Key West’s best walking tours combine local food, history, and culture in compact, information-packed experiences. I especially recommend the food and culture walks for their practical mix of neighborhood exploration and authentic Keys cuisine.
The intimate small-group historic home tours give the best access to hidden courtyards and architectural gems, while evening ghost tours add a fun dose of spooky lore to historical facts.
Back-street routes help avoid tourist crowds and reveal the real Key West. These are our favorite walking tours worth your time and money:
Good To Know
- Key West offers a range of popular walking tours that provide immersive experiences exploring the island’s vibrant culture, cuisine, and rich history.
- Food and cultural walking tours showcase the diverse flavors and architectural wonders of Key West’s historic Old Town and seaport area.
- Historic walking tours explore the captivating stories and architectural gems that have shaped the island’s unique character over the centuries.
- Haunted history tours offer a spooky and captivating journey through Key West’s supernatural past, visiting iconic haunted sites and landmarks.
- Self-guided walking tours allow visitors to uncover the island’s grizzly histories and tales at their own pace using mobile apps and audio guides.
Key West Southernmost Food and Cultural Walking Tour
Set out on a delectable journey through Key West’s vibrant culture and cuisine on the Southernmost Food & Cultural Walking Tour. With over 1,299 reviews and a 98% recommendation rate, this 1.2-mile walking tour promises an exceptional experience.
You’ll savor 4 food tastings and 1 alcoholic beverage, totaling a hearty lunch, as you explore historic Old Town. Guided by a friendly local, you’ll uncover the island’s architecture, history, and daily life.
Visiting an island backyard bistro, a family-owned Cuban restaurant, a café known for its coffee and key lime pie, and an old speakeasy, you’ll indulge in the flavors that make Key West unique. Don’t forget to bring comfortable shoes and any dietary restrictions.
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Key West Historic Seaport Food Tasting and Cultural Walking Tour
Enjoy the vibrant flavors and rich history of Key West’s Historic Seaport on this engaging food tasting and cultural walking tour. You’ll visit 5 unique locations, savoring locally-caught seafood and other tasty options. Led by a knowledgeable local guide, you’ll explore the town, learning about its culture and heritage.
The tour is suitable for most dietary needs, though not recommended for vegetarians/vegans. With a maximum of 12 travelers, you’ll enjoy an intimate experience. Wear comfortable shoes and bring sun protection, as the tour runs rain or shine.
Discover the essence of Key West’s culinary scene and uncover its fascinating past on this delightful excursion.
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Key West Historic Homes and Island History – Small Group Walking Tour
Dive into the rich history and architectural wonders of Key West on this captivating small-group walking tour. Led by a professional, friendly, and highly trained local guide, you’ll explore historic buildings, including the Casa Antigua and Curry Mansion Inn, as well as Truman Annex Park.
With a maximum of 10 people, you’ll enjoy a personalized experience and gain in-depth insights into the island’s past. The tour starts at the Mel Fisher Maritime Museum and ends at the Captain John Bartlum House. Suitable for travelers with moderate fitness, this tour provides rain ponchos and umbrellas if needed.
With a 99% recommendation rate from 366 reviews, this is a must-do activity for anyone interested in Key West’s history and culture.
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Highlights and Stories of Key West – Small Group Walking Tour
Step into the vibrant heart of Key West on this captivating small-group walking tour. Led by a professional, friendly, and highly-trained local guide, you’ll discover the island’s rich history and cultural gems.
Marvel at the architectural charm of historic homes, and savor insider tips on the best places to dine. Rain ponchos, bottled water, and umbrellas are provided if needed, ensuring your comfort throughout the journey.
The tour starts at the Mel Fisher Maritime Museum and ends at the iconic Mansion On The Sea, covering a maximum group size of 10 travelers. With free cancellation and wheelchair accessibility, this tour is perfect for all ability levels.
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Key West Historic District Small-Group Walking Tour
Amid the vibrant charm of Key West’s Historic District, you’ll embark on a small-group walking tour that unveils the island’s captivating history and cultural gems. Led by a knowledgeable local guide, you’ll stroll through the picturesque streets, learning about the lore and legends that have shaped this unique destination.
