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Florida Keys Walking tours

Our most recommended Florida Keys Walking tours

Key West: Ghosts & Gravestones Guided Trolley Tour

1. Key West: Ghosts & Gravestones Guided Trolley Tour

Many find Key West a strange place during the day; but after the sun sets, the restless souls of the island’s frightful past begin to stir. On this 1-hour ghost tour, you will hear all-but-forgotten tales as you travel the dark and narrow streets of the Old Town. Pass 19th-century wooden houses that hold secret stories of former inhabitants; stories so tragic and chilling, you’ll soon see why Key West was named one of the top 10 most haunted cities in America. Learn the sinister story of creepy Count Karl Von Cosel and his dearly departed bride Elena Mesa. Hear tales of lynching, island superstitions, clandestine burials, murder and mayhem. Travel past many of the island's most haunted locations like the Marrero House, the Porter Mansion, and the Hanging Tree. Pass the former home of Robert Eugene Otto, where Robert the Doll suffered the abandonment of his lifelong companion, and his mischievous ways took a more sinister turn. Your Ghost Host will add a pinch of humor to Key West's dark side with tales of deathly love, tragic endings, scores to settle, wrongs to right and ghastly folk - some so strange it will be hard to believe they’re true…

Key West: 2.5-Hour Duval Street Pub Crawl

2. Key West: 2.5-Hour Duval Street Pub Crawl

Come along and do the pub crawl down Duval Street, Key West. This street is famous for its party scene, with the bars always rocking day and night on this small island. Throughout your pub crawl you will experience some of the most famous and entertaining drinking establishments in the Florida Keys. This 2.5-hour event happens on the world famous Duval Street. Everyone will have a choice of a domestic beer or mixed drink at all five bars visited, and you will also receive a free souvenir t-shirt to commemorate the event. Experience all the sites and bars of Key West with your "professional enablers" as you embark on your party in paradise. Whether it's the casual Keys atmosphere, live music, or Caribbean drinks you are after, your crawl is sure to be an adventure to remember.

Key West: Southernmost Food and Cultural Walking Tour

3. Key West: Southernmost Food and Cultural Walking Tour

Celebrating the Cuban and Caribbean influences on both food and culture, enjoy a 3-hour guided small group experience. Visit 5 different locations, carefully chosen to help you check off those "must try" dishes that Key West is known for. Enough for a hearty lunch, tastings are served from locally adored eateries, unique "hole in the walls", and family-owned ethnic restaurants. Discover the spots that the locals frequent to eat, drink and discover the island. Between tastings, explore the island’s different cultural neighborhoods and rich history through the generations. Your knowledgable local guide will share stories of the local industry, Key West's colorful past, and historical landmarks. After the tour, explore Old Town with confidence and take advantage of recommendations on restaurants, attractions, entertainment, and cultural offerings. You'll also receive a collection of exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: Bone Island Haunted Pub Crawl

4. Key West: Bone Island Haunted Pub Crawl

Join us for a ghostly guided walking tour into the heart of old town Key West's most haunted bars. On this haunted pub crawl you will experience why Key West is consistently ranked as one of the top five most-haunted cities in America. Crawl along as you delve into some of the more spirited pubs of Old Town. You'll discover Key West's history of cursed treasure, voodoo, murder, suicide, haunted mansions, unexplained deaths, and more. Your professional "ghost host" will introduce you to the darkest side of "Bone Island" with unbelievable stories of Key West's sinister past. You will receive our signature T-shirt to commemorate the event and cocktails are available for purchase along the way. The crawl ends in the heart of downtown Key West where you will be free to explore more.

The Dark Side of Key West Adults Only Walking Tour

5. The Dark Side of Key West Adults Only Walking Tour

Explore the spooky side of Key West on this ghost-themed adults-only walking tour that visits the city’s popular haunted spots. Become a history buff after learning about the historic events and figures that helped shape the unique culture of Key West. On this adult’s only option that focuses on Key West’s dark and salacious past, you'll discuss Count Von Cosel, Robert the Doll, and The Hemingway House. Hear all about the grisly murders, suicides, demonic deeds, and learn about the fascinating hauntings at each place. Find out the true stories behind these locations and more from a guide who is an expert on the dark, haunted history of Key West.

