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, ship... More

Uncover the secrets of Key West through a thrilling pirate-themed adventure! Step into the shoes of a clever detective on a sun-soaked island full of hidden clues, local legends, and centuries-old mysteries. Follow a trail of ri... More

See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour. • Find out how the town nearly went bankrupt before reinventing itself as ‘The Conch Republic�... More

Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience and discovery, not just monuments and museums. You want to understand what’s behind the ... More

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. This is private tour is customizable, meaning you can request to adjust the me... More

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team... More

You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street). You will then be taken to several of Ernest Hemingway's haunts around Old Town ... More

Where is the Best Key Lime Pie? YOU decide! 3 Pie "Samples" (1/4-1/2 slices) & a Key Lime Inspired Cocktail! Experience the allure of the finest Key Lime Pie in Key West as you embark on a flavorful stroll along the historic wate... More

Go beyond all of the Bars and drunk people to learn the “WHY” on how Key West became the home to many counter culture icons! Papa Hemingway, Jimmy Buffett, Tennessee Williams and more! This is Key West’s ONLY guided Art Hist... More

Join us every weekend for the Old Town Literary Walking Tour, a stroll through downtown Key West, illuminating stories of writers that have called our island home. Inspired by David A. Kaufelt’s original literary walking tour, ... More

Walk through Old Town Key West with a long-time local, hear the haunted history of Key West, her beautiful historic mansions, and visit a haunted bar or two. This is private tour is customizable, meaning you can request to adjus... More

We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West! Our seasoned local guide will dive into the history of Old Fisherman’s Wharf & how it has transformed into Yacht Harbor! ... More

On our Secret Food Tour: Key West Old Town, we'll walk far from the tourist traps of Duval to show you the real city and its best food. You'll gain insight into how the diverse cultural influences of Key West have shaped the islan... More

Discover the sweeter side of paradise on the Key West Sweets Tour! This fun and flavorful walking tour takes you through the heart of Old Town, along the harborfront and seaport, with stops at some of the best local spots for deli... More

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s Episcopal Church, where we will share stories of its haunted past and the intriguing legend o... More

This self-guided audio tour takes you through the Key West Cemetery, a unique graveyard filled with characters that shaped the island's bohemian past. Join Frank Everhart, a nearly 30-year Key West resident, on a walking tour wher... More

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... More

You may have heard the island of Key West called many different things – America’s Caribbean Island, Margaritaville or The Conch Republic. But you know what we locals call it? Paradise!! And I bet by the end of our tour you wi... More

Tours will begin at the corridor of the Southernmost District near the Key West Lighthouse and the home of the infamous author Ernest Hemingway. We will proceed through the Southernmost District and continue onto the neighborhood ... More

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering hidden gems and local lore along the way . Explor... More