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46 results | All Key West Tours

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Key West Southernmost Food and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Southernmost Food and Cultural Walking Tour

star-5
528
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
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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* A traveler said: "Our guide, Kayla, and the others on the tour were the favorite parts. The food and visits were great, too. This is my 3rd food tour and it was a wonderful experience."


Key West Ghost and Mysteries Guided Tour

Key West Ghost and Mysteries Guided Tour

star-4.5
794
  • 1 hour 30 minutes
  • Free Cancellation
From
$32.26
From
$32.26
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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* A traveler said: "We had a great time learning and hearing the stories of Key West! Ted was great and very knowledgeable!"


Guided Bicycle Tour of Old Town Key West

Guided Bicycle Tour of Old Town Key West

star-5
1221
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.81
From
$49.81
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.
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* A traveler said: "Yvonne was amazing very knowledgeable in the history of the Keys and in keeping a timely tour and the key lime pie was amazing!!!!"


Key West Historic District Small-Group Walking Tour

Key West Historic District Small-Group Walking Tour

star-5
28
  • 2 hours
  • Free Cancellation
From
$46.99
From
$46.99
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.
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* A traveler said: "We had a wonderful time. Our guide was very knowledgeable and professional. The in-depth history of the island and architectural descriptions were excellent."


Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
Likely to Sell OutLikely to Sell Out

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-4.5
1102
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
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.
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* A traveler said: "Had the best time. Great staff, good food, music and food. And the view was absolutely beautiful!! I would totally recommend this trip!! Well worth the money."


Key West Hop-On Hop-Off Trolley Tour

Key West Hop-On Hop-Off Trolley Tour

star-4.5
521
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.35
From
$50.35
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.
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* A traveler said: "Very good experience. Funny commentary and informative. Easy on and off. Good experienced driver. Polite and informative agents at ticket booth also."


Key West Ghosts and Gravestones Trolley Tour

Key West Ghosts and Gravestones Trolley Tour

star-4
280
  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$38.80
From
$38.80
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.
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* A traveler said: "It was so much intriguing information at once. So fun in one hour. Our tour guide was amazing. She took us through the haunted maritime museum and honored the African Americans that were refugees in Key West. So patient with all of our questions"


Key West Historic Seaport Food Tasting and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Historic Seaport Food Tasting and Cultural Walking Tour

star-5
239
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
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, 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 10 people to ensure personal service from your guide.
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* A traveler said: "The food at each stop was excellent. Our guide Dana was very hospitable and knowledgeable of the local history and made the experience very memorable."


Key West Sunset Cruise with Live Island Music
Likely to Sell OutLikely to Sell Out

Key West Sunset Cruise with Live Island Music

star-4.5
475
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$73.75
From
$73.75
Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.
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* A traveler said: "The band and crew were extremely friendly & fun. My sister and I enjoyed the music, breath taking views and wine."


Key West Pub Crawl

Key West Pub Crawl

star-4.5
152
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$34.99
From
$34.99
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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* A traveler said: "Drinking while learning local history and traditions- what a great combination! Our tour guide was fun, friendly and informative. We were in a pretty large group of strangers but it seems that everyone had a great time."


Key West Historic Homes and Island History - Small Group Walking Tour

Key West Historic Homes and Island History - Small Group Walking Tour

star-5
48
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
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.
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* A traveler said: "What a wealth of knowledge Richard has about Key West! His tour is excellent and all the homes we saw were new to us. He does not disappoint! This is a great tour to take at the beginning of your stay so you can learn as much as possible and enjoy Key West to the fullest."


Key West Sunset Dinner Cruise with Tropical Buffet
Likely to Sell OutLikely to Sell Out

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
411
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$88.95
From
$88.95
Watch Key West's sunset — a main island attraction — on an evening dinner cruise. Feast on a tropical-themed buffet dinner and sip provided cocktails, beer, wine, and soft drinks as you take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere, and a cash bar is also available for premium drinks.
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* A traveler said: "We had so much fun dancing to the wonderful live reggae music while we watched the beautiful sunset. The food was excellent and there was plenty of it. We loved being welcomed on the boat with a tasty cocktail! The staff were all friendly with smiling faces. Thank you for a great vacation memory."


Harry S. Truman Little White House Admission Ticket

Harry S. Truman Little White House Admission Ticket

star-4.5
157
  • 1 to 2 hours
  • Free Cancellation
  • Taking safety measures
From
$24.67
From
$24.67
Discover an important part of Florida’s history with admission to the Harry S. Truman Little White House. This former naval base compound is now a treasured museum, open to educating the public about its past and present. See where President Truman retreated for rest and relaxation during his term in office. Learn about the notable people who visited, including Thomas Edison and Dwight D. Eisenhower. And listen to the stories told by those historians who not only know what happened here, but when and why.
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* A traveler said: "Excellent guide and super easy entrance with the prepaid voucher. There was shaded seating to wait for the tour and water and soft drinks could be purchased in the gift shop. The tour itself was informative and covered a lot of Truman era history that is still relevant today."


Key West Craft Cocktail Crawl
Likely to Sell OutLikely to Sell Out

Key West Craft Cocktail Crawl

star-5
128
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
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.
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* A traveler said: "The Tiki Hut and the volcano. Enjoyed hearing about the history of the island. The brewery was very interesting and the beer was good.."


