The 16 Best Walking Tours in Key West
Key West’s compact size makes it perfect for exploring on foot. Narrow streets, pastel-colored buildings, and a lively mix of history, art, and food create a walking-friendly atmosphere that invites discovery at every turn. Unlike bus tours or boat trips, walking tours let you experience the details—the quirky facades, local stories, and flavors that make Key West unique. Whether you’re into ghost stories, Hemingway’s haunts, or sampling fresh seafood, there’s a tour that will help you see the island from a fresh perspective.
In this guide, we’ll walk through the top 16 walking tours in Key West. From culinary adventures to spooky ghost hunts, each offers something special. We’ll help you choose the one that best fits your interests, budget, and schedule—so you can make the most of your time on this lively island.
1. Key West Historic Seaport Food & Walking Tour
This tour is a fantastic way to combine local cuisine with history. Over approximately three hours, you’ll stroll from the docks into colorful neighborhoods, sampling seafood like pink shrimp and spiny lobster, or other local specialties. Your guide shares stories about Key West’s maritime past and culture while you enjoy tastings at spots like Garbo’s Grill and Eaton Street Seafood Market. One highlight is tasting fresh Key West Pink Shrimp paired with white wine, and ending with the famous key lime pie.
What makes this tour stand out is the balance of food, culture, and history in a small group setting. Reviewers love the personal attention and “interesting facts” from guides like Sharon and Coraly. At just over $93, it offers excellent value for those eager to combine culinary discovery with storytelling.
Bottom Line: Perfect for foodies who want an active, tasty introduction to Key West’s maritime history and local flavors.
2. The Ghosts of Key West Walking Tour
For those intrigued by the supernatural side of Key West, this 1.5-hour ghost walk is an excellent choice. It explores haunted sites like St. Paul’s Episcopal Church and the Artist House Bed and Breakfast, revealing spooky tales of restless spirits and eerie legends. Your guide tells stories of Key West’s darker history, with mention of the unmarked graves and ghostly happenings that persist at places like the cemetery and old buildings.
This tour provides a different lens on the island’s past, making it ideal for history lovers with a taste for the macabre. With a budget-friendly price of just under $25, it’s a fun, quick way to add some chills to your trip. The reviews note how fun and knowledgeable the guides like Bianca are, with a love of local lore.
Bottom Line: Great for those interested in ghost stories and haunted history, especially if you’re curious about the mysterious side of Key West.
3. Hemingway Food and Walking Tour
Following the footsteps of Ernest Hemingway, this two-hour tour combines literature, history, and local cuisine. Starting outside the Hemingway House, you’ll visit sites like Sloppy Joes, the boat Pilar, and Hemingway’s first apartment. The tour includes a tasty lunch and Key Lime Pie, along with visits to Hemingway-related landmarks like the bookstore and nearby bars.
This tour appeals to fans of Hemingway or those interested in the cultural atmosphere of Old Town. The small-group setting is perfect for personalized stories, and the inclusion of food and drinks makes it a well-rounded experience for around $99. Reviewers praise guides like Caleb for their rich knowledge and witty storytelling.
Bottom Line: Ideal for literary enthusiasts and history buffs wanting an immersive, edible experience tied to Hemingway’s Key West life.
4. Key Lime Pie Walking Tour of Key West Historic Seaport
This flavorful tour is a sweet way to explore the historic waterfront in Old Town. Over approximately 90 minutes, you’ll visit three local favorites to sample Key Lime Pie and enjoy a Key Lime Cocktail of the Day. Along the way, your guide shares stories about Key West’s maritime history and how the famous dessert became a local signature.
What makes this tour special is its focus on food and history combined, along with the chance to taste some of the best Key Lime Pie in town. With all reviews rating it a perfect 5 stars, it’s clear that the tour delivers both deliciousness and insight. At just over $63, it offers sweet value for a fun, indulgent experience.
Bottom Line: Perfect for sweet tooths and history lovers eager to combine culinary delights with waterfront views.
5. PRIVATE Welcome to Key West Walking Tour
For those wanting all the highlights without the crowds, this private tour is a flexible and personalized option. For 1.5 to 3 hours, your small group can customize the itinerary—visiting everything from the Southernmost Point to Mallory Square, plus hidden spots like the butterfly house. Your guide shares tailored stories about Key West’s culture, attractions, and history.
