the significance of conch as an island delicacy.
The tour includes complimentary e-guides, recipes, and shopping privileges, providing an immersive and personalized experience.
With a maximum group size of 7, the tour ensures an intimate and enjoyable outing, as evidenced by its outstanding 4.9/5 rating based on 34 reviews.
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Key West: Jimmy Buffet Walking Tour With Key Lime Pie
Embarking on a captivating journey through the vibrant streets of Key West, the Jimmy Buffett Walking Tour offers an immersive exploration of the singer-songwriter’s deep connections to this island paradise.
Priced at $79 per person, the 1.5-hour tour takes participants to key sites that inspired Buffett’s iconic songs, including the location of his first gig, his recording studio, and the legendary Margaritaville.
Along the way, guests savor a slice of authentic Key Lime pie and an alcoholic beverage, while learning about Buffett’s life and his enduring relationship with Key West.
With an overall rating of 4.5/5, this tour promises an engaging and unforgettable experience for Parrotheads and casual visitors alike.
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Key West: History and Culture Southernmost Walking Tour
Immersing oneself in Key West’s rich history and vibrant culture is an enthralling experience through the Southernmost Walking Tour. Priced at €37.97 per person, this 1.5-hour excursion led by a local guide offers an insightful exploration of the island’s past.
Participants can expect to learn about Key West’s prosperous shipwrecking, sponge harvesting, and cigar manufacturing industries that made it one of the wealthiest cities in the mid-1800s.
The tour starts at Kino Sandals Plaza and ends at the iconic Southernmost Point buoy, with free maps provided for further independent exploration. Rated 4.9/5 based on 9 reviews, this walking tour is suitable for all ages and traveler types, with comfortable attire and water recommended.
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Break Down
Key West offers a variety of walking tours that allow visitors to explore the island’s rich history, vibrant culture, and delectable cuisine. Whether you’re interested in food, architecture, or local stories, there’s a tour to suit your interests. With knowledgeable guides and immersive experiences, these tours provide an engaging and memorable way to discover the unique charms of this iconic Florida destination.