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Top Florida Sailing Trips

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20 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
From
US$112.00
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  • Duration: 6 hours
  • Free Cancellation
From
US$112.00

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
From
US$86.00
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  • Duration: 4 hours 30 minutes
  • Free Cancellation
From
US$86.00

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
From
US$91.38
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  • Duration: 2 hours
From
US$91.38

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
From
US$45.97
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  • Duration: 2 hours
  • Free Cancellation
From
US$45.97

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
From
US$95.59
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  • Duration: 4 hours
From
US$95.59

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
From
US$129.00
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  • Duration: 6 hours 30 minutes
  • Free Cancellation
From
US$129.00

Private Sailing Trip on Biscayne Bay

See the sites of Miami while relaxing aboard a private sailboat. Cruise on the Biscayne Bay and take in the views of the Miami skyline, Brickell, and Key Biscayne. Pass by lavish mansions, historical landmarks, and the Cape Florida Lighthouse. Choose from several departure times throughout the day, including an evening sail for sunset views.
  • Duration: 2 to 4 hrs
  • Free Cancellation
From
US$425.00
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  • Duration: 2 to 4 hrs
  • Free Cancellation
From
US$425.00

Private Sailing Charter in Miami

Enjoy a private sailing trip on a 40 foot Beneteau sailboat. Customize your own trip with Captain Bill, who's always game to give an impromptu sailing lesson to adventurous passengers—you can even take the helm or help work a wench. Or, just sit back, relax, and take in the sights. Choose a northern or southern route to highlight Miami classics like the skyline, MIllionaire's Row, and the magnificent Vizcaya estate.
  • Duration: 8 hours
  • Free Cancellation
From
US$425.00
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  • Duration: 8 hours
  • Free Cancellation
From
US$425.00

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
From
US$119.00
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  • Duration: 12 hours
  • Free Cancellation
From
US$119.00

Private 90 Minute Customized Sailing Charter

Enjoy a morning or afternoon of sailing on this private, 90-minute cruise off the coast of Key West. Spend a relaxing time on board a boat headed to Sunset Key and the Key West National Wildlife Refuge. Led by a captain and mate, pass some of Key West’s top attractions and look for more than 600 species of colorful fish, coral and other sea life.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From
US$294.99
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  • Duration: 1 hour 30 minutes
  • Free Cancellation
From
US$294.99

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
From
US$99.00
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  • Duration: 6 hours
  • Free Cancellation
From
US$99.00

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
From
US$60.20
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  • Duration: 1 hour 30 minutes
From
US$60.20

Island Adventure Snorkel Kayak and Tour

Get access to a remote nature sanctuary, known only to Key West locals, during this 4.5-hour island adventure Choose to paddleboard, kayak, snorkel, or just lounge on the sandbar and take in the natural ambiance. Snack, lunch, and use of snorkel equipment included; wine and beer available after activities.
  • Duration: 4 hours 30 minutes
  • Free Cancellation
From
US$106.37
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  • Duration: 4 hours 30 minutes
  • Free Cancellation
From
US$106.37

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
From
US$149.00
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  • Duration: 15 hours
  • Free Cancellation
From
US$149.00

Java Cat Sail, Kayak and Snorkel Charter

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
From
US$123.63
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  • Duration: 4 hours
  • Free Cancellation
From
US$123.63

Swim with Whale Sharks All Inclusive Tour from Los Cabos

Get the opportunity to snorkel near the natural habitat of whale sharks during this tour from Los Cabos, including round-trip transport, snacks, lunch, drinks, and even an open bar. First, learn about the whale sharks from a marine biologist on your way to the dive sight, and then head into the water with a professional instructor. Catch sight of the beautiful sea life in its natural habitat, and afterward, relax with a hot shower.
  • Duration: 5 hours
  • Free Cancellation
From
US$330.60
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  • Duration: 5 hours
  • Free Cancellation
From
US$330.60

90-Minute Key West Harbor Sail

Enjoy a private sailing tour in Key West for the chance to get out on the water with a captain on a boat for just you and your family or friends. This short tour allows you to experience sailing in the Keys even if you're limited on time or on a budget.
  • Duration: 1 hour 30 minutes
  • Free Cancellation
From
US$255.38
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  • Duration: 1 hour 30 minutes
  • Free Cancellation
From
US$255.38

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
From
US$52.68
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  • Duration: 3 hours
  • Free Cancellation
From
US$52.68

Private Sail with Reef Eco Exploration

Book a private sailing tour in Key West for the chance to see the marine life around the island. With a captain at the helm of a private boat, you'll sail from Conch Harbor Marina to the Florida Keys National Marine Sanctuary, home to turtles, dolphins, and other sea creatures. After about an hour, arrive at a reef where you can swim and snorkel. Please note, if sailing to the reef isn't possible because of weather, the captain might take you through mangroves, instead.
  • Duration: 4 hours
  • Free Cancellation
From
US$599.99
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  • Duration: 4 hours
  • Free Cancellation
From
US$599.99

Mimosa Day Sail aboard Schooner America 2

Appreciate the sights of Key West from the water on a 90-minute tour aboard the Schooner America 2.0. Your experience comes with complimentary mimosas, wine, beer, and soft drinks, along with a small appetizer plate. Pass by the area’s key landmarks, including Fort Zachary Taylor and Mallory Square. Keep your eyes peeled and you may be treated to dolphin, sea turtle, and water bird sightings.
  • Duration: 1 hour 30 minutes
From
US$60.20
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  • Duration: 1 hour 30 minutes
From
US$60.20


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