Florida Keys
Walking Tours

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Our most recommended Florida Keys Walking Tours

Ghosts & Gravestones Tour of Key West

1. Ghosts & Gravestones Tour of Key West

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. 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…

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Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

2. Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

Meet your guide for the night, a world-class drag queen, at the award-winning lounge, Aqua Bar and Nightclub at 711 Duval St. in Key West. Grab a cocktail and mingle with your fellow crawlers as you await the ring of the ‘bitch bell’ to announce the kick-off of the tour. First, follow your guide through the vibrant streets of Key West and prepare to sing and dance your way through the city as you learn how to party like a true queen. Now you know how to behave like a queen it's time to be treated like one too — skip to the front of the line at every bar and pub along the crawl. Then, spend the night at a number of Key West's best bars and clubs, drink delicious and reasonably priced cocktails, laugh with your fellow crawlers, dance like a queen, and experience how the other half lives. Enjoy a fun-filled tour that's perfect for bachelorette parties, birthdays, and other memorable events.

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Key West: Bone Island Haunted Pub Crawl

3. Key West: Bone Island Haunted Pub Crawl

"Cayo Hueso" in Key West, as it was originally named, translates to "Bone Key" or "Bone Island". 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, and after 3 haunted pubs you will be issued a souvenir t-shirt before being released into the night.

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Key West: 2.5-Hour Duval Street Pub Crawl

4. 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.

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Key West: SNUBA Experience

5. Key West: SNUBA Experience

SNUBA is safe family fun and simple to learn. No prior diving or snorkeling experience is required. All necessary equipment is provided and fitted for each guest by a team of professionals. The guests' experience is the number 1 priority, so comfort and safety in the water come first.  After a brief 15-20 orientation during the ride out to the dive site, you'll be ready for an underwater tour through the beautiful local marine ecosystems. SNUBA was created in Hawaii nearly 30 years ago to allow anyone without a scuba certification to fully enjoy the natural wonders that lie beneath the sea. SNUBA arrived in Key West in 1999 and has been continually serving locals as well as visitors on their quests into the underwater world.

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Key West: 3-Hour Guided Bicycle Tour with Key Lime Pie

6. Key West: 3-Hour Guided Bicycle Tour with Key Lime Pie

Meet your friendly guide at the local partner’s office and get kitted out with your bike gear. After a short safety briefing it's time to head out on your island paradise adventure to see the very best that Key West has to offer. The first stop of the tour is the iconic Mallory Square, home to a popular nightly sunset celebration. Here, learn about the island’s history of smuggling and the shipwrecks that have crashed on the nearby reef. Next, pass by the presidential gates that lead to Harry Truman’s Little White House, which is known to have been his favorite vacation spot. Continue the tour onto Mile Marker Zero, which is quite literally the end of the road in the USA, then stop outside Ernest Hemingway’s former home where the famous writer penned many of his treasured novels. Head to the Southernmost Point in the Continental USA for a photo opportunity, then complete your circuit of the island as you ride past Higgs Beach, the White Street Pier, the Key West Cemetery, and the historic Seaport. At the end of an unforgettable 3-hour tour, enjoy a well-deserved rest and a slice of traditional key lime pie, an absolute must for any visitor to the island.

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Truman Little White House: Key West

7. Truman Little White House: Key West

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.

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Key West: Southernmost Food and Cultural Walking Tour

8. 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.

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Key West: Ultimate Parasailing Experience

9. Key West: Ultimate Parasailing Experience

Join the best parasailing experience in Key West for an unforgettable day on the water. Fly the highest and the longest so you get the best views of this tropical paradise. Feel secure with parasailing experts by your side. Prepare for one of the most unforgettable journeys available in the Florida Keys with Key West's parasailing experts. Expect up to 15 minutes flight time and up to an hour total on the boat. As an added perk, grab an optional photo package to remember your experience (available to purchase on board). 

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Key West: Food Tasting and Cultural Walking Tour

10. 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.

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Other Sightseeing Options in Florida Keys

Want to discover all there is to do in Florida Keys? Click here for a full list.

What people are saying about Florida Keys

Awesome for new & experienced riders! Jake & crew were very friendly, fun, patient & professional. Thank you for an excellent ride! I would highly recommend!!! A few things: -Directions to jet ski office is confusing with address given & on Google maps. As you turn right off main rd., "lot 1" with valet parking will be immediately to left. Around the left side of that lot is where office & jet skiing are. Park at closest store. - Only 16+ can drive their own jet ski (but my 15 yo very active son had a blast being on the back!) - Bring towel & wear fitted sunglasses to keep wind out of eyes when riding (it's windy!)

Wear comfortable walking shoes. Don’t be skeptical or make snide comments while guide is speaking. It’s interesting history!

Our tour guide, Bill, was great! We had fun and the bike ride was awesome! Thank you Silvia&Adriano

Bruce was the best tour guide. Very informative and entertaining.

We enjoyed it. Definitely learned things we didn't know.