Walking tours in Key West pack a lot of sightseeing value into just a few hours. The island’s compact historic district makes it perfect for exploring on foot. Several excellent guided options stand out: The Southernmost Food & Cultural tour offers the best mix of local eats and stories, while history buffs will appreciate the Historic Seaport walk for its old-time maritime tales. For evening entertainment, the adults-only Dark Side tour delivers spine-tingling ghost stories in a fun, theatrical way. Groups are kept manageably small (usually 8-12 people), and most tours run under 2.5 hours. Let’s explore the top walking tours that showcase the real Key West.
Key Points
- Southernmost Food & Cultural Tour, Historic Seaport Food & Walking Tour, and Caribbean Food Walking Tour offer immersive culinary experiences with high traveler recommendations.
- Key West: History and Culture Tour, Key West Historic Homes Tour, and Key West Historic District Tour provide in-depth insights into the city’s rich history and architecture.
- Dark Side of Key West Tour and Private Key West Haunted History Tour offer unique, engaging experiences exploring the area’s unsettling and paranormal past.
- Tours like Hemingway’s Life and Local Food Tour and Highlights and Stories of Key West Tour blend history, culture, and food for a comprehensive experience.
- Many tours offer accessibility features, flexible scheduling, and positive guest experiences, making them suitable for diverse audiences.
Southernmost Food & Cultural Walking Tour by Key West Food Tours
The Southernmost Food & Cultural Walking Tour by Key West Food Tours offers visitors a delightful exploration of the city’s culinary and cultural heritage.
Covering 1.2 miles, this highly-rated tour (98% recommended) provides a hearty lunch through four food tastings and one alcoholic beverage.
Guided by friendly and knowledgeable locals, the tour takes guests to popular eateries like El Siboney Restaurant and Mangoes Restaurant, where they can savor local dishes, Cuban cuisine, and the classic key lime pie.
With hotel pickup and drop-off, exclusive offers, and all gratuities included, this tour is an excellent way to discover Key West’s vibrant food scene and cultural diversity.
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The Dark Side of Key West Adults Only Walking Tour
On the darker side of Key West, the adults-only walking tour takes visitors on a chilling journey through the city’s haunted past.
For $34.99, guests can explore the island’s haunted sites, learn about true historic events, and hear stories of paranormal activities, grisly murders, and suicides.
Led by knowledgeable guides, the 1.5-hour tour visits notable locations like the Hemingway House and the Artist House, uncovering the influence of historical figures like Count Von Cosel and Robert the Doll.
With an overall rating of 4.3/5, the tour offers great value and an immersive experience, leaving guests with a deeper understanding of Key West’s unique and unsettling history.
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Historic Seaport Food & Walking Tour by Key West Food Tours
Offering a delightful blend of culinary delights and historical insights, the Historic Seaport Food & Walking Tour by Key West Food Tours invites visitors to embark on a savory exploration of the island’s vibrant culinary scene.
With over 550 glowing reviews and a 98% traveler recommendation, this tour provides an immersive experience, showcasing the best of Key West’s locally caught seafood and non-seafood options across 5 tasting locations.
Along the way, participants learn about the area’s rich history and culture, enjoy a glass of white wine and key lime pie, and receive exclusive coupons and recipes.
Suitable for all weather conditions and catering to various dietary needs, this tour offers an engaging and delicious way to discover Key West.
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Key West: History and Culture Southernmost Walking Tour
Immersing visitors in the vibrant history and culture of Key West, the Key West: History and Culture Southernmost Walking Tour provides a captivating 1.5-hour experience.
Priced at $39.99 per person, this guided walking tour takes guests through the island’s past, covering topics like shipwrecking, sponge harvesting, and cigar manufacturing.
Visitors will also reach the Southernmost Point of the continental U.S. and receive free maps to explore further.
With an impressive 4.9/5 rating based on 10 reviews, the tour is praised for its informative, well-paced, and entertaining presentation by guides.
While not suitable for those with mobility impairments, the tour operates rain or shine, making it a flexible and enjoyable way to discover Key West’s rich heritage.
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Key West Historic Homes and Island History – Small Group Walking Tour
The Key West Historic Homes and Island History – Small Group Walking Tour provides visitors with an engaging and informative exploration of the island’s rich past.
