Orlando
Sailing Trips & Tours

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Our most recommended Orlando Sailing Trips & Tours

Orlando: Boggy Creek Airboat Ride with Options

1. Orlando: Boggy Creek Airboat Ride with Options

The Central Florida Everglades are natural wonders, best explored with locals who know their backwaters. The beautiful landscape and expert guidance of your captain will make this tour a trip that you'll never forget. Guests on the Scenic Nature Tour explore narrow water trails engulfed in the brush of the Central Florida Everglades. On this tour you'll stop periodically, hoping to spot Florida's state reptile, the American Alligator, in its natural setting. Witness rare and endangered birds swooping effortlessly through the skies as the sunshine warms your body and the wind whips through your hair. Other wildlife abounds throughout the trip. This tour is perfect for groups and families looking to explore and learn about the unexpected side of Central Florida. A longer trip on a Detailed Nature Tour of 1-hour increases the number of encounters with Florida's wildlife, especially the American Alligator, which can reach up to 15 feet in length and 1,000 pounds. You'll experience nature right alongside turtles, bald eagles, blue herons, deer, and a wide variety of waterfowl in their natural environment, not in captivity. Be sure to also check out the Gem Mining Station. You will be able to purchase buckets filled with treasures that are native to Florida and take them to the mining station. While mining, you will discover various gems, alligator teeth, shark teeth, rocks, and other treasures. There will be an additional charge for gem mining bags or buckets. A restaurant with indoor or patio seating is available, where you can dine before or after your tour (at your own expense).

From Orlando: Clearwater Beach Pirate Cruise with Lunch

2. From Orlando: Clearwater Beach Pirate Cruise with Lunch

Start the day with pickup from Orlando in a luxury vehicle, then head towards Clearwater Beach. Hop onboard the Pirate’s Ransom and greet your friendly crew. Learn how Florida was a well-known pirate hangout in the 17th and 18th centuries, and hear stories of Captain Kidd and the infamous Blackbeard. Set sail onto the glistening waters of the Gulf of Mexico and lookout for dolphins swimming in their natural habitat. As you cruise, enjoy 2 hours of family fun including a treasure hunt, face painting, water guns, story-telling, and dancing. During the day, enjoy free time to sunbathe on the white sands of Clearwater Beach or go for a swim. A tasty lunch at a local beachside restaurant is included. At the end of a truly epic adventure, relax on the return journey to Orlando.

From Orlando: Clearwater Beach with Lunch Day Trip

3. From Orlando: Clearwater Beach with Lunch Day Trip

Escape the crowds and queues with this trip to Clearwater, where you can have fun in the sun. Journey to the white sands and warm waters of Florida's West Coast. Enjoy an amazing lunch while feeling the cool breeze and taking in the beautiful scenery around you. Let the sugary sands fall between your toes as you take a stroll down this gorgeous beach. Upgrade your tour to include a number of optional activities: Dolphin Encounter Boat Tour: Embark on a 2-hour boat cruise from Clearwater Bay into the clear blue waters of the Gulf of Mexico. Sit back and relax while your captain highlights some fascinating facts about the Gulf Coast, celebrity Mansions, and the dolphins playing.  Sea Screamer Ride: Climb aboard the Sea Screamer, the world's largest speedboat! Experience the dual twin-turbocharged diesel engines, as the 72' long Sea Screamer gives you a thrill ride you'll never forget.  Pirate Cruise: Sail away with Captain Memo’s Original Pirate Cruise to a world complete with briny buccaneers and seafaring seadogs. Let the tropical island tunes guide your journey through the calm waters of the picturesque Gulf of Mexico. Deep Sea Fishing: Florida has featured in its fair share of fishing folklore over the years and tall tales abound. The sport fishing is indeed excellent so here’s your chance to head out and do battle.  Aquarium: Go beyond a typical aquarium experience and immerse yourself in the world of marine life rescue at Clearwater Marine Aquarium. This unique, nonprofit rescue facility is dedicated to the rehabilitation and release of marine animals.

