Top Key West Cultural Tours

Explore the best that Key West has to offer on this narrated, Conch Train Tour. See Key West’s top attractions and learn about the Conch Republic’s history and residents, past and present. See where Ernest Hemingway used to hang out and find out why Harry Truman used to spend so much time here. Get to know Old Town Key West, from the Front Street Depot to Mallory Square and everything in between, including live onboard commentary from a professional tour conductor. It’s Key West’s original, and most iconic, sightseeing tour.

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.

Eat your way around Key West on this food tour with a guide who introduces you to 'mom and pop' eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and, of course, key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.

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.

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.

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.

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.

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 fish tacos, Key West 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, and group size is limited to 12 people to ensure personal service from your guide.

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.

Swap crowded bus tours for a private and personalized tour of Key West on a comfortable, and unique, tiki bike. Your driver will pedal you around the streets of Old Town and the Historic District to top attractions and places that cannot be reached by bus. You'll also be treated to a slice of famous Kermit's Key lime pie.

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.

Turn your phone or tablet into a local tour guide! Download this location-aware audio & multimedia tour to your device. Local knowledge, historic photos, and links to websites and restaurant menus rest at your fingertips. In just an hour of easy walking, learn the history, culture, and cuisine of Key West, never wasting a step. Visit the most important museums and attractions. Discover the island’s best Key lime pie, Cuban cigars, rum mojitos, craft beer, conch ceviche, fish tacos, and handmade sandals. Learn about famous writers, wreckers, and pirates. End with a swim on a popular beach. Perfect for solo travelers and small groups. Sight-see at your own pace, avoid being herded in a big crowd and only linger in the places that truly interest you. To book, choose any future date. Shortly after booking, you'll receive a confirmation email with login instructions and a coupon code. You can take the tour anytime once you have your unique coupon code

Turn your phone or tablet into a local tour guide! Download this location-aware audio/media tour, then cruise. PLEASE NOTE ELECTRIC CAR, SCOOTER OR BIKE RENTAL IS NOT INCLUDED. Rent from one of the vendors recommended at the beginning of the tour, then sight-see at your own pace. Nowhere will the speed limit exceed 35 mph. Learn about Key West's deep ties to the Bahamas and the city's role defeating the Confederacy. Discover why 250 Africans are buried by the beach, see the surprising tourist spot that was once the island's "blacks only" beach. Find the Keys' best conch salad, get a taste of Haitian and Cuban flavors and sample Key Lime pie. Historic photos plus links to restaurant menus and websites rest at your fingertips. Spend one hour or a whole day. To book, choose any future date. Shortly after booking, you'll receive a confirmation email with login instructions and a coupon code. You can take the tour anytime once you have your unique coupon code.

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.

Slip on a pair of comfortable walking shoes and get ready for an extensive walking tour around Key West. You’ll take a journey through the historic streets of Old Town Key West, accompanied by a local guide and up to nine other travelers. This is a rain or shine tour and rain ponchos are provided if the weather turns sour. Among the many stops you’ll pass by are Truman Annex Park, US 1 Mile Marker 0, and the Southernmost Point.

Make your way to Key West with a smartphone and you’ll have all you need to discover the island’s best foods. This tour is self-guided through your smartphone. Simply follow the instructions that lead you to places like Mallory Square and the Key West Turtle Museum. Photos and audio recordings are available on your phone, as well as happy hour menus for the best restaurants. Pause the tour whenever you want to savor the flavors of Key West.

Key West is filled with rich and spooky history, but ghost tours often lose some of their haunting atmosphere when guests are crowded together in a group. This private walking tour is exclusively for your party so you'll enjoy your guide's undivided attention as they lead you to at least five haunted mansions and two haunted bars.

Travel The Keys is a guided tour and concierge company based in Key West, Florida. We offer unique historical tours in Key West, presented by a 5th generation local. Our tours present a collection of lesser known historical events and explore the cultural legacies of the Southernmost District and surrounding areas of Key West.

Historic Homes & Stories of Key West- 2020 and 2021 WINNER- "Best Key West History Tour" Join our award-winning guides for a wonderful, fun, and informative 2 hour stroll through the celebrated Old Town neighborhoods where you'll discover many of the most beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community. We’ll see the exteriors of a variety of beautiful homes and public buildings, each with its own legendary story, notable history, and rich style. There's something for everyone to enjoy on this fascinating and story-filled look behind the scenes of historic Key West. *Voted Top Tour Guides of North America *20+ years experience *Our guides have been featured in leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. *Not recommended for people with impaired walking ability.

Swap the standard sightseeing tours of Key West for a more personalized experience. This private tour is exclusively for your group and led by a Key West local and unofficial "mayor." As you stroll through the Old Town streets, you'll learn all about the colorful histories and personalities that have shaped Key West.

This private tour is ideal if you want to see it all in Key West, but are not a fan of crowded group tours. In the company of just your group and a guide, hit the streets and stroll to all the top attractions, including the Southernmost Point and Mallory Square. Best of all, the tour can be customized to your own interests.

Tours will begin at the corridor of the Southernmost District near the Key West Lighthouse and the home of the infamous author Ernest Hemingway. We will proceed through the Southernmost District and continue onto the neighborhood where the historic "Bahama Village" remains. Your experience will be provided by a fifth generation native of Key West and will include the history, folklore and architecture of traditional Key West.

Join us for the best walking tour in Key West! You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA! Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States. The private tour is the best way to explore Key West and have fun with your own group of friends or family! Book Now and call us to schedule the time that is convenient for you! This tour includes a slice of Kermit's Key Lime Pie for each traveler & a bottle of water. What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.