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Sailing Trips & Tours

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Our most recommended Florida Sailing Trips & Tours

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

1. 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: Sunset Catamaran Cruise

2. 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: 1.5-Hour Evening Cruise on Biscayne Bay

3. 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.

Panama City Beach: Snorkeling Trip by Boat

4. 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.

Shell Island: Water Park and Dolphin Watching Boat Trip

5. Shell Island: Water Park and Dolphin Watching Boat Trip

Embark on a boat trip from Panama City Beach to Shell Island, including a complimentary drink and a variety of water activities to make your day memorable. Have fun at the inflatable water park or try out kayaking or snorkeling. End your day sailing into the Gulf of Mexico for dolphin sightseeing.  Your day begins with a scenic trip through Grand Lagoon and over to Shell Island. Once at Shell Island, enjoy an inflatable water park, paddleboards, kayaks, and snorkeling. Have a go on trampolines, a water see-saw called the “rockit,” and other inflatables. If you’re looking for something a little more slow-paced, explore the waters on a kayak, take a paddleboard ride, or give snorkeling a try. Get plenty of time to take in all of the natural beauty that Shell Island has to offer. If just hanging out is your plan, relax and listen to music on the boat or in one of the two sunning nets located at the front of the boat while you sip on a refreshing beverage. All activities and inflatables are all-inclusive with unlimited use during your trip. The last portion of the trip will be spent sightseeing and dolphin watching before making a round-trip return to Panama City Beach.

Panama City Beach: Dolphin Watching Trip by Catamaran

6. 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.

Crystal River Small Group Swim with Manatee Tour

7. Crystal River Small Group Swim with Manatee Tour

Swim with manatees in the spring-fed King’s Bay Wildlife Refuge in Crystal River, home to the world’s largest population of the endangered creatures during the winter. Encounter these gentle giants in their natural habitat. Benefit from the services of a Coast Guard certified captain and in-water educator and photographer. Learn about the animals in a classroom-type setting and get tips to make the most of your day. Hear about passive interaction to make sure that the animals enjoy the experience just as much as you do! Then, suit up and board a covered pontoon boat to immerse yourself in the manatees' world. Be treated like royalty aboard the boat and see the wildlife refuge in style. Return to the facility at the end of your adventure and visit the one-of-a-kind gift shop! Hear about other local attractions and restaurants, and get answers to any questions you may have before you depart.

Key West: Sunset Cruise with Buffet Dinner and Open Bar

8. 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

9. 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: Parasailing Experience in Biscayne Bay

10. 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. 

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

It was an experience that we were so glad we booked!! We knew going in that wildlife doesn’t always want to be seen but we were very fortunate that our captain found us two gators not to mention the birds, deer, eagle, turkeys…. But the ride alone would have been great too! We booked an hour tour and it was the perfect amount of time on the water! A very fun and fast speed ride!

Did parasailing for the first time to start off my birthday celebration! It was amazing!! Beautiful views, thrilling, and a super fun/safe captain! Would definitely do it again and recommend to all

Landon and Pierre were excellent. Their patience, confidence and great enegery helped me relax enough to enjoy myself!!

We enjoyed the ride very much. What a pleasant experience to be out in the speed boat. I would highly recommend it.

So beautiful, relaxing, and breathtaking all at once!!