Along the way, you’ll see famous landmarks and discover hidden gems that you might’ve missed on your own. With a bike rack and ponchos provided if needed, you’ll cover 1.4 to 1.8 miles at a moderate pace, ensuring a comfortable and immersive experience. With a 99% traveler recommendation, this tour promises an unforgettable exploration of Key West’s rich heritage.
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Key West Walking Food Tour With Secret Food Tours
This delightful Key West Walking Food Tour with Secret Food Tours invites you to explore the island’s vibrant neighborhoods, uncovering its captivating history and diverse culinary offerings. You’ll savor a range of flavors, from authentic Cuban cuisine to freshly baked cakes and chocolate-dipped key lime pie.
Along the way, you’ll discover eateries off the tourist trail, gaining a glimpse into the local way of life. With a maximum of 12 travelers, the tour provides an intimate and personalized experience. Conveniently starting and ending in central Key West, this highly recommended tour has earned a Badge of Excellence from Secret Food Tours, thanks to its 96% traveler recommendation rate and 190 positive reviews.
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The Ghosts of Key West Walking Tour
Set out on a captivating journey through Key West’s haunted past with The Ghosts of Key West Walking Tour. Led by a local and professional guide, this 1.5-hour tour takes you to the most notorious haunted sites in the city. With 114 glowing reviews and a Badge of Excellence, this tour is a must-do for anyone seeking a spine-tingling experience.
The tour starts at 8 PM, meeting outside St. Paul’s Episcopal Church, and covers all taxes and fees. Wheelchair and stroller accessible, the tour has a maximum group size of 30 travelers. However, it’s not recommended for those with back problems or pregnant travelers, as a moderate fitness level is required.
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Old Key West: Small-Group Jimmy Buffet Walking Tour
Enjoy the vibrant legacy of Jimmy Buffett on the Old Key West: Small-Group Jimmy Buffet Walking Tour. This 1.5-hour experience boasts 158 glowing reviews and a 92% recommendation rate.
Explore the Key West locations that inspired the legendary musician’s life and career. Visit spots where Buffett performed his first gigs, discover his recording studio, and uncover the restaurants and hangouts he frequented. Along the way, you’ll savor a slice of Key Lime Pie and refreshing beverages.
With a knowledgeable guide leading the way, you’ll explore Buffett’s enduring impact on the island’s culture. Maximum group size is 15, ensuring an intimate and engaging tour. Whether you’re a Parrothead or simply seeking a unique cultural experience, this tour offers an immersive glimpse into Key West’s iconic musical legacy.
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Hemingway Food and Walking Tour
Explore the vibrant culinary and literary legacy of Ernest Hemingway on the Hemingway Food and Walking Tour. This highly-rated tour takes you through Key West’s historic sights, including the Hemingway Home and Museum and Capt Tony’s Saloon. Sample local favorites like chicken street tacos and conch fritters, and indulge in a classic Key lime pie.
With a maximum of 15 travelers, you’ll enjoy an intimate experience led by knowledgeable guides. At just $94.35 per person, this tour offers excellent value and a Badge of Excellence. Confirm your booking in advance, as spots are limited. Whether you’re a Hemingway fan or simply seeking a delicious culinary adventure, this tour isn’t to be missed.
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Key West Haunted Pub Crawl Walking Tour
While you explore Key West’s vibrant nightlife, uncover the island’s spooky supernatural history on the Key West Haunted Pub Crawl Walking Tour. This 2-hour tour, rated with a Badge of Excellence by Ghost City Tours, takes you to several haunted pubs, where you’ll enjoy alcoholic beverages as you learn about the paranormal activity.
The tour departs from the Key West Chamber of Commerce and ends at the famous Capt Tony’s Saloon. With a maximum of 20 travelers, this tour isn’t wheelchair accessible and not recommended for pregnant guests. For $29.99 per person, you can experience this unique ghost tour with a 24-hour free cancellation policy.
