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Key West Sailing trips & boat tours

Our most recommended Key West Sailing trips & boat 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.

Key West: Dolphin Watching and Snorkeling Eco Cruise Tour

2. 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

3. 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: 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: 2-Hour Sunset Sail with Live Music

5. 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: 3-Hour Coral Reef Snorkeling

6. 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: 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: Dolphin Watching & Snorkeling

8. 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 Island Adventure Eco Tour

9. Key West Island Adventure Eco Tour

Experience the laid-back vibe of Key West on an island adventure that can end with a stunning sunset, if option booked. Board a custom-built, spacious catamaran specially designed for this trip and with a unique construction that allows you to get in and out of the shallow waters smoothly and quickly. Get a complimentary snack or light breakfast, depending on your time of departure, and then head towards a remote natural sandbar through the narrow passages of the lake. Marvel at the lush mangroves surrounding you as you follow a route that only the locals know about. Wind your way through the tropical keys, looking for playful dolphins and curious sea turtles. Each trip is different, just like the locals. Once you reach your destination, get all the gear necessary for snorkeling (mask, fins, snorkel and a float if you wish), and then discover the underwater world in the calm, shallow and warm waters. Get up-close views of the colorful sea life that live amongst the beautiful coral heads. Next, indulge in a delicious buffet lunch as you head to a remote natural sandbar for a day of fun in the sun. Upon arrival, sip a cool drink and sink your toes in the warm water, or grab a kayak to experience Key West from a different perspective. The crew will guide you on the best way to kayak, and share their knowledge of the area. Choose the sunset option and you will head to the best spot to view a glorious Key West sunset at the end of the day. Toast nature’s dazzling display of colors with a glass of chilled champagne before heading back to the dock for the end of the tour services.

Key West: 3-Hour Afternoon Reef Snorkel with Drinks

10. 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.

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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!