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24 results | All Key West Tours

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Key West Southernmost Food and Cultural Walking Tour
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Key West Southernmost Food and Cultural Walking Tour

star-5
529
  • 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 Historic Seaport Food Tasting and Cultural Walking Tour
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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 Craft Cocktail Crawl
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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.."


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 Haunted Pub Crawl and Ghost Tour

Key West Haunted Pub Crawl and Ghost Tour

star-4
169
  • 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."


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

star-4.5
1103
  • 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 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 Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
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From
$99.95
Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
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* A traveler said: "The sunset was spectacular. The crew did and excellent job keeping everyone safe and beverages plenty."


Key West Sunset Champagne Catamaran Cruise
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Key West Sunset Champagne Catamaran Cruise

star-4.5
331
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$51.95
From
$51.95
Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.
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* A traveler said: "The crew was amazing, the timing was perfect , we watched the sunset with a beautiful clear sky , we were about 30-35 people enough room for everyone. Bar service excellent"


Key West Sunset Cruise with Live Island Music
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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 Ghost and Mysteries Guided Tour

Key West Ghost and Mysteries Guided Tour

star-4.5
795
  • 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!"


Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

Key West Full-Day Island T'ing Eco-Tour: Sail, Kayak and Snorkel

star-5
424
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$124.95
From
$124.95
Enjoy a day of fun in the sun on the Island T’ing adventure off the coast of Key West. Sail away from the island city of Key West to the beautiful blue waters of the Gulf of Mexico on a large catamaran. Hop in a kayak and enjoy a paddle around a natural stand of mangrove. Look for dolphins, stingrays, sea turtles, manatees and more on this full-day adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.
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* A traveler said: "Great day excursion! Got to see and experience things I never would have otherwise. Crew was fantastic. Highly recommend."


Hard Rock Cafe Key West Dining Experience

Hard Rock Cafe Key West Dining Experience

star-4
27
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$34.49
From
$34.49
At the Hard Rock Café Key West, every meal is an experience, whether on the road or on a lunch break. Dine in style and feel like a star at this popular restaurant, located on world-famous Duval Street in downtown Key West. Savor a 2- or 3-course, fixed-price meal with choice of theme. Enjoy the Legendary Burger, ribs, salmon, steak or a vegetarian option for the main course along with a side and desert. Coffee, tea or soft drink included.
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* A traveler said: "We had a great meal at the hard Rock in Key West! There were no issues exchanging our voucher so it made for a great afternoon escape from the heat. Great memorabilia on the walls and this cafe even has a bit of a colorful history.. Check it out!!"


Yes, Queen! Drag Queen Pub Crawl of Key West

Special Offer

Yes, Queen! Drag Queen Pub Crawl of Key West

star-4.5
9
  • 2 hours
  • Taking safety measures
From
$36.80
$46.00
$9.20 savings
From
$36.80
$46.00
$9.20 savings
Meet your guide for the night, a world-class drag queen, at the award-winning Aqua Nightclub. Grab a cocktail and mingle with your fellow crawlers as you await the ring of the ‘b*tch bell’ to announce the kick-off of the tour. Follow your guide through the vibrant streets of Key West and prepare to sing and dance your way through the city as you learn how to party like a true queen. Now you know how to behave like a queen it’s time to be treated like one too — skip to the front of the line at every bar and pub along the crawl. Spend the night at a number of Key West best bars and clubs, drink delicious and reasonably priced cocktails, laugh with your fellow crawlers, dance like a queen, and experience how the other half live! *Ticket includes tour only. The Cabaret show at Aqua/ 801 Bourbon will not be included, but will have tickets available for purchase*
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* A traveler said: "Drag Queen was entertaining, knowledgeable and all around a great host. Her performance was top notch. Highly recommended when coming to Key West."


Key West Sunset Dinner Cruise with Tropical Buffet
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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."


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

star-4.5
45
  • 3 hours
  • Free Cancellation
From
$93.75
From
$93.75
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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* A traveler said: "Very, very good tour, excellent tour guide, overall a highly recommended tour!"


