Top Key West Walking Tours

Discover Key West through its most iconic dessert on a small-group walking tour of the Historic Seaport. Sample different styles of key lime pie and a cocktail while a guide shares local history and context. Combining tastings with storytelling, this experience offers a structured, engaging, and delicious way to explore Key West—perfect for first-time visitors and avid foodies alike.

Explore Key West through the eyes of a local on a craft cocktail tour that stops at six off–the–beaten–path establishments for drinks and food tastings, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.

Explore the best that Key West has to offer on this narrated, hop-on, hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Enjoy free admission to the Sails to Rails Museum for extra sightseeing fun.

Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.

Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the docks into some of the most colorful neighborhoods in Key West, pausing to sample locally caught pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere.

Explore beautiful coastlines, wild history, and fascinating wildlife with this self-guided walking tour of Key West. Get to know famed author Ernest Hemingway and the island’s influence on his work. Hear stories of pirates, shipwrecks, and disasters and marvel at lush tropical gardens and coastline. Then stroll along Duval Street, the bustling heart of Key West, and savor the rich culture of this one-of-a-kind island. After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Explore the streets of Key West on this guided small-group walking tour. As you wander through Old Town, discover the history and culture of the island, which includes tales of shipwrecks, cigar manufacturing, and treasure hunting. Stop at popular attractions such as the Ernest Hemingway Home and Museum, the Southernmost Point, and Audubon House & Tropical Gardens.

Discover the spooky side to one of the country's most haunted cities on a 90-minute walking tour. Listen to hair-raising local legends as you follow your guide down the hidden alley's of Key West. See where Robert the Doll lived, learn about Count Von Cosel, and keep your eyes peeled for the ghost at La Concha. Learn how to attract spirit activity with dowsing rods and how to capture it with your camera.

Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.

Pedal through the charming streets of Old Town Key West on a guided bike tour, perfect for first-timers exploring the island. Along the way, you’ll uncover its rich history and stop at iconic spots like Mallory Square, Mile Marker Zero, and the Southernmost Point Buoy. With morning and afternoon tour options, it’s easy to soak in panoramic ocean views and experience Key West at your own pace.

Get a different perspective of Key West and visit some lively local spots at the same time during this haunted pub crawl tour. Take a journey through the streets of Key West as your guide regales you with scary stories. From eerie tales of possessed dolls to creepy encounters with the macabre, enjoy the entertainment as you visit various landmarks.

Jimmy Buffett has left his mark on Key West since he arrived 50 years ago. If you have a passion for all things Buffett and Margaritaville, this walking tour is the best way to find the locations around Old Key West that inspired his songs. Your guide will also take you to the location of his first gig, some of his favorite watering holes, bars he played in and his recording studio.

From local shrimp to the perfect Key lime pie, Key West dining is a food-lover’s dream, but finding authentic flavors can be a challenge in a town packed with touristy restaurants. Discover the very best bites on a gourmet tour that samples a little bit of everything, exploring Key West’s charming neighborhoods, colorful characters, and history along the way.

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

Follow in the footsteps of Ernest Hemingway during a walking tour that focuses on food, culture, and history. Exploring Key West on foot means that you'll get a more intimate glimpse into the historic area, which is characterized by its charming bars and plethora of museums. Plus, you'll receive personalized attention as you explore in a small group limited to only 15 other travelers.

Key West is rich in spooky history but you need a local's insight to fill you in. This walking tour is focused on the island city's hauntings and ghost tales. As you visit notable spots such as St. Paul's Episcopal Church and the Audubon House and Tropical Gardens, your guide will shed light on prominent figures and the dark history of Key West.

Key West's most mind-blowing sky watch! Search for UFOs with your military-grade night vision scope as we blow your mind with tales of UFOs, UAPs, alien encounters, and the hidden history of UFOs in Key West. Small groups, local guides, little-known history, and oceanfront viewing sites make this a unique, unusual, unforgettable experience. Your $5000 night vision scope will change how you see the night sky forever. This experience is dependent on suitable viewing conditions. If we cancel you will have the option to reschedule or be refunded.

Slip into Jimmy Buffett and Hemingway’s sandals and see iconic island sights on this self-guided audio tour. Key West’s quirky island lifestyle has attracted larger-than-life characters, including author Ernest Hemingway, singer Jimmy Buffet, and treasure hunter Mel Fisher. On this walking tour, you’ll hear about the legendary people the island has attracted over the years and see where they made history. Your guide is none other than Frank Everhart, the Schooner Wharf Bar’s very own comedic magician, whose tales are as captivating as the history they’re woven from. Frank, with his intimate knowledge and personal anecdotes, will show you the museums, bars and often-overlooked corners where treasure hunters, eccentrics, and unforgettable locals left their mark. You’ll even see Jimmy Buffet’s first home and his Key West recording studio, Shrimpboat Sound Studio.

Journey through Key West's history on this self-guided adventure featuring swashbuckling pirate legends and maritime mysteries. Your smartphone transforms a regular walk into an epic quest, with historical puzzles, fascinating stories, and clever challenges at every stop. Each location brings history to life — from ancient landmarks to hidden historical details you'd walk right past without the app. Solve challenges to unlock the next chapter of Key West's story. This 1–2 hour private adventure runs 24/7. No guide needed — just your smartphone and a sense of curiosity. Available in 5+ languages.

Discover Key West’s best live music with a local guide. Visit 4 music venues in two hours. The Ticket includes, drink discounts, digital guide for upcoming events, digital download of local artists music, and historical overviews of the venues and artists who have left their mark on the island. Learn from a local about the diverse music scene and creative island life that continues to inspire so many.

Discover some of Key West’s deepest, darkest secrets on a ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of what is said to be one of the most haunted cities in the US. Travel down the narrow, dark streets of the Old Town at night. The wooden houses still bear the secrets of their former inhabitants. This tour is narrated by an actor playing a gravedigger.

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic buildings with unique histories, uncovering tales of colorful figures who shaped the island, from renowned writers to influential locals. As we stroll through beautifully preserved architecture, you’ll gain insights into the significance of each site, connecting with the spirit of Key West. This tour offers a chance to experience the essence of the island through its rich stories, creating an unforgettable adventure filled with intrigue and nostalgia. Don’t miss out on this magical journey!

True crime in Key West? Bold, bizarre, and unforgettable, this new innovative tour walks you into the island’s real-life scandals — smuggling, gambling, murder, and shocking history exposed where it happened. More thrilling than a ghost tour and more revealing than a history tour, Key West’s underworld comes alive, Key West-style. Be the next eyewitness. We're bringing crime to the streets!