Led by knowledgeable local guides, this 5-star rated tour takes guests on a journey through Key West’s most historic homes and neighborhoods.
With a maximum group size of 12, the tour offers an intimate experience highlighting the island’s architecture, social history, and personal anecdotes.
Travelers consistently praise the guide’s expertise and the tour’s ability to enhance their connection to Key West’s unique culture.
Offered daily at 10 AM, this accessible, moderate-intensity tour is a must for anyone seeking to explore the fascinating history of the Southernmost city.
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Key West: Jimmy Buffet Walking Tour With Key Lime Pie
Although Key West is renowned for its vibrant history, it also holds a special place in the heart of music lovers as the adopted home of legendary singer-songwriter Jimmy Buffett.
The “Key West: Jimmy Buffett Walking Tour with Key Lime Pie” offers a unique opportunity to explore the locations that inspired Buffett’s iconic songs and career.
Over 1.5 hours, you’ll visit the site of his first gig, his recording studio, and other iconic spots like Capt. Tony’s Saloon and Margaritaville.
Along the way, you’ll savor a slice of the island’s famous Key Lime pie and a refreshing beverage, all while learning about Buffett’s lasting influence on Key West’s music scene.
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Key West Historic District Small-Group Walking Tour
This 2-hour small-group walking tour offers a captivating exploration of Key West’s Historic District.
Led by the knowledgeable local guide AJ, the tour covers 1.4 to 1.8 miles, with a maximum group size of 20 travelers.
Priced at $46.99 per person, the experience focuses on the district’s rich history, architecture, cultural influences, and unique landmarks.
Guests can expect to see historical bars, cigar factories, and local eateries, while learning about the city’s development and culture through visual aids and engaging commentary.
With a 5.0 rating from 234 reviews, this tour is highly recommended for its informative and enjoyable experience, personalized attention, and insight into Key West’s distinct character.
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Key West: Hemingways Life and Local Food Walking Tour
Hemingway’s legendary life and influence in Key West come alive on this captivating 2-hour walking tour.
Priced at $99 per person, the tour takes visitors on a journey through the iconic writer’s footsteps, visiting his former home, first apartment, and the legendary Sloppy Joe’s bar.
Along the way, participants savor local delicacies like street tacos, conch fritters, and key lime pie.
The knowledgeable guide shares insightful stories about Hemingway’s life, writing, and social activities in the vibrant island town.
With free cancellation up to 24 hours in advance, this tour offers a unique blend of history, culture, and culinary delights, making it a must-do experience for Hemingway enthusiasts and food lovers alike.
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Highlights and Stories of Key West – Small Group Walking Tour
Designed to provide an immersive experience, the Highlights and Stories of Key West – Small Group Walking Tour takes visitors on a captivating journey through the vibrant island’s rich history and local culture.
Led by knowledgeable and engaging guides, this 2-hour walking tour explores Key West’s must-see landmarks and shares unique insights not found in other tours.
With a maximum group size of 10, the tour offers an intimate setting where participants can enjoy the expert commentary, rain or shine, thanks to the provided ponchos and umbrellas.
Highly recommended by past travelers, this tour is an excellent way to start a visit to Key West, providing a perfect blend of history, humor, and local flavor.
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Key West: Caribbean Food Walking Tour
Immersing visitors in the vibrant culinary scene of Key West, the Caribbean Food Walking Tour takes participants on a delectable journey through the island’s diverse flavors.
Rated 4.9 stars out of 5, this 2.5-hour guided tour allows guests to savor a variety of local specialties, from authentic Cuban sandwiches to zesty conch fritters.
Led by knowledgeable guides, the tour explores the lively Duval Street, uncovering the stories and histories behind Key West’s unique gastronomic offerings.
With a small group size, the experience provides an intimate and personalized exploration of the city’s rich food culture.
Priced at €52.11 per person, the Caribbean Food Walking Tour promises an immersive and flavorful adventure for any visitor seeking to discover the tastes of Key West.
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Hemingway Food and Walking Tour
For those seeking to uncover the literary and culinary legacy of Ernest Hemingway in Key West, the Hemingway Food and Walking Tour provides an immersive experience.
