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Key WestSailing trips & boat tours

Our most recommended Key West Sailing trips & boat tours

Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

1. Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

Enjoy a dolphin-watching cruise in Key West. Snorkel in the Key West Wildlife Refuge, see playful bottlenose dolphins, and enjoy a cold beer or wine as you cruise. Climb aboard a fast catamaran and head out into the Gulf. As you cruise, see the grace and beauty of the resident Key West dolphins in the shimmering turquoise waters of the Gulf of Mexico. Look for bottlenose dolphins as they swim, play, and feed. Then, head to the Key West Wildlife Refuge to snorkel in the shallow backcountry waters. Relax in the knowledge that your tour has the prestigious “Dolphin SMART” certification, a national program created by conservation agencies, that protects and promotes the responsible observance of dolphins. Begin your ride back to the dock, and enjoy a complimentary cold beer and chilled wine. Opt for the sunset tour and experience the world-famous Key West sunset as a bonus.

Key West: Sunset Sailing Trip with Open Bar, Food and Music

2. Key West: Sunset Sailing Trip with Open Bar, Food and Music

Join a sailing experience to get you closer to the sunset than ever before. Set sail from the historic sea port of Key West and head straight out to sea for a cruise with unobstructed views of the sunset on the horizon. During the cruise, enjoy an unlimited open bar, with a wide variety of drinks on offer including rum runners, Champagne, margaritas, and draft beer. Taste a selection of finger foods, ranging from Swedish meatballs, veggie treats, cheese and crackers, pita and hummus, and meat and veggie platters. You will be sailing on one of Key West's newest sailing catamarans, the Sandie Cat. This vessel has capacity for up to 149 passengers across 3 decks, so there will always be plenty of room onboard. Grab a drink, head to the upper deck, and dance to live music as you watch the sun go down. The captain and crew will even let you help raise the sails and you can ask to have a picture taken driving the boat.

Key West: Dolphin Watching & Snorkeling

3. Key West: Dolphin Watching & Snorkeling

Climb aboard the Sunset One dolphin boat, sit back and listen to your tour guide explain where you are and where you are heading. Get ready to watch dolphins frolic in their natural playground.  Marvel as the dolphin swim closer to the boat so you can get a better view. Head out to the small islands within the boundaries of the Key West National Wildlife Refuge. Soak in this beautiful little chain of islands and jump into the gorgeous reef, perfect for snorkeling.  See fish up close and maybe some turtles. Climb back aboard and settle yourself in for the ride back to the dock with an ice cold draft beer. Watch the beautiful panoramic sunset over the crystal clear turquoise waters.

Key West: 3-Hour Coral Reef Snorkeling

4. 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.

Key West: Sunset Cruise with Buffet Dinner and Open Bar

5. 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.

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

6. 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.

Key West: 2-Hour Sunset Sail with Live Music

7. 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.

Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas

8. 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.

Key West: Sunset Party Cruise by Catamaran

9. Key West: Sunset Party Cruise by Catamaran

Climb aboard a party catamaran and sail across the ocean waves on a sunset cruise from Key West. Get ready to dance the night away and cause a commotion on the ocean! Enjoy free hot an cold snacks, including a fresh vegetable platter with hummus and a smoked fish dip with pita chips. Listen to live music as you sip margaritas and wine. Quench your thirst with a cold beer and leave your worries behind as you sail into the sunset. Relax aboard the spacious state-of-the-art catamaran as you cruise the tropical waters. Feel the warm ocean breeze on your face and toast the night with a glass of champagne. Dance to the sounds of your favorite musicians as the sun slowly sets across the sea.

Do It All Watersports With Parasailing

10. Do It All Watersports With Parasailing

Climb aboard the 'Party Cat', a 65-foot motorized double decker catamaran, and meet the crew and Captain. Recieve instructions on how your trip will go and pick a fun name for your group. Enjoy a short boat ride out to the Playground, where all the activities are set up ready for your day of fun. Schedule your parasailing time then climb aboard some of the newest Jet Skis in Key West and play around on them. Swim over to a sunken ship to enjoy some fun snorkeling. Have a bounce on the water trampoline then hold on tight as the SkiBoats take you for a fun filled Banana Boat ride. You can climb to the top of a floating IceBerg then jump off into the cool crystal blue waters, or paddle around the area in state of the art kayaks and paddle boards. Try your luck at waterskiing and knee boarding. Re-energise as you enjoy a grilled lunch in the air-conditioned, fully enclosed lower cabin of the boat. Once you are all worn out, sit back, relax, and enjoy a cold draft beer as you make your way back to shore.

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Frequently asked questions about Key West Sailing trips & boat tours

What are other things to do than Sailing trips & boat tours that are worth visiting in Key West?

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Other Sightseeing Options in Key West

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What people are saying about Key West

Overall rating

3.9 / 5

based on 307 reviews

+ Many dolphins close to boat + Very nice snorkeling area for beginners (clear water, shallow, no current) + complementary drinks

One of the best experiences in Key West. Good food, good drinks, good music, great fun!

Wonderful tour out to the sea and see the stunning coral reef

Great guides, great experience. My kids loved it, so did I.

The staff is so personable and fun. Always a good time!