Florida Keys
Sailing Trips & Tours

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Our most recommended Florida Keys Sailing Trips & Tours

Key West: 2-Hour Sunset Sail on Schooner America 2.0

1. Key West: 2-Hour Sunset Sail on Schooner America 2.0

Take in the vibrant colors of Key West's fabulous sunset as you glide through the waters on one of the finest boats in the Key West Schooner Fleet. Watch the sun fade into the horizon and the stars emerge into the deep blue sky. America 2.0 features teak decks, mahogany-trimmings, and 3,600 square feet of canvas! Sit back and relax while she plies effortlessly through the crystal-clear waters off Key West, heading towards the horizon for the quintessential Florida sunset experience! Some of the sights on this sailing adventure include a view of Fort Zachary Taylor from the water, and views of the famed Sand Key Reef, Mallory Square, and Sunset Pier. Keep your eyes peeled for wildlife such as dolphins, sea turtles, and water birds – and for the famous Key West "Green Flash" at sunset. Bring your family or friends and join the courteous and professional crew for this sunset sail that completes the Key West experience in comfort and elegance.

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Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas

2. Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas

Hop onboard your catamaran for the morning then set sail onto Key West’s glistening turquoise waters towards the third longest reef in the world. During the cruise, soak up epic views of the coastline and snack on a delicious, light breakfast accompanied by mimosas. Upon arrival at the snorkel site, get kitted out with all the necessary gear and listen to a safety briefing. Afterwards, make a splash as you jump into the refreshing, crystal clear water. Follow your instructor as you navigate this impressive coral reef and snorkel in search of colorful marine life. During the experience, enjoy the opportunity to see some of Key West’s 110 species of coral and 500 species of tropical fish. At the end of an epic adventure, relax on deck, grab a beer, and soak up the last of the coastal views as you sail back to port.

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Key West: Sunset Cruise with Buffet Dinner and Open Bar

3. Key West: Sunset Cruise with Buffet Dinner and Open Bar

Climb aboard "The Party Cat" for a wonderful 2-hour cruise around the harbor.   Enjoy a freshly prepared tropical food buffet in an enclosed air-conditioned dining room. Choose from dinner options such as roast pulled pork in mojo sauce, deep fried sweet plantains, black beans and rice, marinated grilled chicken, fried fish, mixed vegetables, mashed potatoes, pasta with mini shrimp and Cuban bread and butter. Sip on your choice of tipple — margaritas, rum runners, champagne, beer, wine or spirits. After dinner, stroll upstairs to the upper deck for live music. Dance the night away or simply listen to the beat as you watch the sun set over the horizon into the Gulf of Mexico. Witness the beautiful display of colors across the night sky.

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Key West: 3-Hour Snorkeling Adventure

4. Key West: 3-Hour Snorkeling Adventure

Spend an enjoyable 3 hours in the sunshine and crystal-clear waters of the Florida Keys and snorkeling along Key West’s coral reef. You’ll experience the ultimate in snorkeling and sailing comfort on a state-of-the-art catamaran, featuring: • A stairway to the sea • Large sundeck • Shaded lounge area • Fresh water rinse • Restrooms • Top-of-the-line sanitized snorkeling gear • Professional instruction by Fury’s friendly crew Before snorkeling, the crew will be on-hand to assist and instruct you. Once you descend the stairway to the sea, you’ll discover the wonders of the underwater world. Marvel at the pristine coral reef and its abundance of marine life, including tropical species found nowhere else on earth. The morning snorkeling tour includes unlimited water and sodas and complimentary beer, wine, and mimosas after snorkeling. The afternoon Reef & Ritas snorkeling tour is a great opportunity to enjoy a luxurious catamaran sail to the only living coral reef in North America. The afternoon sun is warm and bright, making it a great time to relax on the catamaran and enjoy the temperate ocean waters. The ocean currents and wind direction are often different than in the morning, so if you’ve taken a morning snorkeling trip in the past, chances are you’ll go to a different reef location in the afternoon.

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Key West Dolphin Watch and Snorkel Eco Tour

5. Key West Dolphin Watch and Snorkel Eco Tour

Climb aboard a fast catamaran for an aquatic journey of a lifetime, and observe the grace and beauty of resident Key West dolphins in the shimmering turquoise waters of the Gulf of Mexico. Look for bottlenose dolphins as they swim, play, feed and do what comes naturally. Then, head to the Key West wildlife refuge to snorkel in the shallow backcountry waters. Relax in the knowledge that your tour is provided by the only company in the Florida Keys with the prestigious “Dolphin SMART” certification, a national program that protects and promotes the responsible observance of dolphins. The program was put together by conservation agencies, including the National Marine Sanctuary of the National Oceanic and Atmospheric Administration, the National Marine Fisheries Service, the Dolphin Ecology Project and the Whale and Dolphin Conservation Society. Begin your ride back to the dock, and enjoy a complimentary cold beer and chilled wine, whether you choose the morning or afternoon option. Opt for the sunset tour and experience the world famous Key West sunset as a bonus.

