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Top Key West Luxury & Special Occasions

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11 Tours and Activities

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Key West Island T'ing: Sail, Snorkel and Kayak Adventure

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. Snorkel above a coral reef. Look for dolphins, stingrays, sea turtles, manatees and more on this guided, 6-hour adventure. A full breakfast and buffet lunch, plus beer, wine, soft drinks and homemade sangria are included.
  • Duration: 6 hours
  • Free Cancellation
  • Duration: 6 hours
  • Free Cancellation
From  
US$ 112.95
From  
US$ 112.95
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Key West Sunset Sail Aboard Schooner America 2.0

Set sail on a replica of the 1851 Schooner America on a 2-hour cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres, along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.
  • Duration: 2 hours
  • Duration: 2 hours
From  
US$ 91.38
From  
US$ 91.38
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Key West Classic Day Sail Aboard America 2.0

Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.
  • Duration: 1 hour 30 minutes
  • Duration: 1 hour 30 minutes
From  
US$ 68.80
From  
US$ 68.80
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NEW TO VIATOR

Key West Secret Food Tour

Soak up the charm of the neighborhood's fully-restored, historically significant Victorian, shotgun, and conch-style homes on tree-lined streets. The area's atmosphere makes it easy to lose yourself in the magic of Key West, immersing yourself in the vibe of the Conch Republic. Let our guide entertain you with funny and interesting anecdotes about this beautiful district
  • Duration: 3 hours
  • Duration: 3 hours
From  
US$ 85.53
From  
US$ 85.53
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Old Town Literary Walking Tour

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.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$ 30.00
From  
US$ 30.00
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NEW TO VIATOR

Key West Morning Boat Charter (up to 6 guests)

We'll begin our adventure by cruising away from the Island of Key West into the crystal blue waters of The Gulf of Mexico. Once underway to our island destination you should be on the look-out for dolphins, manatees, sea turtles, stingrays and more.After arriving you and your family or friends can simply relax or engage in a number of activities including kayaking, paddleboarding and snorkeling. Possibilities abound!Either indulge your sense of adventure or lay back and take it all in. We will see to every detail to be sure you don't have to lift a finger.We provide all equipment and toys:Snorkeling GearKayaks and PaddlesPaddleboardsSwim NoodlesFishing GearWe have room for up to 6 guests per charter.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$ 496.00
From  
US$ 496.00
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NEW TO VIATOR

Sunset Cruise

Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention to detail on our sunset cruise are legendary. Don’t forget your camera!
  • Duration: 1 hour 30 minutes
  • Free Cancellation
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From  
US$ 55.00
From  
US$ 55.00
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NEW TO VIATOR

Small Group Private Key West Tours

See Key West through the eyes of a Piratical Swashbuckling Key West Character. Plenty of pageantry and a plethora of information, eats, drinks and treats will be discovered on your personalized tour.Set your own budget from $400 to 1 Million plus!
  • Duration: 4 to 8 hours
  • Free Cancellation
  • Duration: 4 to 8 hours
  • Free Cancellation
From  
US$ 450.00
From  
US$ 450.00
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NEW TO VIATOR

Luxury Private Yacht Charter

After Hours is Key West's premier motor yacht available for luxury private charters for up to 6 people. Guests are provided food, drinks, and personalized service tailored to their specifications. Host your closest friends and family for an amazing outing that they'll remember for years. Or show your important clients or colleagues how much they are valued with a one-of-a-kind experience. Whatever the occasion, it is our pleasure to arrange the perfect yacht charter for you.Your dedicated, knowledgeable, and local captain can guide you to Key West’s most scenic destinations. Enjoy a drink while laying out on the forward sundeck. Cool off with a swim in crystal clear waters. Take in a breathtaking view from the spacious seating in the sky lounge above decks. Cruise to a secluded island to enjoy a picnic lunch on a beautiful sandy beach. Snorkel and explore the magnificent colors and creatures of a world famous coral reef. Soak in a famous Key West sunset.
  • Duration: 2 hours
  • Duration: 2 hours
From  
US$ 1,177.00
From  
US$ 1,177.00
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NEW TO VIATOR

Key West Afternoon Boat Charter (up to 6 guests)

We'll begin our adventure by cruising away from the Island of Key West and into the blue waters of The Florida Keys. Once underway, you should be on the look-out for dolphins, manatees, sea turtles, stingrays and more.This custom charter will allow you and your family or friends to simply relax or engage in a number of activities including kayaking through an eco-tour in the mangroves, paddle-boarding and snorkeling. Possibilities abound!Either indulge your sense of adventure or lay back and take it all in. We will see to every detail to be sure you don't have to lift a finger.We provide all equipment and toys:Snorkeling GearKayaks and PaddlesPaddle-boardsFloating swim matFishing GearWe have room for up to 6 guests per charter.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
US$ 496.00
From  
US$ 496.00
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NEW TO VIATOR

Bahama Village, Hemingway Museum, and Southernmost Point

We'll begin in old Key West where pirates first discovered the island. We'll stroll along the houses of ship captains and wreckers learning their history and will pause for a photo at Mile 0. We'll pass the historic Courthouse, a centuries old church, and enter Bahama Village and explore this culturally rich African-Caribbean neighborhood. We'll wind our way over to the home where Hemingway wrote many of his novels, stroll past the city's lighthouse, and end the tour at the Southernmost Point landmark.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
US$ 75.00
From  
US$ 75.00
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Book online or call
(888) 680-5731
(888) 680-5731