Key West Historical & Heritage Tours

Discover the locals, on foot, at eye level. Walk around Key West and explore its culture and natural history with an experienced guide. Begin your tour at Kino Sandals before heading toward the Southernmost Point of the continental United States. Meet locals, experience popular landmarks, and get a unique...Read more

Witness the past of Key West with a limited-size guided walking journey! This excursion will give you an understanding of the island's first occupations such as salvaging and cigar manufacturing, as well as other local history. You'll be led by one of our knowledgeable guides through picturesque streets in the Old Town, giving you a unique...Read more

Embark on a journey with us for a remarkable and unforgettable Key West experience! Your own local guide will show you the islands' top sights. Sail through Old Town, explore famous landmarks, and listen to tales about the interesting people who have lived in Key West. Our leisurely 2.5 hour ride is great for both you and our stunning...Read more

Tripadvisor ranked our tour as the top 10 history tours in North America for 2022. Our award-winning guides will take you on a memorable 2.25 hour stroll through the captivating Old Town district of Key West, home to many historic homes and iconic architectural edifices that have long been part of the culture and folklore of this remarkable...Read more

Every weekend, come take part in the Old Town Literary Walking Tour - a leisurely stroll through downtown Key West that shines a light on the writers who have called our island their home. Drawing inspiration from David A. Kaufelt's original literary walking tour, this new experience will show you the former residences and favorite spots...Read more

The Ghosts of Key West Tour is a great pick for families and those interested in the region's history, hauntings, and legends. On this tour you’ll explore prominent figures from the past; as well as Robert the Doll, The La Concha Hotel, haunted mansions, hotels, and...Read more

Once you dock in Key West, set out on your own Conch Tour Train tour for a unique way to explore the city. Established in 1958, this fun and informative shore excursion will give you a glimpse into the legends and lore of the charming tropical paradise that is Key West. Learn all about Henry Flagler's railroad, which arrived in 1912 and...Read more

< Experience the renowned Conch Tour Train of Key West! As one of Florida’s most beloved attractions, this train has been pleasing visitors to ‘The Island City’ for years. Discover the story of the train, a tribute to Henry Flagler's amazing feat when he constructed the railroad in 1912, and take a relaxing ride around this picturesque...Read more

Relax on your spacious and comfortable tiki bike as you take in the sights of Old Town and Historic District while your private guide/driver narrates the rich history, culture, and folklore of Key West! Enjoy the fascinating architecture and historic sites of our beautiful island. As a sweet bonus, each guest will receive a slice of Kermit's...Read more

Join our acclaimed guides for an enjoyable, entertaining, and educational 2.5 hour stroll through the legendary streets of Old Town Key West. Our objective is for you to have a remarkable experience as we bring to life the vibrant and intriguing history, records, points of interest, flora/fauna, and culture that make Old Town Key West...Read more

Transform your phone or tablet into a personal tour guide! Download this location-sensitive audio/visual tour, then explore.

PLEASE NOTE ELECTRIC CAR, SCOOTER OR BIKE HIRE IS NOT INCLUDED.

Rent from one of the vendors suggested at the start of the tour, then discover at your own pace. The speed limit won't exceed 35 mph...Read more

Transform your phone or tablet into a localized audio/multimedia guide and explore historic photos, recordings, and videos plus menus of nearby happy hour spots and connected websites. In just 35 minutes, you can chill at a tiki bar with a beautiful waterfall then explore the hidden boardwalk with impressive ocean views. Discover the...Read more

Our award-winning guides will take you on an exciting, educational, and entertaining 2.5 hour walk through the streets of Old Town Key West and share its incredible history, legends, points of interest, fauna/flora, and culture that make it famous around the world. Our goal is for you to have a memorable experience!

We...Read more

Journey with our award-winning guides on a captivating, entertaining, and informative walk through the marvelous Old Town neighborhoods of Key West. Explore the history and marvel at the distinguished homes and unique architectural monuments that have played an important role in shaping the culture and legends of this remarkable island...Read more

Comfortably stroll through Old Town Key West with a local guide and discover the unique places you can visit during your vacation. This private tour is only for your group, no strangers included! It doesn't matter if it's a wedding party, couple, family & friends, bachelor/bachelorette party, birthday celebration, reunion or corporate event -...Read more

Depart the island of Key West and experience a whole day of sightseeing along the renowned Overseas Highway! You'll go up to Marathon in the middle of the keys, making stops on your journey to explore both the natural beauty and man-made marvels of the Florida Keys. Such halts will enclose the Florida Keys Aquarium Encounters, Bahia Honda...Read more

Explore Key West with a seasoned local and delve into the spooky history of this beautiful town, including its captivating historic properties and possibly some haunted pubs.

This is specifically for you and your group - we won't mix you up with others. It's ideal for weddings, couples, family & friends, bachelorette parties,...Read more

Transform your phone or tablet into an area-informed sound and multimedia visit! Nearby information, old photographs, and connections to sites and eatery menus are readily available.

In just sixty minutes of simple strolling, find out about the history, culture, and cooking of Key West without a single misstep. Visit the most...Read more