This tour suits travelers seeking a customized experience away from large groups. The $137.50 price includes undivided attention and the chance to focus on your specific interests. Reviewers say it’s a “great way to see the city” with guides like Whiskey Rick providing both fun and informative commentary.
Bottom Line: Best for privacy, customization, or those with specific sites in mind.
6. Key West Haunted Pub Crawl Walking Tour
Combine ghost stories with drinks on this two-hour haunted pub crawl. Starting at Shots & Giggles, you’ll visit historic pubs like Capt. Tony’s and learn about their haunted reputations. Your guide shares chilling tales of demonic dolls and restless spirits, with a focus on the darker side of Key West’s nightlife.
If you enjoy spooky stories and a lively atmosphere, this tour offers a fun blend of history and entertainment. Priced at only $35, it’s budget-friendly and highly rated for its storytelling. Reviewers mention the engaging guides and creepy stories that keep the evening lively.
Bottom Line: Great for groups who want a laid-back, spooky night out with local legends and a few drinks.
7. Key West: Secret Walking Food Tour
This three-hour walk takes you off the beaten path in the Old Town district, focusing on authentic local eateries and cuisine. You’ll visit spots like El Siboney and Mangoes, sampling hearty Cuban sandwiches, conch fritters, and other island staples. The guide shares insights into Key West’s food scene and architecture along the route.
The tour is suited for travelers who want a more intimate, less touristy experience of Key West’s culinary scene. The small group size and inclusion of food make it a good value at $116. Reviewers highlight the quality of food and knowledgeable guides like Kitty.
Bottom Line: Perfect for food lovers who want to experience local flavors in a relaxed setting.
8. Key West: History and Culture Southernmost Walking Tour
This 1.5-hour tour offers a compact overview of Key West’s history and culture, starting at the southernmost point of the U.S. It covers key sites and explains how the island was discovered, developed, and shaped by different industries. The guide makes history accessible and engaging, with practical tips along the way.
Rated almost 5 stars, it’s a solid choice for those wanting a quick but informative introduction. The guide’s storytelling is praised, and it’s an excellent way to orient yourself on your first day. Costing only $40, it’s a budget-friendly option for a short, informative walk.
Bottom Line: Ideal for travelers who want a quick, well-paced overview of Key West’s history and culture.
9. PRIVATE Key West Haunted History Walking Tour
This private tour focuses on the most haunted sites, including mansions and bars known for spooky legends. For around 1.5 to 2 hours, your group visits at least five haunted locations, hearing stories of paranormal activity and grisly murders. You’ll explore the eerie stories behind places like the Curry Mansion Inn and haunted bars.
It’s perfect for those who prefer personalized, intimate ghost stories with undivided attention from the guide. The $137.50 price reflects the private setup, and reviews emphasize the guide’s storytelling skills and the exclusive experience.
Bottom Line: Best for ghost enthusiasts seeking a tailored, private experience in Key West’s haunted sites.
10. Key West: Jimmy Buffett Walking Tour with Key Lime Pie
Follow in the footsteps of Jimmy Buffett in this 1.5-hour tour. You’ll visit locations where the singer-songwriter played early gigs and see his recording studio. The tour includes a slice of Key Lime Pie and a souvenir drink, making the experience both musical and culinary.
For fans of Buffett’s laid-back style, this tour hits the right notes. Caleb, the guide, is praised for his knowledge and humor, and reviewers love the chance to connect with the artist’s Key West roots. At $79, it offers good value for a mix of music, stories, and food.
Bottom Line: Great for music lovers and Buffett fans wanting a fun, relaxed walk with local flavor.
11. The Dark Side of Key West Adults Only Walking Tour
This adult-only tour explores the more sinister stories behind Key West’s buildings and figures. Over about 1.5 hours, you’ll visit haunted mansions and bars, hearing about murders, curses, and paranormal activity. The guide tells the stories behind the haunted reputation of places like the Hemingway House and Artist House.
Ideal for mature audiences interested in ghosts and grisly tales, the $35 price makes it accessible. Reviewers mention how much they learn about the darker history that lurks behind the sunny facade of Key West.