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Key West: Glass-Bottom Boat Sunset Cruise and Reef Tour

6. Key West: Glass-Bottom Boat Sunset Cruise and Reef Tour

Climb aboard a glass-bottom boat and cruise the tropical waters of Key West with a warm ocean breeze as your backdrop. Get dramatic underwater vistas before the sun sets, and see a wide variety of fish and other sea creatures. Take advantage of the glass-bottom boat's outdoor deck with seating and air-conditioned enclosed viewing area. Benefit from facilities that include restrooms and a snack bar. The catamaran’s twin hull design allows for maximum stability and much less rocking motion than traditional V-hull boats, allowing for maximum viewing with minimum stress to the delicate reef. Marvel at North America’s only living coral reef and one of the most biologically diverse marine eco-systems in the world. See stunning elkhorn coral and impressive brain coral. Sturdy in appearance, yet fragile and vulnerable, these magnificent coral species stand sentry for more than 300 species of fish. Listen to explanations about the marine life from the experienced captain and crew as you get a “Window to the Reef” via the boat's special glass. Then, toast the end of another perfect day in paradise as you watch the sun slowly disappear beyond the horizon. Relax with complimentary soda and champagne, and snuggle up with that special someone as the sun paints the sky brilliant blues, deep yellows, and lovely shades of orange, pink and red.

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Key West: 3-Hour Coral Reef Snorkeling

7. Key West: 3-Hour Coral Reef Snorkeling

Spend your morning or afternoon snorkeling in warm tropical seas surrounded by colorful fish. Enjoy expert instruction and learn about the reef’s marine wildlife from the professional crew. Your captain will select the exact location based on water and wind conditions, to give you best snorkeling in Key West. Dive into the calm waters, and see how many species of fish and coral you can find. Afterwards, grab a complimentary drink and lay on the sun deck, or cool off in the shade as you sail back to Key West. Feel the breeze in your hair and watch for dolphins playing in the ship’s wake.

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Key West: 2-Hour Sunset Sail with Live Music

8. Key West: 2-Hour Sunset Sail with Live Music

Set sail on a breathtaking sunset cruise aboard a spacious catamaran. Admire views of the Historic Seaport, pass jugglers and entertainers at the Mallory Square Sunset Celebration, and gaze at Fort Zachary Taylor. Enjoy unlimited drinks and appetizers on board, as well as live musical entertainment. Sail past the landmarks of Key West, as your captain positions the ship to maximize your view of the sunset. Savor a fantastic evening on the water.

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Key West Double Dip: 2-Stop Reef Snorkeling Trip

9. Key West Double Dip: 2-Stop Reef Snorkeling Trip

The only thing better than snorkeling in Key West is doing it twice! Climb aboard the fast Fury catamaran and head out to Key West’s underwater marvels. During this 3-hour trip you’ll have the opportunity to explore the reef at 2 different locations. The Reef Express is a 57-foot power catamaran built for speed and comfort. It’s the quickest way to get to the reef, so you spend less time traveling and more time snorkeling. Once you reach the reef, you’ll be provided top-of-the-line snorkeling gear including a snorkel, mask, fins and a snorkeling vest. You’ll also get some professional tips and guidance on how to snorkel to better enjoy your experience. After meeting some of the most popular residents – the colorful marine species that inhabit the reef – you'll be transported to another ideal location on the reef for more snorkeling. Double Dip provides approximately 1.5-hours of Key West snorkeling during a 3-hour adventure. If you select the Double Dip Sunset Combo trip, after experiencing the finest Key West snorkeling, the Reef Express will head out to sea to find the perfect place to watch a dramatic sunset. Raise your glass of complimentary Champagne as you toast another fun-filled day in the paradise that is Key West.

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Key West: Rum and Reggae Afternoon Snorkel and Sunset

10. Key West: Rum and Reggae Afternoon Snorkel and Sunset

Enjoy 2 exciting activities in 1 trip as you snorkel North America’s only living reef system from a spacious catamaran, enjoying the rhythmic sounds of reggae music in tropical waters. Then, watch the sunset over the horizon! Climb aboard the state-of-the-art catamaran from the most luxurious fleet in the Florida Keys. Upon arrival at the reef, get assistance and instructions from the friendly crew before you descend “the stairway to the sea.” Discover the wonders of the aquatic environment and its pristine coral reefs, and snorkel among an abundance of marine life, including tropical species found nowhere else on earth. Upon completion of your snorkeling adventure, enjoy some complimentary rum punch, a signature tropical beverage, beer, wine and champagne. Then, leave your worries behind as you sail off into Key West’s famous sunset. Feel the warm ocean breeze as you watch a magnificent sunset. Toast the end of another perfect day in paradise as you see the sun slowly disappear beyond the horizon.

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Other Sightseeing Options in Florida Keys

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What people are saying about Florida Keys

Thank you! Great trip!! I’ve experienced panic attacks on my other snorkeling trips. Lisa helped understand why and I was able to snorkel!! Her assistant Cat was also excellent! Thank you so much!!

Bill, Alex, and Neko are great guides. They made the boat ride to the reef fun. The reef was an excellent location with plenty of fish that get right up to your face. I would definitely recommend.

Great trip on a calm lake with a very large and generous selection of drinks and various snacks. The sunset at Key West is an experience.

I was very impressed with the quality of the food. The DJ/Performer was excellent. Good time. Thank you.

As advertised!. Great hard working crew on the Sunset Cruise on 12-29-21. Highly recommended.