Capt Tony’s Saloon

Outdoor activities

Start by downloading the Action Tour Guide app. This serves as your personal tour guide, narrated tour, and map, all rolled into one. Once downloaded, your tour begins at the intersection of Duval Street and South Street. From there, unearth the island’s wild history and hear about the fights over its ownership, including how a Spanish naval officer sold the island to two people at the same time! As you keep walking, learn about the wreckers who once salvaged materials from destroyed ships! Then meet some of Key West’s literary legends, including larger-than-life Ernest Hemingway. Pay a visit to the Hemingway Home and Museum and learn how he left his mark on the island. Next, you’ll go back to 1886 and revisit the infamous Great Fire. Unearth the devastation and the possible arson behind the tragedy. Then get to know Henry Flagler. Hear how he fought to connect the Florida mainland with Key West by rail and learn about the challenges he overcame in the process! You’ll also get the story behind the hurricane that ultimately destroyed his railroad. On another wild note, you’ll discover the famed pirates who terrorized the area and seized riches. Meet Black Caesar and separate fact from fiction. Up next, stop by Harry Truman’s “little” White House and find out which other presidents spent time here. After that, stop at the Audubon House and Tropical Gardens. Dig into the house’s history and meet Captain John Geiger, whose family occupied it for four generations! Learn about the efforts to restore the home and how this movement helped create the Key West you see today! Your journey then takes you to Clinton Square, which features monuments that pay tribute to both Union and Confederate soldiers and highlights Key West’s complicated history. Next is Mallory Square. If you’re there at the right time, take part in the famed Sunset Celebration, featuring music, vendors, and other entertainment. Learn how playwright Tennessee Williams started this beloved ritual with a bottle of gin! Walk on to Duval Street, the heart of Key West. Take in some of the many bars and shopping options, including the famous saloon where Hemingway once tossed a few back! Then take a spooky turn at a haunted Hard Rock Cafe. Hear the ghost story that distinguishes this cafe from the others! Next, pass by La Concha Key West, the hotel where Tennessee Williams finished his famed play, A Streetcar Named Desire. As the journey winds down, hear about Mel Fisher and the greatest underwater treasure find of all time! After that, maybe enjoy a cup of Key West’s rich Cuban coffee or delicious key lime pie. Next is the Key West Butterfly and Nature Conservatory, featuring over 50 butterfly species for the insect-inclined. Your tour concludes here.

Find out why Key West attracted so many cultural legends on a self-guided walking tour of the quirky old town. Starting from Mallory Square, follow the precise directions of your audio guide mobile app to learn the fascinating history behind the people and places that make the island so special. Starting from the Memorial Sculpture Garden in Mallory Square, you’ll discover the stories behind Key West’s most famous sights, including the residence of former President Harry Truman, Florida’s oldest bar, the hotel where Tennessee Williams stayed for ten years and the so-called longest street in the world. Along the way, you’ll learn how salvaging shipwrecks transformed the city, why the buildings’ aesthetics are so strictly controlled, how the city became known as the ‘Conch Republic’ and why there are so many chickens running around.

Start your journey at the famous Kino Sandals Plaza, where you will meet with your local guide. On your walk listen to stories about how Key West became one of the wealthiest cities in the mid-1800s. Learn about the island’s shipwrecking industry, sponge harvesting, and cigar manufacturing.  The end of the tour will end at a buoy showing the Southernmost Point of the continental U.S. Here, your guide will give you free maps so that you can continue to explore the various shops,  museums, and other points of interest along this section of the island.

Take a look at the Key West's dark past on a haunted pub crawl walking tour. From the island’s demonic dolls to one infamous case of necrophilia, not everything is glamorous in paradise. Hear all these stories with a drink in your hand as you make your way from bar to bar over an evening. First, head to Captain Tony’s Saloon — Key West’s most eccentric bar with bras on the ceiling and fake bodies beneath the floors. The peculiar tree in the middle of the bar has stained the ground it sits on, its victims still roaming the stools and bottles. Then make your way to Wine-O Bar & Lounge — a staple of Key West’s largest building, La Cocha Hotel. But with great praise comes great tragedy, as being the tallest building makes you a prime candidate for suicide. And with tragic suicides come tragic hauntings. Next, head over to The Roost, which serves some of the best cocktails in Key West. It's also neighbor to one of America’s most haunted city blocks. There, see Key West Theater, a place that houses many shows but used to house children’s screams, and the Artist House, which used to be the home to a cursed doll. Learn about how the Dean-Lopez Funeral Home was once home to a lover’s obsession gone wrong and the lengths he took to bring back the dead. Finally, stroll over to the old-fashioned Old Town Tavern & Beer Garden. You might find the spirit of Ernest Hemingway frequenting it, since his Key West home is right down the street. Hear stories about each haunted location, one drink at a time.

You will begin the 65 minute nighttime guided walking tour by meeting your Tour Guide at Captain Tony Saloon (428 Green Street). You will then be taken to several of Ernest Hemingway haunts around Old Town where he lived, worked and played. You’ll hear incredible stories of history and lore about Hemingway and Key West. This walking tour is easily paced and suitable for most fitness levels. Please wear comfortable clothing and shoes for walking. Are walking tours Would Take place Raynor shine ponchos are provided if necessary.