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Top Key West Cruises, Sailing & Water Tours

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Key West Sunset Champagne and Appetizers Cruise

Watch the sun set and the moon rise off the coast of Key West on this 2-hour sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 60-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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$63.00 USD
From  
$63.00 USD
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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  
$112.95 USD
From  
$112.95 USD
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Dry Tortugas National Park Day Trip by Catamaran

Escape to the secluded islands and tropical beaches off the coast of Key West on this guided, full-day adventure to historic Dry Tortugas National Park. History buffs and outdoor enthusiasts alike will love this unique voyage, where getting there is half the fun on board the Yankee Freedom III, a luxurious, state-of-the-art catamaran. Enjoy snorkeling (equipment provided) in the crystal blue waters and take in the military fort, national park, campground, sandy beaches and coral reefs that make this area special. Breakfast and lunch included.
  • Duration: 10 hours
  • Free Cancellation
  • Duration: 10 hours
  • Free Cancellation
From  
$178.99 USD
From  
$178.99 USD
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Key West Sunset Party Cruise

Jam to island beats by live musicians, eat, drink, and watch the sunset on this classic 2-hour party cruise from Key West. Unlimited drinks and appetizers included; multiple departure times available to suit your schedule.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$58.00 USD
From  
$58.00 USD
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Champagne Celebration Sunset Cruise

Escape to the still waters off the coast of Key West on this 2-hour, adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
  • Duration: 2 hours
  • Duration: 2 hours
From  
$79.49 USD
From  
$79.49 USD
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Half-Day Cruise with Kayaking and Snorkeling

Get ready for fun in the sun on this half-day sailing, kayaking and snorkeling adventure off the coast of Key West. Choose from a morning or afternoon excursion and set sail. Kayak through a maze of mangrove-canopied canals and streams, home to a tropical array of birds, rays, sharks, sport fish and more. Then jump into the water for a snorkeling session above a coral reef with 600 different species of marine life. Relax, feel the warm sea breeze and enjoy the day. Snacks, beer, wine, sodas and water included.
  • Duration: 4 hours 30 minutes
  • Free Cancellation
  • Duration: 4 hours 30 minutes
  • Free Cancellation
From  
$86.00 USD
From  
$86.00 USD
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Key West Day Trip

Kick back in Key West with this island day trip from Miami, and do as little or as much as you like. After an air-conditioned journey by bus that crosses the famous Seven Mile Bridge, enjoy up to six hours of free time. Make the most of the laid-back vibe and explore at your own pace, or upgrade to include an activity such as a conch train ride, trolley tour, parasail ride or snorkel cruise. Want to see the coral reef but don’t want to get in the water? Do the glass-bottom boat cruise instead.
  • Duration: 12 hours
  • Free Cancellation
  • Duration: 12 hours
  • Free Cancellation
From  
$69.00 USD
From  
$69.00 USD
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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 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  
$91.38 USD
From  
$91.38 USD
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Key West Glass-Bottom Boat Tour with Sunset Option

For the aquatic adventure of a lifetime, take this 2-hour cruise to North America's only living coral barrier reef. No need to go scuba diving or snorkeling for this great view — from the deck of a glass-bottom catamaran boat, see more than 600 species of tropical fish, sharks, turtles, lobsters and crabs, plus colorful coral and a vast collection of other sea life. Upgrade to a sunset cruise to enjoy Champagne and soft drinks as the sun settles into the Gulf of Mexico.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$46.96 USD
From  
$46.96 USD
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Key West Backcountry Schooner Eco-Tour

Explore the patch reefs, mangrove islands, and waterways of Key West on a 6-hour cruise and snorkeling tour aboard a wooden sailing schooner. Take a hand at the wheel on your way across the Gulf of Mexico, kayak through the mangroves, then snorkel through patch reefs and sponge gardens. This 6-hour tour includes breakfast, lunch, and access to an open bar on the return sail to Key West.
  • Duration: 6 hours
  • Free Cancellation
  • Duration: 6 hours
  • Free Cancellation
From  
$109.95 USD
From  
$109.95 USD
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Key West Dolphin Watch and Snorkel Cruise

Get ready for fun in the sun on this 3-hour dolphin watch and snorkeling adventure off the coast of Key West. Sail away from the island city of Key West and see dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breeze and select from a variety of refreshing beverages on board the boat.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$77.35 USD
From  
$77.35 USD
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Wild Dolphin Sail & Shallow-water Snorkel

Swim with the dolphins on this 4-hour adventure off the coast of Key West, Florida. Sail away from the island city of Key West to the beautiful blue waters off the coast on a large catamaran. See dolphins swimming and jumping alongside the boat, then jump in for an easy shallow-water snorkel above a coral reef, shipwreck, or sponge garden, all supporting over 600 species of marine life. Relax, feel the warm sea breeze and enjoy light snacks and a variety of refreshing beverages on board the boat.
  • Duration: 4 hours
  • Duration: 4 hours
From  
$95.59 USD
From  
$95.59 USD
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Key West Sunset Champagne Cruise