Highlights and Stories of Key West - Small Group Walking Tour

Highlights and Stories of Key West - Small Group Walking Tour

star-5
42
  • 2 hours 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Key West Highlights and Stories- “2020 WINNER Best Key West Walking Tour" Join our award-winning guides for a wonderful, fun, and informative 2.5 hour stroll through the historic streets of Old Town Key West. Our goal is for you to have a fantastic time as your local guide brings to life the rich and colorful history, legends, points of interest, flora/fauna, and culture that make Old Town Key West unique and famous across the globe. There's something for everyone to enjoy on this fascinating and story-filled look behind the scenes of historic 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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Mel Fisher Maritime Museum Admission Ticket

Mel Fisher Maritime Museum Admission Ticket

star-4
52
  • 1 to 2 hours
  • Free Cancellation
  • Taking safety measures
From
$17.50
From
$17.50
Relive the life of one of history’s most famous treasure hunters along with a wealth of exhibits on shipwreck archaeology with this admission to the Mel Fisher Maritime Museum. This Key West institution showcases a variety of treasures, both cultural and monetary, recovered from the treasure and slave ships that once plied the waters near the Florida coast. Check out the thought-provoking Slave Ship and Key West African Cemetery exhibits, then gaze in wonder at the magnificent gold, silver and jewels of the Spanish Treasure Galleons galleries.
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* A traveler said: "Very Interesting. (Happy they had chairs for my parents to sit every now and again). Having the actual items from the sea, to see, was amazing. The story was wonderful. So well defined and elaborate. The slave trade information was unnerving but very educational. Cuban missle crisis review was wildly informative. We enjoyed the museum immensely."


Key West Shipwreck Treasure Museum Admission Ticket

Key West Shipwreck Treasure Museum Admission Ticket

star-3.5
33
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$17.19
From
$17.19
Discover a vital part of Florida’s history with admission to the Key West Shipwreck Treasure Museum. Explore two floors of artifacts from shipwrecks spanning 400 years, featuring treasures from the Spanish fleets of the 1600 and 1700s. Visit the 65-foot lookout tower that offers a spectacular view of the island. Check out the variety of audio-visual displays, including a below-sea-level theater, while storytellers in period costumes bring history to life with tales of the wreckers and their daring rescues. It’s a fun and fascinating experience for the entire family.
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* A traveler said: "had a very good visit , excellent displays parking was a pane good place to visit when in Key West,,,,"


Tiki Cocktail Class in Key West

Tiki Cocktail Class in Key West

star-4.5
32
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$60.00
From
$60.00
Discover the art of Tiki cocktails during a 2-hour class in Key West. Begin with a rum tasting, then learn how to prepare four different drinks, including a Mai Tai. Each cocktail is yours to enjoy, of course. You even learn how to safely light drinks on fire. Class includes: 1 rum tasting and 4 cocktails!
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* A traveler said: "Great experience and Brad was a Fantastic! Funny, knowledgeable and helped us make awesome drinks. Best thing we did this week in Key West!"


Key West Conch Tour Train

Key West Conch Tour Train

star-4
196
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$39.85
From
$39.85
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.
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* A traveler said: "Drivers were informative and humorous . Could suggest making more stops. We would do it again. Nice way to see where you want to spend your time."


Key West Haunted Pub Crawl and Ghost Tour

Key West Haunted Pub Crawl and Ghost Tour

star-4
168
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$22.62
From
$22.62
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.
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* A traveler said: "We had an awesome time! Thanks so much Kelly for a great time! Lots of fun facts we had no idea about."


Beach Day in Key West with Picnic Lunch

Beach Day in Key West with Picnic Lunch

star-5
29
  • 3 to 5 hours
  • Free Cancellation
From
$125.00
From
$125.00
Visit Fort Zachary Taylor Historic State Park on a tour that introduces you to both the history and natural beauty of Key West. Located on the southwestern tip of the island, the park is a relaxing place to spend a few hours snorkeling, sunbathing, and discovering historical sites. This tour provides an easy way to see more of Key West for those short on time.
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* A traveler said: "Excellent beach day! Just a little wind but the wind kept it cool (Margaret was great at reaching out and rescheduling our day to avoid rainy weather) Got a little history of Fort Zachary Taylor Lunch was great too Perfect to show up at the beach and have chairs, umbrellas, towels and snorkeling gear ready for us! Would do it again!!"


Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

star-5
16
  • 2 hours 30 minutes
  • Free Cancellation
From
$224.99
per group
From
$224.99
per group
You will sit and relax on our spacious and comfortable tiki bike 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. This tour includes a slice of famous Kermit's Key Lime Pie for each of you and a complimentary bottle of water!
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* A traveler said: "Very enjoyable and informative tour . It was nice to get away from the crowds and ride through the beautiful streets ."


Private Highlights and Stories of Key West Walking Tour

Private Highlights and Stories of Key West Walking Tour

star-5
5
  • 2 hours 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$79.00
Price varies by group size
From
$79.00
Price varies by group size
Key West Highlights and Stories Private Tour- “2020 WINNER Best Key West Walking Tour" Join Key West's unofficial "mayor" on a wonderful 2.5 hour private stroll through the historic Old Town streets. Our goal is for you to have fun while enjoying the rich and colorful history, legends, 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 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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* A traveler said: "Richard was a fantastic story teller and even kept the attention of our two teenagers! It was the perfect amount of time, history and facts. The distance walking was very doable too."


The Dark Side of Key West Ghost Tour

The Dark Side of Key West Ghost Tour

star-4.5
71
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$34.99
From
$34.99
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.
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* A traveler said: "We really enjoyed the tour. The history is fascinating. Laura is a great tour guide. It lasts an hour and a half and it's a nice walk around the different haunted locations. We had a nice sized group and i'm happy to see people out and about doing this tour! Book it, great time guaranteed!"


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