Cultural Tours in Key West

We cordially invite you to join us for an extraordinary cocktail & food tasting tour of the Waterfront at Downtown Key West!
With our experienced local guide, discover the history behind Old Fisherman’s Wharf and its transformation into Yacht Harbor!
Learn all about rum running and wrecking during the days of old Key West!
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This guided walking tour will take you to the genuine spots where Hemingway lived, worked and enjoyed himself, including the venue where he watched and officiated boxing matches, his boat's mooring - The Pilar, the bookstore that sold his books, as well as his first Key West apartment -where he completed writing “A Farewell...

You will start off this 1 hour 30 minute guided tour by meeting your guide (wearing a fluorescent green shirt) at Margaritaville. Fifty years back, in 1971, Jimmy Buffett landed in Key West. This strolling trip will take you to the spots around Old Key West that motivated his melodies, where he performed his first show, some of his most loved...

You will start this 65 minute nighttime guided stroll by joining forces with your tour guide outside the entryways of Capt. Tony's Saloon (428 Greene Street). Subsequently, you will be taken to a few of Ernest Hemingway's beloved places in Old Town where he lived, worked and had some good times. You'll listen to amazing accounts of history...

This is the only ghost tour in Key West where you will meet the infamous Robert the Doll. Instead of merely stopping outside of haunted places, our tour takes place inside an old Civil War fort that USA Today named one of the 10 Most Haunted Destinations in America. Every ticket purchased supports Key West's oldest non-profit...

Sample: Indulge in a flavor of Key West during this 3-hour culinary walking tour, guided by a specialist. Visit 5 local "mom and pop" stores in historic old town, sampling typical Cuban cuisine, seafood from the area, and the iconic Key Lime Pie. Food samples are sufficient for a satisfying lunch. As you wander away from the touristy streets...

Uncover the flavors of the ocean on this guided 3-hour culinary journey around Key West. Savour maritime heritage with scrumptious seafood (or non-seafood options) cuban sandwich & key lime pie tastings. Relish classic ingredients like Key West pink shrimp, Caribbean warm-water lobster, and fresh fish. Sample white wine after walking through...

Come along with us on a delicious tour through Key West, as we visit 5 of its craftiest bars and most secret local spots. Sample five local cocktails, paired perfectly with two food tastings, to get an authentic taste of the island life! Hear the unique stories behind some iconic drinks like the Hemingway Daiquiri, and explore tiki-era...

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,...

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...

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 -...

< 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...

Climb aboard the Trolley of the Doomed and join your grave-digging guide for a night of frightful fun! Take a thrilling tour down the shadowy alleys of Old Town and listen to stories about Key West's spooky past. Your in-depth journey into the eerie history of this Southernmost City will be sure to leave you with...

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...

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...

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...