Top Florida Sailing Trips

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

• 97 Reviews
• 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.
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Half-Day Cruise with Kayaking and Snorkeling

• 30 Reviews
• 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.
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All-In-One Sail, Kayak, Snorkel aboard 32' Java Cat

• 2 Reviews
• 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. 
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Key West Classic Day Sail Aboard America 2.0

• 4 Reviews
• 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.
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Key West Sunset Sail Aboard Schooner America 2.0

• 9 Reviews
• 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.
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Sunset Sip & Sail

• Planning a night out in Key West with entertainment can add up quickly. This Key West cruise saves you money by combining an open bar with musical entertainment as you sail the waters keeping an eye out for views of the sunset. Plus, it ends early enough to leave you enough time to bar hop afterward if you’d like.
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Surf Lessons

• A must do. Everyone can surf and the enjoy the ocean whether you surf, snorkle, kitesurf, or paddleboard. The ocean and experience is by far something worth doing, extremely healthy and absolutely fun for the entire family
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Wild Dolphin Sail & Shallow-water Snorkel

• 37 Reviews
• 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.
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Schooner Appledore Key West Cruise

• 12 Reviews
• 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.
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Key West Sail and Snorkel Trip from Miami

• 37 Reviews
• 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.
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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.
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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.
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Island Adventure Snorkel Kayak and Tour

• 6 Reviews
• 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.
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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.
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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.
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Key West Backcountry Schooner Eco-Tour

• 6 Reviews
• 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.
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All Inclusive Water Adventure Excursion in Key West

• 10 Reviews
• 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.
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Private Sailing Charter in Miami

• 8 Reviews
• 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.
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Swim with Whale Sharks All Inclusive Tour from Los Cabos

• 1 Review
• 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.
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Key West Sail and Snorkel Day Trip from Fort Lauderdale

• 3 Reviews
• 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.
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Sunset & Dolphin Catamaran Cruise in Panama City Beach

• Watch dolphins frolic through coastal waters on this scenic 2-hour sunset sail. Board your comfortable catamaran, listen to music, and enjoy snacks and drinks. Cruise through Grand Lagoon, passing elegant homes and St. Andrews State Park. See pods of dolphins travel together and leap above the water. Take photos and admire incredible sunset views. Don’t miss the chance to participate in games and dancing when the boat docks.
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Key West Romantic Valentine's Sunset Sail

• Celebrate Valentine’s Day in Key West on this 2-hour Champagne and Aphrodisiacs Sunset Sail! Step aboard the classic, 2-masted schooner, America 2.0, and enjoy the views as the boat sails along the beautiful turquoise green waters of Key West. Celebrate with your Valentine and enjoy a complimentary Champagne and hors d'oeuvres pairing throughout the trip. Beer, wine, soda and water also included.
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Key West Wreckers Race Aboard Schooner America 2.0

• Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern coast of Key West. When all the sailors in Key West heard there was booty to be had, they'd get in their boats and race each other out to the reef. The first one there could claim the ship's cargo. Today, we celebrate it with the firing of the canon to start the race, and all of the schooners of Key West are on their way in a one-way race to Sand Key Lighthouse! The boat that gets there first, "wins"! Highlights of the trip:- Complimentary beer, wine, champagne, soft drinks and water- A boxed lunch provided by Key West locals' favorite Harpoon Harry's Restaurant- A fast-paced and exciting race nine miles offshore into open water culminating in the rounding of the famed Sand Key Lighthouse- Iconic 360* views of Mallory Square, Fort Zachary Taylor, and Sunset Pier
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Private Sailing Trip on Biscayne Bay

• 5 Reviews
• 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.
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