Florida Keys
Sightseeing Walking Tours

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Our most recommended Florida Keys Sightseeing 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…

Key West: Southernmost Food and Cultural Walking Tour

2. 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.

The Dark Side of Key West Adults Only Walking Tour

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

4. 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.

Key West: Ultimate Parasailing Experience

5. 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). 

Key West: 2.5-Hour Duval Street Pub Crawl

6. 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.

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.

Key West: SNUBA Experience

8. 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.

Key West: Haunted Pub Crawl Walking Tour

9. Key West: Haunted Pub Crawl Walking Tour

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 neighbors to one of America’s most haunted city blocks. There is Key West Theater, a place that houses many shows but used to house children’s screams. And there is 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 Hemmingway frequenting it, since his Key West home is right down the street. Hear stories about each haunted location, one drink at a time.

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.

Frequently asked questions about Florida Keys Sightseeing Walking Tours

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Other Sightseeing Options in Florida Keys

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What people are saying about Florida Keys

Take this food tour, it is great! My friend and I were only in Key West for one full day and this was the perfect way to experience the town. We got to try a much wider variety of food than we would have otherwise during our short trip. The food (and rum) was great, but the walking component was possibly my favorite part. Our guide, Maxwell, was fantastic. He grew up in Key West and was personable and full of stories. He took us all through the historic part of town, which I wouldn't have known to visit if I hadn't done the tour. Maxwell also gave great recommendations for restaurants and bars, so you'll continue to benefit even after the tour is over! I also felt that the price was very reasonable for the amount of food and time (remember to bring cash for a tip, they deserve it!)

I love bike tours as a way of getting to know the city I'm visiting. A little bit of exercise, some history, sights and local recommendations. This tour has it. Honestly, the guide joked about telling us too much history, but I would have loved more. You hit all the highlights of Key West on this tour.

Our guide, James, was very knowledgeable and engaging. He reached out to each member of the group to make sure everyone was having a good time. The leisurely pace made it very relaxing.

James was our guide and he was so funny! Great guy and very knowledgeable. He made the bike ride super fun. Would recommend 10/10.

Puddingtane was amazing! She was hysterical and kept me laughing the whole time.