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Key West Sailing trips & boat tours

Our most recommended Key West Sailing trips & boat tours

Key West: 3-Hour Coral Reef Snorkeling

1. 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 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 and Snorkeling Eco Cruise Tour

3. 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 Cruise with Buffet Dinner and Open Bar

4. 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: Dolphin Watching & Snorkeling

5. 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 Afternoon Reef Snorkel with Drinks

6. Key West: 3-Hour Afternoon Reef Snorkel with Drinks

Climb aboard “the Sandy Cat”, Key West’s newest catamaran and settle in for a lovely sailing trip out to the reef. Once the Cat is moored, you can jump out or slide into the water and swim over to the reef.   The coral reefs of Key West lie about 7 meters offshore, and are the third largest barrier reef system of the world. There’s nowhere else in North America where you can view such an abundance of wildlife in just one location.   After about 1 hour of snorkeling and swimming, climb back on board for a lazy, relaxing sail back to the port with a nice cold draft beer in your hand. For those who want something a bit stronger, a complete cash bar will be available on board.

Key West: Reef Snorkel Morning Tour with Breakfast & Mimosas

7. 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: 3-Hour Snorkeling Adventure

8. 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.

Key West: All Inclusive Watersports Adventure Tour

9. Key West: All Inclusive Watersports Adventure Tour

Climb aboard a state-of-the-art catamaran and sail to the only living coral reef in North America. Enjoy a delicious breakfast of egg and cheese sandwiches, fresh fruit, granola, and assorted pastries and water, soda and lemonade served throughout the day. Sunbathe and relax on the spacious deck as you cross the Gulf of Mexico for an all-you-can-eat picnic buffet, with sandwiches, fried chicken, veggie and hummus wraps, coleslaw, pasta salad, and cookies. On arrival, snorkel for 1 hour and see angelfish, parrotfish, blue tangs, and other species. Then, cross to the Gulf of Mexico for an all-you-can-eat picnic buffet lunch. Dock at a floating platform and spend the afternoon on jet skis, parasailing, banana boating, and playing aquatic games such as the Action Climbing Tower and Aqua Slide. Cool down with complimentary beer and wine before you sail back to Key West.

Key West: Sunset Party Cruise by Catamaran

10. 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.

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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?

The other unmissable things to do in Key West are:

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!