Key West: Truman Little White House Guided Tour Ticket

6. Key West: Truman Little White House Guided Tour Ticket

Presidents, Prime Ministers and royalty have visited the Harry S. Truman Little White House in Key West. You can be next by taking a tour of this stunning historic building. No trip to Key West is complete without seeing the Harry S. Truman Little White House. Built in 1890 as quarters for the Naval Base Commander and Paymaster, the Little White House has now taken its place in history. In 1912, President William Taft visited the house, and in 1918, Thomas Edison lived there for several months as he worked on inventing new weapons for the war effort. Always at work, the President met with the Joint Chiefs of Staff, worked on the Marshall Plan and the Truman Doctrine, and continually attended to his duties while enjoying the magnificent setting in Key West. It's said that he was friendly with the locals and fit right into the island lifestyle. Today, visitors from all over the world are able to get a glimpse into Truman’s world, see where he and Bess entertained guests, where critical meetings were held, and how the business of our government was conducted in this lovely historic building.

Key West: Old Town Secret Food Tour

7. Key West: Old Town Secret Food Tour

On our Secret Food Tour: Old Town Key West, we'll walk far from the tourist traps of Duval Street to show you the real city and its best food. After our two first delicious bites we take a leisurely walk and explore the history and culture of the city. You'll learn the stories of Key West's luck with affluence and how treasure ignited this tiny island into a global destination. Enjoy tropical soups, mouth-watering appetizers, gourmet tacos, exclusive island sweet treats and lots more. Plus there’s our amazing Secret Dish that you can only find about it on the day!

Key West: Food Tasting and Cultural Walking Tour

8. Key West: Food Tasting and Cultural Walking Tour

Celebrate Key West's diverse and abundant local fruits of the sea. This 3-hour guided small-group experience stops at 6 tasting locations, each carefully chosen to give you an eclectic view of Key West's best restaurants along the historic seaport. Enough for a hearty lunch, tastings are served from adored local eateries, tucked-away hidden gems, and a fisherman-owned seafood market. This tour will allow you to bypass the Duval Street tourist traps and go straight to the spots that the locals frequent to eat, drink, and discover the island. As you stroll the charming side streets and docks, you will experience the island’s seaport, as well as the rich industrial history which has transformed through the generations. Your friendly and knowledgable local guides will share stories of local industry, including the colorful past and historical landmarks. Following the tour, you can explore Old Town with confidence and take advantage of recommendations on restaurants, attractions, entertainment, and cultural offerings. You'll also receive a collection of exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: Off-Duval Cocktail Crawl

9. Key West: Off-Duval Cocktail Crawl

This craft cocktail crawl leads you through the side streets of Key West visiting a fun variety of locally-loved watering holes. Sample fun craft cocktails and tasty gourmet bites on this 3-hour upscale pub crawl. Visit over 5 establishments, ranging from a sleek bar within a historic hospital, a microbrewery inside the birthplace of PanAm, a tiki bar, and more. This tour veers vacationing drinkers off the infamous Duval Street into some of the city’s best and most locally-loved bars to sample fresh spins on old classics. Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era. This bar hop is about getting off the touristy Duval Street and into more local lounges. Between tastings, you will stroll the charming side streets alongside Duval with protected, wild chickens. Your fun and friendly local guides will share bits of the town's colorful past and historical landmarks. Explore Old Town with recommendations on restaurants, attractions, and entertainment. Return home with exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: Ghosts of Key West Walking Tour

10. Key West: Ghosts of Key West Walking Tour

Explore the spooky side of Key West on this ghost-themed walking tour. See the city’s most popular haunted spots and hear fascinating stories about the ghosts of its past. Hear about Robert the Doll, the haunted doll with supernatural powers who sits in the city's East Martello Museum. Stop by the La Concha Hotel and learn about the ghostly legends contained within. See fascinating locations like the Hemingway House and the Artist House. Stroll the city's streets with a guide who is an expert on its dark, haunted history. Become a history buff after learning about the historic events and figures that helped shape the unique culture of Key West

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What people are saying about Florida Keys

Very personable and knowledgeable guide - Chris. Excellent choice of restaurants; delicious food. Great hospitality and service. Only suggestion: End the tour in an air conditioned location that participants can cool off and chill out after the tour is over.

Jim was our Guide for the night. Very knowledgeable of the area. Doll was named after me, thought that was coincidental. Stay off the elevator at one hotel, don't drink too much wine, are safe recommendations for all. Enjoyed!

Great drinks, food. Sara was a great tour guide; gave details on a local could give. Recommend for sure. Bring water, comfortable shoes and get ready to eat!

The experience was awesome. Maxwell knowledge and personal experiences with the various sites made for a most interesting day.

Lots of fun, good interaction guides/customers, 9-year old granddaughter loved it