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PRIVATE Key West Haunted History Walking Tour
Take your exploration of Key West’s haunted history to the next level with the Private Key West Haunted History Walking Tour. This personalized experience takes you to at least 5 haunted mansions and 2 haunted bars, where your knowledgeable guide shares tales of the city’s spooky past.
Exclusively for your group, you’ll visit iconic locations like the Bearded Lady Key West and Capt Tony’s Saloon, enjoying the paranormal. With a 100% recommendation from previous travelers, this 7:30 PM tour promises an unforgettable journey through Key West’s dark and haunted history.
Don’t miss this opportunity to uncover the supernatural side of this captivating island destination.
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Private Highlights and Stories of Key West Walking Tour
Explore the captivating history and landmarks of Key West’s Old Town on this private walking tour. Led by a local resident, you’ll explore the colorful personalities and stories that shaped this unique island city.
Visit the most important landmarks, hearing insider insights and local tales from your guide. Whether you’re a first-time visitor or a seasoned Key West enthusiast, this exclusive tour offers a personalized experience, complete with recommendations on the best places to dine. With rain protection provided, you’ll discover the charm and character of Old Town, rain or shine. This private tour is perfect for those seeking an intimate, informative exploration of Key West.
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Private Key West Historic Homes and Island History Walking Tour
Set out on a captivating journey through Key West’s historic homes and island history on this private walking tour. Led by a professional, friendly, and highly trained local guide, you’ll explore the city’s unique architecture and uncover its fascinating past.
The tour provides rain ponchos and umbrellas if the weather is inclement, ensuring your comfort. While alcoholic beverages and bottled water aren’t included, you can purchase them along the way. The meeting point is the Sidewalk at 200 Greene Street, and the tour concludes at the Captain John Bartlum House.
This tour isn’t recommended for travelers with back problems or serious medical conditions, and a moderate physical fitness level is required.
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Explore Key West’s haunted past with the self-guided ghost walking tour on the WalknTours app. This smartphone-guided tour lets you uncover the island’s grizzly histories at your own pace.
Visit allegedly haunted sites like Captain Tony’s Saloon, the Hard Rock Cafe, and Casa Antigua. Hear the chilling tales of these locations and relive the experience again and again. With 8 reviews, this private tour is perfect for visitors seeking an intimate ghost exploration.
The tour starts and ends at iconic Key West spots, allowing you to seamlessly incorporate it into your day. Accessible and available year-round, this self-guided ghost walk is a must for anyone wanting to experience Key West’s haunted side.
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Florida Key West Self-Guided Walking Audio Tour
Tackle the history and sights of Key West at your own pace with the self-guided Florida Key West Walking Audio Tour. Enjoy engaging storytelling, voiced by professionals, as you explore the island’s unique tales and history.
Conveniently access offline maps, location-based audio, and extra content to dive deeper into each stop. Customize your experience – start anytime, take breaks, and revisit favorites. With comprehensive route planning and no need for cellular or WiFi, you’ll enjoy a hands-free, flexible tour suitable for couples or small groups.
Simply download the app, enter your password, and begin your adventure from the starting point. Discover Key West on your terms with this versatile walking audio tour.
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Key West: Hemingway’s Life and Local Food Walking Tour
Step into the captivating world of Ernest Hemingway on this comprehensive walking tour in Key West. For just $99 per person, you’ll embark on a 2-hour journey, tracing the steps of the legendary author.
Explore the Hemingway House, visit the boxing match venue, and discover the location of his beloved boat, “Pilar.” Indulge in local delicacies like street tacos, conch fritters, and key lime pie. With a knowledgeable guide, you’ll uncover incredible facts about Hemingway’s life and times.
Complimentary entry to the Hemingway House and Museum is included, along with three delectable food tastings. Reviews praise the tour guide, Caleb, for making the experience both memorable and enriching. Don’t miss this opportunity to learn about Hemingway’s iconic legacy.
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Key West: Southernmost Food and Cultural Walking Tour
Enjoy the vibrant cultural tapestry of Key West on this 3-hour small group walking tour. Discover Cuban and Caribbean influences that have shaped the island’s food and heritage. You’ll visit 5 local eateries, savoring iconic dishes and learning unique facts from a knowledgeable guide.