This 2-hour, 2-mile walking tour explores the iconic author’s favorite haunts, offering a glimpse into his life through food, culture, and history.
Led by knowledgeable guides, the tour features a sampling of local cuisine, including chicken street tacos and conch fritters, complemented by stops at charming bars and museums.
With a maximum group size of 15, the tour provides an intimate setting for guests to learn and engage.
While not wheelchair accessible, the tour is near public transportation and suitable for moderately fit individuals.
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Key West: Food Tasting and Cultural Walking Tour
The Key West Seafood and Seaport Walking Tour provides an immersive exploration of the island’s rich culinary and cultural heritage.
This 3-hour small-group tour invites guests to sample 6 seafood or drink tastings from local eateries, enough for a hearty lunch.
Led by a knowledgeable guide, the tour delves into Key West’s historic seaport, its architecture, culture, and industrial past.
Participants can also capture photos of the vibrant flora, murals, and landmarks.
Exclusive recipes and an e-guide to Key West’s dining and attractions are included, empowering travelers to recreate the island’s flavors at home.
With a 4.8/5 rating based on 35 reviews, this tour offers excellent value and personalized insights into the local community.
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Key West Walking Food Tour With Secret Food Tours
This comprehensive Key West Walking Food Tour with Secret Food Tours offers an immersive exploration of the island’s diverse culinary landscape. Covering must-try Cuban cuisine, fresh baked cake, conch fritters, and more, the tour showcases the city’s vibrant flavors.
Guests will discover hidden gems, enjoy a variety of tastings, and learn about Key West’s rich history from enthusiastic guides. While primarily focused on food, the tour also provides insights into the island’s charming neighborhoods.
Though some past participants have wished for more historical context, the tour generally receives positive reviews for its engaging guides, diverse offerings, and overall fun experience.
Moderate fitness and proper hydration are recommended for this 3-hour walking excursion.
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Key West: Southernmost Food and Cultural Walking Tour
Exploring Key West’s vibrant culinary and cultural landscape, the Southernmost Food and Cultural Walking Tour immerses guests in the island’s diverse flavors and rich history.
Over the course of 3 hours, a knowledgeable local guide leads a small group of no more than 7 participants on an engaging journey through historic neighborhoods, uncovering hidden gems and sampling 5 local specialties like conch fritters and key lime pie.
Valued at $90.19 per person, the tour offers exceptional value, with free cancellation and the option to book now and pay later.
Guests depart with exclusive recipes, dining recommendations, and special discounts, ensuring a truly memorable exploration of Key West’s unique character.
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Southernmost Key West History and Culture Small-Group Walking Tour
Immersing visitors in the captivating history and vibrant culture of Key West, the Southernmost Key West History and Culture Small-Group Walking Tour offers an enriching exploration of the island’s iconic landmarks and hidden gems.
Led by knowledgeable local guides, this 1.4-to-1.8-mile stroll showcases the vibrant architecture, significant historical sites, and compelling personal anecdotes that define Key West’s unique character.
Capped at just 10 travelers, the tour provides an intimate and personalized experience, with the use of an iPad enhancing the storytelling.
Highly recommended by past participants, the tour’s exceptional value and consistently excellent reviews make it a must-do for first-time visitors seeking to uncover the essence of this captivating Florida destination.
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Dark Corners of Key West – Walking Tour
Delving into the darker corners of Key West, the Dark Corners of Key West – Walking Tour offers an immersive exploration of the island’s haunted history and paranormal legends.
This 2-hour walking tour takes participants through the city’s eerie sites, uncovering the bizarre histories of locations like The Artist House and Dean-Lopez Funeral Home.
Visitors will hear haunting tales of St. Paul’s Church and the legend of Robert the Doll, while discovering ghostly legends at Marrero’s Mansion and Capt Tony’s Saloon.
The tour also uncovers the mysteries of Captain Watlington’s Haunted House at 322 Duval St.
With flexible booking options and a professional local guide, this tour provides a unique insight into Key West’s dark and untold stories.
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The Ghosts of Key West Walking Tour
What sets The Ghosts of Key West Walking Tour apart is its focus on the island’s rich paranormal history and haunting legends.
