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Florida Sailing trips & boat tours

Our most recommended Florida Sailing trips & boat tours

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

1. 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.

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

2. 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.

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: Dolphin Watching and Snorkeling Eco Cruise Tour

4. 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

5. 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

6. 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.

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.

Madeira Beach: Pirate Adventure Cruise with Beer and Wine

8. 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.

Panama City Beach: Dolphin Watching Trip by Catamaran

9. Panama City Beach: Dolphin Watching Trip by Catamaran

Head out to sea to meet the resident Panama City Beach dolphins. Enjoy informative commentary from your captain and crew, and sip a complimentary drink as you go. Board the “Footloose” Catamaran and head out into shimmering waters of the Gulf of Mexico near Shell Island. Partake in a beer, wine, or soft drink as you head out from the dock. Watch the dolphins as they swim, play, and feed in their natural habitat. Learn all about these beautiful creatures with informative commentary from your captain and crew. Take advantage of an onboard bar during your trip. Keep your eyes out for encounters with the bottlenose dolphins as you voyage through the turquoise waters.

Key West: 2-Hour Sunset Sail with Live Music

10. 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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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