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18 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
532
  • 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: "Had a great tour experience with Dana. Learned some fun facts and history of Key West while meeting other people and enjoying some great food. Favorites: Cuban food at El Siboney and Jerk Fish at Kaya Island Eats."


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
243
  • 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: "our tour guide Rose was very friendly and knowledgeable about the area. The food was really good! Best part of my trip!"


Key West Craft Cocktail Crawl

Key West Craft Cocktail Crawl

star-5
131
  • 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: "Fantastic experience bopping around the city, seeing landmarks, and trying new drinks. The guide (Rose) was hilarious and engaging and the group we matched up with were fantastic. Would highly recommend!"


Key West Pub Crawl

Key West Pub Crawl

star-4.5
153
  • 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: "Had a ball the Guide was awesome he made all of us laugh had a lot of hilarious jokes brought the group together as one everyone became friends it was a blast I would definitely do this again"


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

Key West Sunset Dinner Cruise with Tropical Buffet

star-4
413
  • 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."


Key West Premium Sunset Sail aboard Schooner with Hors D'oeuvres and Full Bar
Likely to Sell OutLikely to Sell Out
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 Jet Ski Tour: Free 2nd Rider

Key West Jet Ski Tour: Free 2nd Rider

star-5
358
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$173.27
From
$173.27
Discover 28 miles (45 kms) of the Floridian coast on a 1.5-hour jet ski tour. With four daily tours, you can easily find a time that fits with your schedule. The tour is priced per jet ski, so you can ride tandem with a friend at no additional cost. Your guide is on hand at all times to lead the way on your aquatic adventure.
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* A traveler said: "Awesome ride with Jake and BJ.. Tour was a blast and they were very patient. Smooth sailing. Highly recommend."


Key West Haunted Pub Crawl and Ghost Tour

Key West Haunted Pub Crawl and Ghost Tour

star-4
174
  • 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: "Good tour , the host was very funny and worth the price of the tour and we went to to some very interesting places. I would do it again. Thanks Kelly.."


All-Inclusive Water Adventure Excursion in Key West

All-Inclusive Water Adventure Excursion in Key West

star-5
258
  • 6 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$129.00
From
$129.00
Save time and money in Key West on this all-inclusive, full-day excursion. Enjoy a day of sailing, snorkeling, and kayaking off the coast. Visit the Key West National Wildlife Refuge and explore an underwater world full of colorful fish and coral. Includes a buffet lunch with unlimited beer, wine, and soft drinks.
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* A traveler said: "Thanks to Brian, Ellen and Joe we all had a great time. We were lucky to see dolphins and Brian moved the vessel for us to get a better view!"


Shark and Wildlife Viewing Adventure in Key West
Likely to Sell OutLikely to Sell Out

Shark and Wildlife Viewing Adventure in Key West

star-5
729
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$84.27
From
$84.27
Get up close with sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast of Key West. See dolphins, stingrays, turtles and birds and learn about Key West’s waters, and then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat. Bring a camera to capture the excitement as these super predators swarm. Cold drinks, snacks and polarized sunglasses are included on this Key West shark cruise.
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* A traveler said: "This was such an awesome experience! Knowledgeable, friendly and enjoyable tour guides. Made sure everyone was able to get a good view. Clean boat with plenty of seating, shade, and open sides. Saw sharks, sea turtles and jellyfish! Definitely worth the price. Would go again!"


Ultimate Jet Ski Tour of Key West

Ultimate Jet Ski Tour of Key West

star-4.5
303
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$166.57
per group
From
$166.57
per group
Experience Key West’s tropical blue waterways on this Jet Ski tour along the Atlantic Ocean and/or the Gulf of Mexico. Enjoy panoramic island views and watch for dolphins, stingrays, sea turtles, manatees and more while gliding over warm ocean water. Bring a waterproof camera to capture this southernmost point in the continental United States.
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* A traveler said: "Gary and Liam did a great job with the group. I am older (over 60) and went with my sons. I have owned a boat and water-skied in the past; however, it was my first time riding a jet ski. We started out at a slower pace on the gulf and it became more challenging on the Atlantic, with waves, and speeds around 45mph. Fun time!"


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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Private 2-Hour Wind and Wine Sunset Sail in Key West
Likely to Sell OutLikely to Sell Out

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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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 Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!
Likely to Sell OutLikely to Sell Out

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.
More

* 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."


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