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Sailing Trips & Tours

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Our most recommended Florida Sailing Trips & Tours

Panama City Beach: Sunset Catamaran Cruise

1. 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.

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

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

Board the boat from the heart of Downtown Miami. 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: Snorkeling Trip by Boat

3. Panama City Beach: Snorkeling Trip by Boat

Enjoy a snorkeling trip by boat as you look out for dolphins and other sea creatures. Treat yourself to a complimentary drink on board as you cruise through the waters of the Gulf of Mexico. Depart into Historic Grand Lagoon for a 15-minute relaxing cruise out to the Shell Island snorkeling area. Along the way, keep your eyes out for sea animals in their natural habitat. Take in the views as the vessel drops anchor. Plunge into the waters to snorkel for seashells and to catch a glimpse of the underwater world. As well as snorkeling, treat yourself to time to relax, float, and take in the sun. Sip on a complimentary drink on board. Wade through the shallow water onto Shell Island to hunt for more shells. Before returning home, the boat will ride out further into the Gulf of Mexico to search for more dolphins and sight-see along the way.

Miami: 1.5-Hour Evening Cruise on Biscayne Bay

4. Miami: 1.5-Hour Evening Cruise on Biscayne Bay

Enjoy the waters of Miami and the city lights from Biscayne Bay aboard a cruise boat. Watch the city come to life at night when the sun goes down and the city lights come on. Thousands of lights illuminate the incredible high-rise buildings and city skyline around the bay. During your tour, sip on your beverage of choice which is purchasable from the cash bar. Take in sights such as Millionaire's Row, Bayside, South Beach, and the Miami River. Finish your tour with a moon-watching activity and admire the moon's reflection on the water below you. Enhance your experience with an optional hour-long city tour on a double-decker bus before going on the cruise.

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: Sunset Sailing Trip with Open Bar, Food and Music

6. 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.

Miami: Sunset Cruise through Biscayne Bay and South Beach

7. 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. Enjoy refreshments along the way, available for purchase from the onboard bar. 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. Head back to shore at the end of a beautiful evening.

Miami: Parasailing Experience in Biscayne Bay

8. Miami: Parasailing Experience in Biscayne Bay

Discover Miami from a unique perspective: soaring high on a parasail. Glide over Biscayne Bay with unparalleled views of Miami's stunning landscape as your parasail boat smoothly pulls you along. Dip into the refreshing waters right before landing back on the back of the boat. Arrive at your departure location where you will be introduced to the captain and mate. Departing from the dock on the parasail boat, the mate will go over the safety instructions and get everyone geared up. After a five to 10-minute boat ride into the bay, the captain will open up the parachute and call the first flyers up. Take off from the boat and enjoy a scenic ride over Miami. Right before landing back on the boat, enjoy a little dip in the water to cool down from the hot Miami sun. The other flyers will get a chance to enjoy the same experience before you ride back to the departure point. 

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.

Cocoa Beach: Dolphin Watching and Sightseeing Catamaran Sail

10. Cocoa Beach: Dolphin Watching and Sightseeing Catamaran Sail

Sail along the tranquil Indian River Lagoon and the renowned Intracoastal Waterway on an unforgettable sightseeing boat trip from Cocoa Beach. Enjoy the once-in-a-lifetime opportunity to see dolphins, manatees, and sea birds in their natural habitat, with stops along the way. Join your captain to learn about the Indian River Lagoon Estuary, one of North America's most diverse ecosystems. Besides dolphins, look out for splashing fish, soaring ospreys, gorgeous bald eagles, and enormous manatees. Bring the whole family along on this fun and informative activity. Live out your sailing fantasies by controlling the steering, raising the mainsail, or lowering the jib. Meanwhile, the kids will love gazing at a tiny coloring book of nearby sights that they may keep. Take a break from the beach and head deep into the ocean while on your Cocoa Beach holiday.

Frequently asked questions about Florida Sailing Trips & Tours

What are other things to do than Sailing Trips & Tours that are worth visiting in Florida?

The other unmissable things to do in Florida are:

Other Sightseeing Options in Florida

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What people are saying about Florida

Overall rating

4.2 / 5

based on 4,474 reviews

An incredible tour in the bay of Miami, view of Miami Skyline, the islands, and Miami River... We even saw dolphins in the bay !!! The boat was very spacious and modern and the Capitaine Charlie was very nice with a lot of explanations! A great experience that I recommend to all those who want to mark their stay! Thanks again to our captain Charlie!

Our activity leader was energetic and added comedic overtones when providing details on our sightseeing.The music was in sync with what we were observing. While I am not bilingual, I appreciated that she was able to translate in both English and Spanish. Overall, excellent experience!

Captain Russ, Mario and Bradley did a fantastic job! They were very knowledgeable and personable! We highly recommend this awesome adventure!

I really enjoyed this activity. The views, music and tour were very nice and the drinks were good.

Michael was the best! Considering doing this again before my trip is over best $ I’ve spent here