From Orlando: Day Trip to Clearwater Beach with Options

4. From Orlando: Day Trip to Clearwater Beach with Options

Sit back, relax, and let your driver fight the highway traffic from Central Florida to the Gulf of Mexico. Enjoy convenient and complimentary pickup and drop-off from many hotels in Orlando to take the worry out of your day. Find out why Clearwater Beach is one of America’s beaches. Choose between the following tour options offering something for all the family: • Clearwater Beach Day Trip with Marine Aquarium Admission: Meet Winter, the dolphin from the blockbuster movie “Dolphin Tale,” at Clearwater Marine Aquarium. Watch dolphins frolic from the underwater viewing platforms, and learn more about their incredible skills and natural habitats. • Clearwater Beach Day Trip with Pirate Cruise: Set sail aboard Captain Memo's Pirate Cruise for an afternoon of adventure in the Gulf of Mexico. Get lost in the antics of treasure hunts, face painting, water gun games, stories, and dancing. During the cruise, enjoy complimentary beer, wine, and soft drinks. • Clearwater Beach Day Trip with Dolphin Encounter Boat: Venture from Orlando to Clearwater Beach then board the Dolphin Encounter boat for a ride into the Gulf of Mexico. See dolphins in their natural habitat, and watch them play as you enjoy the sun and sea. • Clearwater Beach Day Trip with Deep-Sea Fishing: Explore the beach in the morning then have the opportunity to catch and keep a variety of fish in deep-sea conditions. Receive all the necessary fishing equipment, including a fishing license. This excursion goes 10 miles (16 kilometers) into the gulf, which takes 45 minutes each way. • Clearwater Beach Day Trip with Lunch: This transportation-only trip will whisk you away from the theme parks of Orlando to the powder-white sands of Clearwater Beach. Enjoy a day to do as you please with an included lunch voucher. Kayak in crystal clear water, or walk the promenade of the resort’s fishing pier. • Clearwater Beach Day Trip and Sea Screamer Boat Ride: Journey out to Clearwater Beach for a thrilling ride on the Sea Screamer – the largest speedboat on the U.S. East Coast. Witness wild dolphins jumping through the wakes created by the large boat. • Clearwater Beach Day Trip with Express Bus Transportation: Choose this express transportation option to avoid all the pickup stops and go directly to the beach. Once there, lounge on the white sand, jump through the turquoise waters, explore the pier, get some fresh-caught fish for lunch, and more.

From Orlando: Clearwater Beach Speedboat Tour with Lunch

5. From Orlando: Clearwater Beach Speedboat Tour with Lunch

Hop aboard the world's largest speedboat, the Sea Screamer, and discover magnificent Clearwater Beach. With its dual twin turbocharged engines, the Sea Screamer is the perfect way to roar along the Clearwater coastline and invite the dolphins to leap into its foaming trail as it hits a top speed of 35mph. After your exhilarating maritime adventure, you still have the fun and enjoyment of America’s Beach to revel in for the rest of the day. With its small waves, this beach is great for families, and the long Beach Walk promenade offers an enticing array of shops, restaurants, and bars. Hit Pier 60 for iconic Clearwater Beach photographs and enjoy lunch at one of the many beachfront diners, where you can enjoy classic local fare.

Orlando: Private Sunset Sailing Trip on Lake Fairview

6. Orlando: Private Sunset Sailing Trip on Lake Fairview

Set sail on a private boat tour of Lake Fairview. Admire the sunset as you learn how to sail. Meet your tour guide and sailing instructor at the boat ramp. Put on your life jacket then, climb about the 25ft vessel and set sail. Be as involved as you like, learn the fundamental principles of sailing or sit back and relax on a sunset cruise. Enjoy an immersive experience and become part of the crew. Help trim the sail and take the helm. Follow your instructor's commands to raise and lower the sails, steer, and turn the boat. Then, relax in the comfortable cockpit as you admire the sunset reflected in the water.

From Orlando: Miami Boat Cruise & Walking Tour

7. From Orlando: Miami Boat Cruise & Walking Tour

Depart from Orlando in the early morning and enjoy a continental breakfast snack to enjoy en-route down to the South Florida hotspot of Miami, where your first stop is the waterfront Bayside Marketplace Mall.  Once there you will board the boat. Sit back and relax for an unforgettable fully-narrated bilingual sightseeing cruise along scenic Biscayne Bay. See Miami's spectacular coastal sites including the beautiful downtown Miami skyline, the Port of Miami, Fisher Island, Miami Beach and "Millionaire's Row" - the homes of the rich and famous. Beverages and light snacks are available for purchase onboard during this 90 minute cruise. In the later afternoon travel over to the City of South Beach - this is the unique area you often see in movies with the pastel colored buildings and stunning white sandy beach.  This tour gives you free time to enjoy the beach, shop Lincoln Avenue, enjoy a restaurant on Ocean Avenue or just people watch.  This is an awesome way to see the sights of Miami. This great tour of two different city areas is not to be missed.

