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17 Key West Cultural Tours | All Key West Tours

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Small-Group Key West Food Tasting and Cultural Walking TourHalf-day Tours

Small-Group Key West Food Tasting and Cultural Walking Tour

star-5
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.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$88.68
From
US$88.68
Taking safety measures

Key West Ghost and Mysteries TourCultural Tours

Key West Ghost and Mysteries Tour

star-4.5
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.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$32.26
From
US$32.26
Taking safety measures

Southernmost Key West History and Culture Small-Group Walking TourPrivate and Luxury

Southernmost Key West History and Culture Small-Group Walking Tour

star-5
Key West is open to visitors starting June 1, 2020, and we are very excited to have you on one of our tours! Join us for a 1.5-hour adventure! Our tour is led by knowledgeable local guides. As we walk through the streets of Key West’s old town, you will discover the history and culture of our island. Shipwrecking, sponging, cigar manufacturing, treasure hunting - it’s all about Key West! What to bring: Hat, sunglasses, and sunblock is a must. Bring at least one bottle of water for yourself. Wear comfortable clothing and shoes. Sneakers are the best option. Camera or your phone to take pictures. Your adventurous spirit :)
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$30.21
From
US$30.21

Key West Craft Cocktail CrawlHalf-day Tours

Key West Craft Cocktail Crawl

star-5
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 three gourmet food tastings.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$88.66
From
US$88.66
Taking safety measures

ConchTales and Dreams: Food, Drink and Fun Tour of Key WestHalf-day Tours

ConchTales and Dreams: Food, Drink and Fun Tour of Key West

star-4.5
Get to know the sights, sounds and tastes of Key West on this guided, 3-hour, small-group tour. Enjoy three drinks and three food tastings at some of the best pubs, dives and diners in Old Town and the Historic Seaport at Key West Bight Marina. Also, visit the Key West Legal Rum Distillery for a tour and tasting. Along the way, learn about the rich history and traditions of this island city, whose visitors have included fortune hunters, wreckers, spongers, pirates, tobacconists, artists, poets and writers.
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  • 3 hours
  • Free Cancellation
From
US$93.75
From
US$93.75

Key West Historical Seaport Food Tasting and Cultural Walking TourHalf-day Tours

Key West Historical Seaport Food Tasting and Cultural Walking Tour

star-5
Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the beach and docks into some of the most colorful neighborhoods in Key West, pausing to sample locally-caught fish tacos, Key West pink shrimp, conch ceviche, 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 homemade sangria 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 10 people to ensure personal service from your guide.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$88.68
From
US$88.68
Taking safety measures

Old Town Key West Literary Walking TourPrivate and Luxury

Old Town Key West Literary Walking Tour

star-5
Explore the literary highlights of Key West during this walking tour, inspired by David A. Kaufelt’s original literary walking tour. An in-the-know guide whisks you around the Old Town to the former homes and favorite haunts of writers that have called the island home, including Shel Silverstein, Tennessee Williams, and Robert Frost. Since this is a small-group tour, you’ll have plenty of time to ask questions, too.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$30.00
From
US$30.00

Key West Pub CrawlBeer & Brewery Tours

Key West Pub Crawl

star-4.5
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.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$34.99
From
US$34.99
Taking safety measures

Key West Conch Tour TrainCultural Tours

Key West Conch Tour Train

star-4
Explore the best that Key West has to offer on this narrated, Conch Tour Train excursion. Visit 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 sightseeing tour.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$36.70
From
US$36.70
Taking safety measures

Southernmost Key West Historical Tour in Small GroupCultural Tours

Southernmost Key West Historical Tour in Small Group

star-3
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.
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  • 1 minute to 1 hour 30 minutes
  • Free Cancellation
From
US$32.50
From
US$32.50

Private Key West History and Culture Rickshaw Experience Private Sightseeing Tours

Private Key West History and Culture Rickshaw Experience

star-5
You will sit and relax on our spacious and comfortable Rickshaw as your private guide/driver takes you on a pleasant ride around the enchanting streets of Old Town and Historic District. Experience its amazing architecture and historic sites as you learn the rich history, culture, and folklore of our beautiful island of Key West. First-row, Historic, Cultural and Fun, the only VIP experience tour in Key West.
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  • 2 hours
  • Free Cancellation
From
US$189.00
per group
From
US$189.00
per group

Afternoon Delights: Small-Group Food and History Tour of Key WestHalf-day Tours

Afternoon Delights: Small-Group Food and History Tour of Key West

star-5
A short walk between stops include points of interest like architeture, flora and fauna. Local history as well as bumping into some characters of Key West are always interesting. Discover some mansions and eateries that you may not find on your own.
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  • 3 hours
  • Free Cancellation
From
US$89.00
From
US$89.00

Private Southernmost Key West History and Culture Walking TourPrivate Sightseeing Tours

Private Southernmost Key West History and Culture Walking Tour

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! What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
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  • 2 hours
  • Free Cancellation
From
US$238.55
per group
From
US$238.55
per group

Key West History and Culture Small-Group Walking TourPrivate and Luxury

Key West History and Culture Small-Group Walking Tour

star-5
Key West is open to visitors starting June 1, 2020, and we are very excited to welcome you on 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. What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
More
  • 2 hours
  • Free Cancellation
From
US$39.99
From
US$39.99

Cultural Walking Tour of Key West with Food and Drink TastingsHalf-day Tours

Cultural Walking Tour of Key West with Food and Drink Tastings

Discover the cuisine and culture of historic old Key West. Tastings of authentic dishes like Cuban pork and Key lime pie. Stops at local haunts like Mangoes, Blue Heaven and Rum Bar. Guided historical and cultural walking tour. Chance to navigate the city's charming streets like a local
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  • 3 hours
  • Free Cancellation
From
US$240.00
From
US$240.00

Highlights of Key West Walking TourBeer & Brewery Tours

Highlights of Key West Walking Tour

Key West Highlights- “The best tour in Key West!” Join Key West's unofficial "mayor" and his sidekick "Oliver" (Key West's most famous mascot) as they take you on a pleasant 2 hour stroll through the historic Old Town streets. Our goal is for you to have fun while enjoying the rich and colorful history, legends, food, points of interest, and culture that make Old Town Key West unique and famous across the globe. The quality of our tours and our guides is unmatched on the island. With unique insights and carefully crafted tour routes, we strive to provide the very best walking tours available in Key West. *Consistently ranked as the top “Highlights Tour” by Keys Tourism Association *Voted Top Tour Guides of North America *Over 20 years experience *Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. We look forward to sharing Old Town Key West with you.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$49.00
From
US$49.00
Taking safety measures

Private Walking Tour of Key WestPrivate Sightseeing Tours

Private Walking Tour of Key West

Walk through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. **If it's too far or too hot to walk, you have the option of hopping on the Duval Loop bus with your guide for only $1 per person** It's air-conditioned with several convenient stops throughout Old Town. These tours are private so you can ask questions and we can customize the tour to your interests. Your tour guide is knowledgeable about everything Key West, so don't hesitate to let us know what interests you and what you want to know about Key West.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$69.00
Price varies by group size
From
US$69.00
Price varies by group size
Taking safety measures

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