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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$42.95 USD
From  
$42.95 USD
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Schooner Appledore Key West Cruise

Set sail on the schooner Appledore for a two-hour cruise from Key West!.  Join the crew to raise the sails, take a turn at the wheel, or just soak up views of the scenic Florida coast. Choose a day sail for maximum sunshine, or opt for a sunset sail in the early evening, then enjoy a selection of drinks during your time on the water.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$39.95 USD
From  
$39.95 USD
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Key West Sunset Dinner Cruise

Watch Key West's sunset — a main island attraction — on a 2-hour 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.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$63.43 USD
From  
$63.43 USD
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Sunset Sail in Key West with Cocktails and Hors D'oeuvres

Enjoy sunset from the water on this 2-hour Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, you'll 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 on board. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$75.95 USD
From  
$75.95 USD
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NEW TO VIATOR

Key West Sunset Cocktail Cruise

After a long day of work or sightseeing, treat yourself to a relaxing 2-hour sunset cruise in Key West. Climb aboard the 47-foot catamaran and set sail along the scenic Floridian coast as the sun sinks into the water. Enjoy unlimited South Florida craft beer, California wine, and hand-crafted cocktails for the duration of the tour. A selection of fresh bread and spreads are also provided.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$42.00 USD
From  
$42.00 USD
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Key West Sail and Snorkel Trip from Miami

Get ready for fun in the sun on this day trip and snorkeling adventure off the coast of Key West from Miami. Ride across 32 islands from Miami to Key West, explore the island city, then sail away on a 2-hour cruise on board a spacious 50-foot catamaran vessel. Jump into the water off the coast for a 1-hour snorkeling session above a coral reef with 600 different species of marine life. Professional snorkeling instruction provided. Relax, feel the warm sea breeze and enjoy the day. Miami hotel pickup and drop-off included.
  • Duration: 12 hours
  • Free Cancellation
  • Duration: 12 hours
  • Free Cancellation
From  
$119.00 USD
From  
$119.00 USD
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All-In-One Sail, Kayak, Snorkel aboard 32' Java Cat

Snorkel, kayak, and cruise on this 4.5-hour tour of Florida's Key West National Wildlife Refuge. Set sail on a chartered catamaran from the city’s historic seaport, and take a relaxing 1-hour ride before you drop anchor. Spend some time kayaking around the mangrove islands, and spot sea life native to the area as your group stops in clearer waters to snorkel. Cruise back to the seaport while enjoying a relaxing catered lunch. 
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$123.63 USD
From  
$123.63 USD
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All Inclusive Water Adventure Excursion in Key West

Enjoy a day of sailing, snorkeling and kayaking on this 6.5-hour cruise off the coast of Key West. Spend a relaxing time on board a boat headed to the Key West National Wildlife Refuge. Pass some of Key West’s top attractions, then dive into the water to see more than 600 species of colorful fish, coral and other sea life. Then sail deeper into the refuge for some kayaking. This cruise includes a buffet lunch with unlimited beer, wine and soft drinks to sample along the way.
  • Duration: 6 hours 30 minutes
  • Free Cancellation
  • Duration: 6 hours 30 minutes
  • Free Cancellation
From  
$129.00 USD
From  
$129.00 USD
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Small-Group Sunset Sail with Wine

Escape to the still waters off the coast of Key West on this 2-hour, small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers. Also included is a gourmet cheese buffet and other appetizers, like summer sausages, water crackers with brie, green apples with a honey drizzle and more. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$91.38 USD
From  
$91.38 USD
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Key West Sail and Snorkel Day Trip from Fort Lauderdale

Embark on a tropical adventure with this all-level snorkeling sail trip from Fort Lauderdale! Spend three hours on a 50-foot (15-meter) catamaran, sailing the Florida Keys’ crystal waters with expert guides who offer insight about the surrounding area. At the diving location, don your snorkeling gear and hop into the water to spot brilliantly colored coral and tropical marine life. You’ll also have plenty of independent time to explore vibrant Key West.
  • Duration: 15 hours
  • Free Cancellation
  • Duration: 15 hours
  • Free Cancellation
From  
$149.00 USD
From  
$149.00 USD
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Key West Sunset Snorkel Sail

Combine two activities into one tour and save with this Key West sunset snorkel sail. Not only will you get to relax and listen to the music as you cruise on the Atlantic Ocean during sunset, but you’ll also get to snorkel in a nearby coral reef. Beverages and snorkel equipment are included for added convenience.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$52.68 USD
From  
$52.68 USD
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Key West Sunset Cruise

Celebrate the sunset in Key West with this cruise aboard a 65-foot (20-meter) custom-built Gold Coast yacht. Passengers can enjoy the air-conditioned main cabin or opt for outdoor seating on the upper deck. Live music and complimentary draft beer, wine, Champagne, and soft drinks accompany the setting sun.
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$43.00 USD
From  
$43.00 USD
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(888) 651-9785
(888) 651-9785