Orlando: Sailing Tour with Certified Sailing Instructor

8. Orlando: Sailing Tour with Certified Sailing Instructor

Set out on a 2-Hour sailing experience in Central Florida. Learn how to sail with a certified sailing instructor, and enjoy drinks and snacks along the way. Meet your tour guide and sailing instructor at the boat ramp. Put on your life jacket and climb aboard the 25-foot MacGregor sailboat. Be as involved as you like — learn the fundamentals of sailing or sit back and relax on a sunset cruise. Enjoy an immersive experience and become part of the crew. Help trim the sail and take the helm. Follow your instructor's commands to raise and lower the sails, steer, and turn the boat.

From Orlando: Miami Day Trip with Upgrade Options

9. From Orlando: Miami Day Trip with Upgrade Options

Take a day to experience the energetic and vibrant city of Miami. Discover the different areas of the city while shopping, enjoying the atmosphere, or simply relaxing. Leave from Orlando early in the morning to experience a whole day of fun. On the way, receive a continental-style breakfast bag to get energized for the day. Choose from the following tour options: • Full-Day Hop-on-Hop-off City Tour: See all that Miami has to offer on two routes of the city. Enjoy live commentary on the tour with plenty of time to explore your choice of stops. Discover Miami's highlights as you hop on and off at your own leisure. • Miami Tour with Celebrity Homes Cruise Around Star Island: See Miami's magnificent coastal sites — including the Miami skyline and the homes of Star Island — on a fully narrated cruise. After, enjoy plenty of time to shop in the Bayside Marketplace Mall and relax on South Beach as well. • Day Tour of Miami: Experience and explore the Bayside Marketplace and South Beach area of one of the most upbeat cities on the East Coast of the United States. Choose this option to have the most free time to explore on your own. • Everglades Adventure and Star Island Cruise: After a brief stop at Bayside Marketplace, set off on an adventure in the Florida Everglades with an airboat ride and animal handling show. Then, head back to Bayside Marketplace for a bit of free time before boarding the Island Queen for a fully narrated cruise around Star Island. Finally, visit South Beach briefly to soak in a little of the atmosphere. After a fun-filled day in Miami, your driver will take you back to Orlando where the tours will end.

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What people are saying about Orlando

Overall rating

4.2 / 5

based on 14 reviews

We had a great time here for the day. We booked the complete package which included 1 hour airboat, gem mining and lunch. It's a really cute spot next to a park area with picnic tables. As we arrived there were 2 buses of students loading back up so I'm glad we had booked a later tour. We went on the 2:30pm airboat with a few other people. It was amazing and we saw a moma gater with her babies and even a bald eagle nesting. Very informative and 60mins goes by really fast. We then went and had lunch at onsite restaurant. We were offered a chose of chicken sandwich or hamburgers or pulledpork. We both had the bbq pulled pork sandwiches that were delicious!!..they are served plain and you choose between 4 different bbq sauces..sweet, smokey, hot etc. I did the coleslaw and mac n cheese!! So much food!! We then waddled over to the mining area. We were given a prefilled bucket of muddy sand and a small shovel. Also a gemstone card for reference. We had such a fun and memorable day here.

This excursion gets an A+!! All of the staff do everything in their power to be gracious, they are passionate about the manatees and the environment, and make sure every person in our 12 person party had a chance to see manatee. Even our smaller kids who were afraid!! The fan boat ride was also excellent!!! We will never forget this experience!

I recommend this tour to anyone traveling to the Orlando area!! It was such a great experience for me and my family! Our guide was very good and told everyone a lot of details about the things we saw! We will definitely be going back the next time we come to Orlando!

Everyone was very nice. The driver and your guide ensured nobody was left behind, they patiently waited for those who were tutelage. Lots of fun activities for the kids on the pirate cruise and nice crew staff.

30 mins was fine with small kids but older ones could easily handle longer. Lots to see and do at the site as well. Well stocked shop on site.