Explore historic neighborhoods, uncovering hidden gems along the way. Complement your culinary journey with an e-guide booklet, signature recipes, and shopping coupons. Dress comfortably, bring sun protection, and be prepared for any weather. This tour operates rain or shine, ensuring you experience the true essence of Key West’s Southernmost food and cultural wonders.
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Key West: Food Tasting and Cultural Walking Tour
Set out on a delightful culinary and cultural exploration of Key West’s historic seaport on this 3-hour guided walking tour. You’ll discover hidden gems at 6 tasting locations, savoring seafood and island-inspired drinks.
Along the way, dive into the seaport’s riveting history and charming architecture through an entertaining local guide. Learn about the significance of conch, a local delicacy. Capture excellent photos of flora, artist murals, and landmarks.
This small-group experience provides a personalized journey, complete with an e-guide, recipe collection, and exclusive privileges at partner restaurants. With 1.5 miles of ADA-accessible walking, this tour offers a hearty lunch and an eclectic taste of Key West’s best.
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Key West: Jimmy Buffet Walking Tour With Key Lime Pie
If you’re a fan of Jimmy Buffett and his laid-back island vibes, you won’t want to miss the Jimmy Buffett Walking Tour in Key West. This 1.5-hour guided tour takes you to the locations that inspired Buffett’s songs, including his first gig and recording studio.
You’ll also visit famous watering holes like Capt. Tony’s Saloon and Margaritaville resort while learning about Buffett’s life and times in the area. The tour includes a slice of Key Lime pie, water, and an alcoholic beverage for adults. It operates rain or shine and is suitable for most fitness levels, but not for those with mobility impairments.
Don’t miss this chance to learn about the world of the “Cheeseburger in Paradise” singer.
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Key West: History and Culture Southernmost Walking Tour
Explore Key West’s rich history and diverse culture on this engaging 1.5-hour walking tour through the island’s southernmost area. Led by a knowledgeable local guide, you’ll learn about Key West’s fascinating past, including its shipwrecking industry, sponge harvesting, and cigar manufacturing.
Visit popular sites and discover how the island was first discovered. Along the way, you’ll walk 1.4 to 1.8 miles through the warm streets, taking in the sights and sounds of this unique destination. Though not recommended for those with limited mobility, the tour operates rain or shine, providing maps to ensure you don’t miss a thing.
Enjoy Key West’s vibrant history and culture on this informative southernmost walking tour.
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Frequently Asked Questions
What Is the Dress Code for the Walking Tours?
As for the dress code, it’s best to wear comfortable, casual attire. Opt for lightweight, breathable fabrics and closed-toe shoes for the walking tour. You’ll be on your feet for a while, so prioritize comfort over style.
Are the Walking Tours Suitable for Children?
The walking tours are generally suitable for children, but it’s best to check with the tour operator beforehand. They may have age or size restrictions, and the pace and content may not be appropriate for younger kids.
Can We Bring Our Own Food and Drinks on the Tours?
You’re generally welcome to bring your own food and drinks on walking tours in Key West. However, it’s best to check with the tour company beforehand to ensure their specific policies. Enjoying snacks and refreshments can enhance your walking tour experience.
How Much Walking Is Involved in Each Tour?
The amount of walking varies depending on the tour, but you can expect to cover several miles over the course of the experience. Be prepared with comfortable shoes and a willingness to explore on foot.
Are the Tours Wheelchair/Stroller Accessible?
The tours vary in accessibility, so it’s best to check with the tour operators. Some may be wheelchair and stroller-friendly, while others may have more challenging terrain. Be sure to inquire about the specific accommodations available for your needs.
The Sum Up
Discover the vibrant culture, delectable cuisine, and rich history of Key West on these engaging walking tours. Whether you’re interested in food, architecture, or general sightseeing, there’s a tour to suit your interests. Enjoy the unique charm of this island paradise and create lasting memories. Don’t miss the opportunity to explore Key West on foot and uncover its hidden gems.