Private 2-Hour Wind and Wine Sunset Sail in Key West
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Private 2-Hour Wind and Wine Sunset Sail in Key West

star-4.5
15
  • 2 hours
  • Taking safety measures
From
$2,299.00
per group
From
$2,299.00
per group
This trip takes you and your party, (Up to 26 Guests), on a private sunset sail to enjoy wines from around the world and a variety of beers. You will be sailing on a 65-foot schooner while watching the sunset into the ocean. There will be hors d'oeuvres passed around throughout the trip. A great way to have a private sail with your friends, family, or co-workers.
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Hemingway Food and Walking Tour

Hemingway Food and Walking Tour

star-5
13
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$88.00
From
$88.00
This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, his first apartment in Key West where he finished writing “A Farewell to Arms”. Along the way you will have three food samplings, before visiting where he took the train, fished and charted boats in the Key West Harbor, and finally where he spent a lot of time drinking- Sloppy Joe's. An alcoholic drink is also included for you to experience Hemingway's favorite bar. Numerous other historical sites that Hemingway frequented while he lived in Key West will also be visited on this incredibly authentic tour.
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* A traveler said: "Our guide was friendly and knowledgeable.. It was fun to try some local food that was delicious. Great to get some walking in to really get to know Jey West."


Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!
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Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!

star-5
6
  • 2 to 3 hours
  • Free Cancellation
  • Taking safety measures
From
$69.00
From
$69.00
There's so many great places to eat and drink in Key West that it can be difficult to choose. Let this guided tour make the decisions for you. You'll stop into several locals' favorite restaurants to sample cocktails and food before heading to Mallory Square in time for the sunset celebration.
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* A traveler said: "Brian was great and very informative about Key West history. Cocktails and apps were a nice bonus! 😉"


Private Key West Historic Homes and Island History Walking Tour

Private Key West Historic Homes and Island History Walking Tour

star-5
5
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$79.00
Price varies by group size
From
$79.00
Price varies by group size
Historic Homes & Stories of Key West- "2020 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 look behind the scenes of historic Key West. *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 welcoming you and sharing Old Town Key West with you.
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* A traveler said: "Richard had stories for days and makes it well worth taking this tour. Highly recommend this tour as a must!"


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."


Hemingway Walking Tour

Hemingway Walking Tour

star-5
4
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$49.00
From
$49.00
This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, his first apartment in Key West where he finished writing “A Farewell to Arms", where he took the train, fished and charted boats in the Key West Harbor, and finally where he spent a lot of time drinking- Sloppy Joes (the original and the second one). Along the way we will take a break for Key Lime Pie and water. Numerous other historical sites that Hemingway frequented while he lived in Key West will also be visited on this incredibly authentic tour.
More

* A traveler said: "Mark and Carol were awesome in talking about the city and about Hemingway. However- Would have loved to hear more about Hemingway, his specific literary works, what was going on in his life when he wrote his books, and his demise. Also would love it if a tour of his house was included. Overall was an awesome tour!"


Key West Sunset Sip & Stroll Audio Tour

Special Offer

Key West Sunset Sip & Stroll Audio Tour

star-5
1
  • 35 minutes to 2 hours
From
$8.79
$10.99
$2.20 savings
From
$8.79
$10.99
$2.20 savings
Turn your phone or tablet into a local tour guide! This location-aware audio/multimedia tour lets you enjoy historic photos, recordings and videos plus links to happy hour menus and websites at your fingertips. In just 35 minutes of walking, you can cool off at a tiki bar with a gorgeous waterfall, then stroll along a hidden boardwalk with stunning ocean views. Find the best best happy hours with the tastiest seafood snacks. Stroll past Jimmy Buffett’s secret recording studio. Enjoy Key West’s most popular brewery, best mojito, or the world’s yummiest coffee. Learn where locals watch the sun set into the Gulf of Mexico. Sight-see at your own pace, avoid being herded in a crowd, and linger only in the places that truly interest you. Within 24 hours of purchasing (usually sooner,) you'll receive an email with a login address and coupon code giving you access to your tour.
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