This evening tour takes guests on a 2-hour journey through Key West’s spookiest sites, including the historic St. Paul’s Episcopal Church and the Audubon House.
Led by knowledgeable local guides, the tour delves into the stories of prominent figures and the dark past that has left its mark on these locations.
With a maximum group size of 30, guests can engage directly with the guide and learn about the eerie hauntings that are said to linger in Key West.
The tour’s 4.5-star rating and Badge of Excellence designation suggest it’s a must-do for those seeking a unique, chilling experience in the Southernmost City.
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Old Town Key West Literary Walking Tour
While the Ghosts of Key West Walking Tour offers a chilling exploration of the island’s paranormal history, the Old Town Key West Literary Walking Tour provides a captivating journey through the homes and haunts of renowned writers.
Inspired by David A. Kaufelt’s original tour, this 90-minute, one-mile walk takes participants to the residences and favorite spots of literary icons like Shel Silverstein, Tennessee Williams, and Robert Frost.
Led by knowledgeable guides, the tour includes insightful commentary and readings, offering both literary enthusiasts and newcomers a unique perspective on Key West’s rich cultural heritage.
With a maximum group size of 12 and glowing reviews, this tour is an excellent way to take in the island’s literary legacy.
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Key West Haunted Pub Crawl Walking Tour
The Key West Haunted Pub Crawl Walking Tour takes participants on a spooky and captivating journey through the island’s historic haunted pubs and taverns.
Rated 4.5 stars based on 65 reviews, the 2-hour tour explores eerie tales and ghost stories, visiting establishments like Wine-O Bar and Lounge, Capt. Tony’s Saloon, and Shots and Giggles.
Led by knowledgeable guides, the tour provides an opportunity to learn about the haunted reputations of each pub.
While some guests report issues like not entering actual bars, the overall sentiment reflects a mix of enjoyment and disappointment, with notable experiences shared about the history and ghost stories of Key West.
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PRIVATE Key West Haunted History Walking Tour
This captivating Private Key West Haunted History Walking Tour takes visitors on an exclusive journey through the island’s spookiest haunts.
Led by knowledgeable guides, the 5-star rated tour promises an immersive experience, visiting at least five haunted mansions and two haunted bars.
Guests will hear thrilling tales of Key West’s chilling past, set against a backdrop of personalized attention and a fun, engaging atmosphere.
The tour’s flexibility, with free cancellation and unlimited rescheduling, ensures a hassle-free experience.
Accessible to all, with service animals allowed and wheelchair access, this private tour offers an unforgettable glimpse into the darker side of this historic Florida destination.
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Frequently Asked Questions
Are There Discounts Available for Group Bookings?
Many tour companies offer discounts for group bookings. Customers should inquire about group rates when making reservations, as they can often save a significant amount per person by booking as a group rather than individually.
Can the Tours Accommodate Dietary Restrictions?
Many walking tour companies accommodate dietary restrictions, offering vegetarian, vegan, and gluten-free options. Guests should inquire about specific dietary needs when booking to ensure the tour can provide appropriate accommodations.
What Is the Cancellation Policy for the Walking Tours?
The cancellation policy typically allows for full refunds if cancelled 24-48 hours in advance, depending on the tour operator. Some may offer a partial refund for shorter notice cancellations. Customers should check the specific policy when booking their walking tour.
Are the Tours Wheelchair Accessible?
The tours are wheelchair accessible, with guides who can accommodate guests with mobility challenges. However, it’s best to check with the tour operator ahead of time to ensure the specific route can accommodate a wheelchair.
How Do I Book a Private or Customized Walking Tour?
To book a private or customized walking tour, you’ll need to contact the tour company directly. Many offer this option, which allows you to tailor the experience to your interests and needs. Inquire about availability, pricing, and any accessibility requirements.
Recap
Key West offers a diverse array of walking tours that cater to various interests, from food and culture to the paranormal and literary history. These tours provide visitors with an immersive experience, allowing them to explore the island’s rich heritage and unique charm. Whether you’re interested in the culinary delights, the dark side of the city, or the haunting tales, Key West’s walking tours promise an engaging and memorable adventure.