Top Key West Walking Tours

Rich in history and culture, Key West's Historic District demands to be explored in the company of someone who knows its stories. This small-group walking tour promises a far richer experience than wandering around alone. As you stroll through the scenic streets, your guide will fill you in on Key West's history, lore and legends.

Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the docks into some of the most colorful neighborhoods in Key West, pausing to sample locally caught pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere.

Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.

Jimmy Buffett has left his mark on Key West since he arrived 50 years ago. If you have a passion for all things Buffett and Margaritaville, this walking tour is the best way to find the locations around Old Key West that inspired his songs. Your guide will also take you to the location of his first gig, some of his favorite watering holes, bars he played in and his recording studio.

Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.

Discover some of Key West’s deepest, darkest secrets on a 60-minute ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of one of the most haunted cities in the country. Experience Key West’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. This tour is narrated by a 17th-century gravedigger guide who’s almost as scary as the stories being shared.

Key West is home to many unique architectural landmarks and historic homes. Rather than wandering around alone, you can learn the fascinating stories of each by taking a guided tour. This small-group walking tour provides in-depth insights into the people and places of historic Key West.

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.

Explore the best that Key West has to offer on this narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Select from an unlimited 1- or 2-day pass to suit your schedule.

Enjoy a morning or afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing time on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life. This cruise includes professional snorkeling gear and instruction plus beer, wine, and soft drinks.

Discover the spooky side to one of the country's most haunted cities on a 90-minute walking tour. Listen to hair-raising local legends as you follow your guide down the hidden alley's of Key West. See where Robert the Doll lived, learn about Count Von Cosel, and keep your eyes peeled for the ghost at La Concha. Learn how to attract spirit activity with dowsing rods and how to capture it with your camera.

Explore Key West through the eyes of a local on a craft cocktail tour that stops at five off–the–beaten–path establishments, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.

Follow in the footsteps of Ernest Hemingway during a walking tour that focuses on food, culture, and history. Exploring Key West on foot means that you'll get a more intimate glimpse into the historic area, which is characterized by its charming bars and plethora of museums. Plus, you'll receive personalized attention as you explore in a small group limited to only 15 other travelers.

Key West has no shortage of ghost tours, but most typically only tell you stories about local ghosts. This tour amplifies the excitement by featuring a ghost hunt. As you visit various haunted locations around Key West, you'll make use of ghost-hunting equipment such as dowsing rods, EMF meters, a spirit board, and more.

It's easy to find the colorful, fun-loving side of Key West, but takes a little more effort to uncover its darker side. This walking tour offers the chance to see Key West in a completely different light. Your guide takes you to landmarks such as St. Paul's Episcopal Church and Capt. Tony's Saloon while discussing the city's spooky, sometimes grisly, history.

From local shrimp to the perfect Key lime pie, Key West dining is a food-lover’s dream, but finding authentic flavors can be a challenge in a town packed with touristy restaurants. Discover the very best bites on a gourmet tour that samples a little bit of everything, exploring Key West’s charming neighborhoods, colorful characters, and history along the way.

Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.

Key West’s Old Town is a wonderfully walkable area that’s best enjoyed at a slow and steady pace. Take advantage of free time under the sun while learning about the history of the island during this self-guided audio tour of Old Town. A tour guide narrates this journey up and down the streets, having you stop at attractions like the Little White House and the Lighthouse. You’ll end your walk at Mile 0: the Southernmost Point of the Continental US.

Key West is a wonderfully walkable island that deserves just as much exploration under the moonlight as it does under the sun. Avoid the crowded group tours and opt for this self-guided ghost tour. Using your smartphone, you’ll explore Key West’s allegedly haunted sites and hear their grizzly histories. Go at your own pace, taking breaks or visiting other Key West attractions as you continue your adventure.

Get a different perspective of Key West and visit some lively local spots at the same time during this haunted pub crawl tour. Take a journey through the streets of Key West as your guide regales you with scary stories. From eerie tales of possessed dolls to creepy encounters with the macabre, enjoy the entertainment as you visit various landmarks.

Explore the streets of Key West on this guided small-group walking tour. As you wander through Old Town, discover the history and culture of the island, which includes tales of shipwrecks, cigar manufacturing, and treasure hunting. Stop at popular attractions such as the Ernest Hemingway Home and Museum, the Southernmost Point, and Audubon House & Tropical Gardens.

Key West is rich in spooky history but you need a local's insight to fill you in. This walking tour is focused on the island city's hauntings and ghost tales. As you visit notable spots such as St. Paul's Episcopal Church and the Audubon House and Tropical Gardens, your guide will shed light on prominent figures and the dark history of Key West.

Don't let the trolley take you for a ride. We're the only ghost tour in Key West where you'll walk the dark halls of historic Fort East Martello with authentic ghost-hunting equipment and meet Key West's infamous haunted doll, Robert. USA Today named us one of America's 10 Most Haunted Destinations, and Thrillist calls us "The Creepiest Place in Florida." See for yourself, but be warned: we actively engage spirits, so our hunts are not for everyone. We're family-owned by real Key West locals, and our Google satisfaction rating is 4.9. One of our owners opened the first ghost tours on the island and wrote Ghosts of Key West, Haunted Key West, and the biography of Robert the Doll. Book General Admission tickets on our site for the one-hour guided tour. Book VIP here for the two-hour ghost-hunting adventure, which includes an additional hour hunting ghosts on your own after the guided tour. There are dozens of ghost tours in Key West. See why people are dying to get into ours.