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Florida Sailing trips & boat tours

Our most recommended Florida 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.

Miami: City Cruise to Millionaire's Homes & Venetian Islands

2. Miami: City Cruise to Millionaire's Homes & Venetian Islands

Relax on a sightseeing cruise through Biscayne Bay in Miami. Sail by Hibiscus Island, take in the bustling activity at the Bayside Marketplace, and relax on the shaded top deck. Board the boat from the heart of Downtown Miami or select the option with hotel pickup to enjoy a comfortable ride to the ship. Relax in luxury on a bi-level boat with open windows and a shaded deck. From downtown, you will set sail towards Star Island, where many celebrities live in their stunning mansions. Catch a glimpse of Al Capone’s house as you cruise along Biscayne Bay. Next, head to Hibiscus Island, Palm Island, Sunset Island, and Fischer Island. See the famous Venetian Islands and discover more celebrity mansions along the way. Keep an eye out for the homes of Gloria Estefan, P. Diddy, Shaquille O'Neal, Enrique Iglesias, Phil Collins, Jennifer Lopez & Alex Rodriguez, Shakira, Ricky Martin, Matt Damon, and more. Your experienced tour guide will point out all the famous homes and landmarks.  Next, cruise down to South Beach and Bayside Marketplace to truly see all that Miami has to offer. At the end of the cruise, you will dock back in Downtown Miami. Choose to add more adventure to your day with the double-decker bus combo option, where you can hop on and hop off as you like as you encounter Miami from the land.

Panama City Beach: Sunset Catamaran Cruise

3. Panama City Beach: Sunset Catamaran Cruise

Admire the sunset as you cruise around the Gulf of Mexico aboard a catamaran. Unwind with a drink as you marvel as the blue sky transforms into a spectacular light show. Check in with plenty of time, then take a 5-7 minute walk down to the dock where you will board "Footloose," your catamaran for the evening. Set sail to explore the Gulf of Mexico and admire some of the best sites Panama City Beach has to offer with the sea breeze in your hair. Listen to tropical music as you sail and enjoy a complimentary glass of wine, Sangria, cold beer, or a non-alcoholic drink. You can buy additional drinks and snacks at the fully stocked onboard bar, which takes cash or credit cards. Keep a sharp lookout for dolphins as these majestic creatures are often more active in the late afternoon. Enjoy the company of family and friends as you admire the western horizon turn every color imaginable in a breathtaking show.

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

4. 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: 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.

Madeira Beach: Pirate Adventure Cruise with Beer and Wine

6. Madeira Beach: Pirate Adventure Cruise with Beer and Wine

Take a buccaneer excursion from Madeira Beach. View the shores of Boca Ciega Bay and keep a lookout for dolphins as you sip on a wine or beer in true pirate fashion. Keep the kids happy with plenty of family-friendly activities. Embark from John's Pass in Madeira Beach and cruise through waters that are abundant with dolphins. Have some wine and beer, while the family participates in a a water gun battle, treasure hunt, pirate story, music, limbo, or face painting. Arrive back at John's Pass where you can choose to purchase a souvenir photo or to get some gear from the gift shop.

From Cocoa Beach: Sunset Catamaran Tour with Soft Drinks

7. From Cocoa Beach: Sunset Catamaran Tour with Soft Drinks

Experience the tropical Floridian coast bathed in the hazy golden hour light as you sail across the waves. Embark on a relaxing sailboat ride from Cocoa Beach and navigate over to the tranquil waters of the Intracoastal Waterway and Indian River as you sip on complimentary soft drinks. Depart from the quaint Cape Crossing Resort and Marina in Cocoa Beach aboard a stable catamaran. Unwind after a long day and keep an eye out for marine life, with the chance to see manatees and dolphins against a stunning rose-gold background. If you've ever wanted to learn how to sail, your US Coast Guard-certified captain will be happy to show you the ropes. Learn to control the steering, raise the mainsail, or lower the jib. The kids will have the time of their lives pointing out the sights displayed in the complimentary coloring book.

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.

Miami: Sunset Cruise through Biscayne Bay and South Beach

9. Miami: Sunset Cruise through Biscayne Bay and South Beach

Take a break from the bustle of Downtown Miami and watch the sunset from the water. Cruise across Biscayne Bay and admire incredible views of the city skyline. Select the option with a hop-on hop-off bus ticket to also explore Miami by bus. Relax on a luxury yacht with open windows and shaded deck, as you listen to commentary from your guide. Sail past famous islands, catch a glimpse of Al Capone’s mansion, and cruise down to South Beach. Enjoy refreshments along the way, available for purchase from the onboard bar. Head back to shore at the end of a beautiful evening.

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

10. 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 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 ecosystems in the world. See stunning elkhorn coral and impressive brain coral. Listen to explanations about marine life from the experienced captain and crew. Then, toast the end of another perfect day in paradise as you watch the sun set. Relax with complimentary soda and champagne as the sun paints the sky brilliant blues, deep yellows, and lovely shades of orange, pink, and red.

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What people are saying about Florida

Overall rating

4.2 / 5

based on 4,474 reviews

The best we have experienced on vacation. It is worth doing the tour of the skyline in the evening. And in the afternoon at sunset the tour to the houses. We can recommend it to everyone. The price is absolutely justified and nowhere cheaper.

Beautiful day on the water learning the history of surrounding buildings, islands, the port, celebrity mansions, etc… with a tour guide who was energetic and funny and knowledgeable.

+ 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