Bottom Line: Perfect for adults wanting a slightly spooky, more intense ghost tour.
12. Key West: Hemingway’s Life and Local Food Walking Tour
This two-hour tour combines literature and cuisine. Starting outside Hemingway’s home, you’ll visit places associated with his life—fishing spots, bars, and the bookstore. Along the way, you’ll sample local specialties, making it a delicious way to learn about Hemingway’s life in Key West.
Reviewers note how guides like Caleb make the stories engaging and how the food adds a tasty dimension. The $99 price covers an immersive experience that appeals to fans of Hemingway and local history alike.
Bottom Line: Well-suited for literary fans and foodies wanting a personal, edible history lesson.
13. Southernmost Food & Cultural Walking Tour by Key West Food Tours
This highly-rated (almost 1,500 reviews) tour is a three-hour culinary journey. It visits “mom and pop” eateries, sampling conch fritters, Cuban sandwiches, and Key Lime Pie. The guide offers insights into Key West’s architecture, culture, and history, making it more than just a food tour.
With a small group limit of 12 and a price of about $90, it’s a top choice for those wanting an authentic local experience. Reviewers love the variety and the engaging guide, Trish.
Bottom Line: Ideal for travelers who want a hearty, authentic meal combined with local stories and culture.
14. Key West: Haunted Pub Crawl Walking Tour
This lively two-hour pub crawl combines haunted history and local drinking spots. Visiting historic pubs such as Captain Tony’s and Shots & Giggles, your guide shares stories of ghosts and curses while you sip drinks. The focus is on history, spirits, and fun.
It’s a budget-friendly option at just $30, with reviews praising the guide’s storytelling. If you’re in the mood for a casual night out with a spooky twist, this tour delivers.
Bottom Line: Best for those looking for a relaxed, entertaining way to experience Key West’s haunted legends with a drink in hand.
15. Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration
This tour takes you through several waterfront restaurants, sampling cocktails and local bites, including oysters and Key Lime Pie. Over 2-3 hours, your guide explains Key West’s waterfront history and points out landmarks on the way to Mallory Square for sunset.
Rated 4 stars, it’s perfect for those wanting a relaxed, scenic experience with food and drinks. The tour’s steady flow of tastings and stories makes it a popular choice for sunset watchers and food fans alike.
Bottom Line: Suitable for those seeking a leisurely evening of food, drinks, and sunset views in a social setting.
16. Experience Key West Food Walking Tour
This culinary tour focuses on Caribbean flavors, exploring the island’s staples like conch fritters, Cuban sandwiches, and Key Lime Pie. Starting at Mallory Square, the 2-hour journey includes tastings at several spots, with stories about local culture and landmarks.
It’s ideal for travelers who want an authentic taste of Key West’s diverse cuisine. Priced at $113, it combines delicious food with cultural insights, making it a satisfying addition to your trip. Reviewers mention the quality of food and friendly guides.
Bottom Line: Perfect for food lovers seeking a flavorful, cultural experience in a relaxed walking tour.
How to Choose the Best Walking Tour in Key West
Picking the right walking tour depends on your interests and how you want to experience the island. If you’re a history buff or Hemingway enthusiast, consider Hemingway-focused tours or Hemingway’s life and local food. For food lovers, the Southernmost Food & Cultural Tour or Key Lime Pie Tour offer delicious bites and stories. Ghost fans should look at Ghosts of Key West and Haunted Private Tours. Budget-conscious travelers might prefer the Haunted Pub Crawl or Waterfront Cocktail Walk.
Consider your time, physical comfort, and whether you prefer private or group experiences. Book early—especially for popular tours—and check for seasonal availability or special add-ons like lunch or drinks.
Final Thoughts
Key West offers a rich variety of walking tours that let you explore its history, culture, food, and spooky legends at a comfortable pace. For a taste of local flavors, try the Historic Seaport Food & Walking Tour or the Secret Food Tour. If haunted tales intrigue you, the Ghost Tours and private ghost walks will satisfy your curiosity.
For those seeking a personalized experience, the Private Welcome Tour is a top pick. And if you want to combine music, food, and scenic views, the Jimmy Buffett Tour will hit the right note.
Whatever your interest, booking early ensures you won’t miss out on these memorable walks through one of America’s most charming islands.