Looking for fun family activities for your next visit to Key West? Join a guided tour and explore Key West with a real local guide who has insider knowledge of all the hidden secrets in Key West. These tours offer historical information, hidden places, and behind-the-scenes narratives that will make your trip more memorable. This is a fun way to learn about Key West and see the island all at the same time.
Check out our favorite Key West Guided Tours:
Hemingway in Key West Tours
Experience a unique cultural walking tour of the famous stories and songs of Key West. Pick between three different tours; The Hemingway Food & Walking Tour, The Jimmy Buffet Tour, and The Live Music Crawl. Each tour is unique and offers great knowledge of where these two men gained inspiration for their books and music around Key West. Explore where they lived, ate, drank, wrote, and played music. The Live Music Tour is a unique experience for those who love music and the opportunity to experience several different venues in Key West.
Phone: (305) 434-2370
Hidden Key West Walking Tours
Take a stroll with Key West’s “unofficial Mayor" through the historic streets of Old Town. This is a small intimate tour that allows groups to gain insight into the colorful history, unique people, and famous legends of Key West. The carefully crafted routes make this tour of special quality and caliber. The passionate and knowledgeable guides not only tell the story of Key West, but they get into the nooks and crannies of them. Voted Top Tour Guides of North America and Best Highlights Tour of Key West. Tours include The Highlights and Stories of Key West, The Historic Homes and History of Key West, and The Private Haunted Legends of Key West.
Phone: (305) 809-6170
Old Town Trolley
If you are someone who prefers to be chauffeured, The Conch Tour Train is a great way to see all the sites in Key West from the comfort of a fun, air-conditioned trolly. The tour makes 13 stops and is fully curated with historical facts and trivia. You can also hop on and off making it easy to explore and spend more time at the places that interest you the most. The best part is that tickets are good all day, so you can really take your time and make a full day out of it.
Phone: (855) 623-9289
Conch Tour Train
If you’re looking to get a full view of the island, hop on board the Conch Tour Train. This is a 75-minute tour of the entire island of Key West. The train will take you through a tour of the most famous attractions while telling stories of the pirates and wreckers who once controlled the island. The train has open-air seating making it ideal for picture taking. The tour begins at Front Street and will make three designated stops along the way before it ends at Mallory Square. This tour covers the entire island of Key West, not just the downtown areas.
Key West Cemetery
Originally founded in 1847, the Key West Cemetary is located in a residential neighborhood in Old Town. The entrance to this 19-acre cemetery can be found at the corner of Angela Street and Passover Lane and marks the highest elevation on the island of Key West. Here, you can pick up a free guide to help you navigate through the grave sites. Find the famous names of Sloppy Joe Russell, Ellen Mallory, and William Curry. There is much to learn from walking through this crowded cemetery in the heart of Old Town.
Phone: (305) 292-6718, (305) 809-3986.
Ghosts & Gravestones of Key West
This tour is a trolly tour through the dark side of Key West. Your tour guide, or Ghost Host, will meander through the streets of Key West telling tales of tragedy and murder, while exposing haunted sites. Learn what Captain Tony’s Saloon was before it became a famous bar. The tour is complete with a Ghost Meter as many have reported experiencing ghosts throughout the tour. This tour is not recommended for children under 13 years old.
Phone: (866) 955-0668
Food & Walking Tours of Key West
This wonderful food tour is a cultural experience that celebrates the Cuban influences in Key West. The small, guided group will stop at 5 locations to enjoy the authentic island flavors. Learn about Conch Fritters, Key Lime Pie, local fish, and island rum. Learn fun facts while being emersed in the sweet and savory flavors of Key West. The tour will last approximately 3 hours and will include 4 food tastings and 1 alcoholic beverage.
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Key West Art Walk
The Key West art scene is a busy one. Creative souls from all walks of life have been making Key West their home for years. One of the best ways to get to know their works is through a guided art walk. This is a two-hour tour that provides access to active art studios throughout Key West. Find the oldest gallery, resident artists, local art galleries, and more. Curated by a true local, born and raised, you will learn about the history of art in Key West and how these locals share their art and love for the island home.
Phone: (305) 850-8343
Key West Bike Tours
A fun way to see the island is on a bike tour. You’ll see all the famous sites in Old Town while learning about the history of the island of Key West. The knowledgeable tour guides will also clue you into local hotspots and hidden gems off the beaten path. Enjoy a leisurely ride through the streets of Key West and learn about tropical plants, fruits, flowers, and the original architecture. Some tours end with a tropical drink or a slice of Key Lime Pie.