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Bradenton Beach, FL

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Anna Maria Sailing adventures

4.0 (20 reviews)
Open • 8:30 am - 10:00 pm

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Me hoisting the sail

Alex was awesome. He's laid back and is fun to sail with. We were invited to help as much, or as little, as we were comfortable with. We'll definitely be back.

Sailing with Captian Octavio
Rachel S.

Great guide, wonderful person to spend the afternoon with! Captain Octavio is fun, personable, and laid back! Loved the afternoon would highly recommend to anyone!

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9 years ago

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13 years ago

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8 years ago

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8 years ago

Captain Alex was so nice and funny! we had an awesome and relaxing time, 10/10 recommended!!!

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8 years ago

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10 years ago

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13 years ago

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Review Highlights - Anna Maria Sailing adventures

“Octavio humored us and took us on a trip of the Bay instead of the Gulf due to storms.”

Mentioned in 14 reviews

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Whisper Sailing - Sailing with Whisper Sailing.

Whisper Sailing

(6 reviews)

My wife lucked into discovering Whisper Sailing when she was planning a weekend trip for our family…read moreto Anna Maria Island. Our weekend started with a morning sail with Captain Geoff, owner of Whisper Sailing, and we had a blast. I've done enough boating to know plenty of crotchety captains that have trouble with landlubbers, and Captain Geoff was the complete opposite. He was very friendly, personable and a wonderful host for our trip. Captain Geoff already had the sails up and ready to go at the dock. He helped everyone on board, we slipped off our dock lines, motored for maybe 50' and then killed the outboard. Just seconds after leaving the dock we were under sail. I was impressed to learn Captain Geoff had built the beautiful wooden boat himself. He chose the design because it only draws 1' so he can sail closer to the islands than you'll ever get in anything except a kayak, which is perfect for his eco-tours. Many tour guides get into their set routine and don't like to deviate from it, but Captain Geoff seemed so flexible and willing to go wherever there was something interesting that day. Our girls were VERY excited at the prospect of seeing dolphins, so Captain Geoff sailed around in an area where he frequently sees dolphins and sure enough we spotted some popping up. The girls were absolutely delighted! We were hoping to see manatees as well, but that will have to wait until our next trip. After watching the dolphins we sailed right up to the island for an up-close inspection of the shore-side vegetation and birds. Geoff shared interesting tidbits about the history and ecology throughout the trip. We had a great time on our sail, and will definitely return. Thanks again Captain Geoff!

You cannot miss this! A true gem! Captain Geoff is amazing. My husband, two children (ages 11 & 8)…read moreand I really enjoyed this sail. It was beautifully guided by Captain Geoff who clearly loves what he does. My famiy & I found it an honor to be on his beautifully crafted sailboat. I can hardly wait to go back for another sail. Don't miss this one!!

Catherine's Florida Charters - Captain and First mate hard at work.

Catherine's Florida Charters

(3 reviews)

This was a long over due Valentines Gift…read more However, it was so worth the wait. We couldn't have asked for a better evening; the weather was beautiful, the company was great, and most importantly, the Captain and crew were absolutely wonderful. We boarded promptly at 5pm. After going over some of the basic safety procedures, we were under way for a relaxing sail into Sarasota Bay. The crew, which consisted of Catherine, was very knowledgeable about the area and the boat we were sailing. The Captain, Kurt, was extremely friendly all the while he was maintaining a safe operation. During our sail, we managed to spot a manatee, several dolphin, a sting ray, and numerous bird life in the bay. I have to say, this part of Florida is just filled with natural beauty between the wildlife and the habitat around it. Although we did not venture too far from the home port, none of us seemed to have a care in the world, and for three hours, any thoughts of the real world melted away. I would highly recommend this sailing charter to anyone looking to get away from the hustle and bustle. Actually, I recommend this charter to anyone and everyone. This is truly an experience to remember.

We booked a sunset cruise for March 18th. The weather didn't look good so we called and moved to…read more3/20. A beautiful 74 degree day with winds below 10 MPH. They called at 4:30 and cancelled the 5:30 charter due to rough seas. From the photos below you can tell the sea is "VERY ROUGH". Very disappointed! We feel they had some other problem and lied to us.

Sara-Bay Sailing Charter and School

Sara-Bay Sailing Charter and School

(13 reviews)

Just finished an ASA certified two-day sailing class with Captain Sara. I must say she's a wealth…read moreof knowledge. After a brief introduction inside the Air-Conditioned office, we walked to the dock where she explained the ropes... literally. We cast off the Catalina 22 sailboat and made our way to the open bay. She handed me the tiller almost immediately. Both days were filled with all the points from the course curriculum and we practiced everything. The facility (office building) was clean and convenient. Shaded parking. Walking distance to a general store that sold a variety of drinks and sandwiches that you can grab and bring back during the lunch-break. We ate at one of the two tables in the breezeway overlooking Sarasota Bay... what a view! I left at the end of both days throughly tired but with a satisfied feeling of having learned a new skill. I'll be back for follow-on classes. If you're down in the area for vacation, or a local, carve out two days and pick up a new skill!

My wife and I recently spent 4 days taking the ASA 101 and ASA 103 classes through Sara-bay Sailing…read moreon Longboat Key, FL. We heartily recommend Sara-bay, and it's instructor, Sara A. Sara was extremely professional, very experienced, and posseses a talent gor teaching to her audience - especially if one student already posseses more sailing knowledge than the other. She was cheerful, witty, understanding, and extremely effective in getting critical points across to her students with respect tutoring her students. Our sessions ran from 9-4 each day, with a break for lunch. Both of us felt well-drilled, and confident in our abilities after these 4 days. I unqualifiedly recommend Sara-Bay and Sara A!

Anna Maria Sailing adventures - boating - