Central Florida · SAILING
18 tours
Here are the 15 sailing trips worth an afternoon, each with its price, its run time and the one detail that decides it for most people. Number one earns the spot.
3-hour Clearwater Tampa Bay yacht cruise with live music and optional gourmet 3-course dinner on the StarLite Majesty.
“Our waitress was very friendly and kind. I enjoyed my cruise so much and so did my family. We were celebrating my mom’s 84th birthday and the DJ congratulated my mom…..the food was delicious.”
Schooner Clearwater sailing cruise from Clearwater Beach, with dolphin and manatee sightings and true sail power for about 2 hours.
“Had a great time really enjoyed the experience. The captain and first mate were very knowledgeable and courteous to all the passengers. I would highly recommend this to anyone.”
Sail the Halifax River on a small catamaran hunt for dolphins and manatees in Daytona. Intimate group, comfy ride, $64.
“We had such a wonderful experience on our boat ride along the Halifax River! The seats were very comfortable, and we loved that there were both shaded areas and spots to soak up the sun. The weather was absolutely beautiful, which made the cruise even better. The captains were friendly, welcoming, and made the whole trip feel safe and relaxing. It was the perfect way to kick off our day in Daytona — we stayed at Caribbean Jacks for a super tasty lunch and cocktails—highly recommend booking this boat!”
Watch dolphins and manatees on a small Cocoa Beach catamaran, then cruise into sunset colors over the Space Coast.
“I did the sunset cruise and it was beautiful. We saw some manatees, dolphins, turtles and lots of various birds. The captain, Don, was lovely and insightful, teaching us about our surroundings as we went. 10/10 would recommend.”
4-hour catamaran from St. Petersburg to Egmont Key with snorkeling, wildlife, and 2 hours ashore for lighthouse and Fort Dade ruins.
“Every thing was great! A perfect day. We seen the dolphins and turtles, plenty of birds. The boat staff was friendly and engaging. Wished for time on the island. We would definitely recommend the trip.”
Drive your own catamaran through Clermont lakes and cypress marshes. 2 hours of guided nature chat, radio comms, and easy training. $95
“It was the best time, we all had an Amazing time. Nate was excellent and super friendly along with his crew member. Would totally recommend this for everyone”
Clearwater’s StarLite Majesty yacht cruise with captain narration, dolphin chances, and optional lunch on calm Tampa Bay waters.
“We booked this cruise for our last day in Clearwater. We’re very much looking forward to it. Starlight cancelled, saying that not enough people signed up. This was not a condition told to us when we booked!!!! Extremely disappointed!”
Clearwater Bay yacht music cruise on StarLite Majesty with live songs and optional lunch, 2.5 hours. Drinks cost extra.
“The experience was awesome! Food was amazing, drinks were swift, and the scenery was spectacular. Only wish the cruise didn’t go through the same area as frequently as it did.”
Private 2-hour sail on Lake Fairview near Orlando for $89. Learn sailing basics with Captain Dan and relax on calm water.
“Very relaxing and calming. Dan Pollock was very experienced and knowledgeable. Dan was VERY FRIENDLY, and engaged with conversation. He recommended great eating places to go and sights to see!!! Consider him a NEW FRIEND!”
Private 2-hour sunset sail on Lake Fairview with a licensed captain. Bring snacks and drinks, enjoy stars, calm views.
“What a great time!! We left the dock a few minutes early and sailed the flake waiting for the sunset. Dan was kind and funny. He made sure we were in the perfect place to see the sunset and even pointed out the stars and planets as they became visible. It was a great experience!!”
Private 40-foot yacht charter in Miami Beach for up to 10, with A/C cabin, bathroom, Bluetooth music, and water toys for 4 hours.
“I’m leaving a review because planning a trip can be stressful but if you’re looking for a boat, you just found it. We had eight girls for a bachelorette party. We fit comfortably on top. Everyone had an awesome time. The staff from start to finish were accommodating and friRead more”
Enjoy a private 2-hour sunset sail on Lake Fairview in Orlando with Captain Dan, hands-on helm time, and a cozy 25-foot MacGregor.
“My husband and I had such a great time sailing with Dan. He taught us so much about sailing and we were able to enjoy a beautiful sunset and awesome full moon. A great experience!”
Sail a classic schooner from Treasure Island through Boca Ciega Bay and John’s Pass, then catch Gulf sunsets with BYOB.
“it was an excellent trip..the staff was great and good interaction.. would highly recommend..”
Private 65ft yacht in Miami for up to 13, with A/C, sunpads, paddle boards, and crew-ready birthday celebrations.
“Captain David and the 2 mates were AMAZING!! The owner Angela was sooooo sweet and answered EVERY question I had. She even gave me a champagne bottle for my birthday yacht party!! Def recommend if you want a great time with good service!!”
Cruise Miami Beach Bay by yacht, pass mansions, then anchor for shallow swimming and a high-chance dolphin sighting, in a small group.
“They did not offer what was advertised I am requesting a refund. No swimming, swim toys, they didn’t dock to allow us to swim, no introduction to the trip, did not really engage with my friends and tried to make it up by singing happy birthday to me at the end…”
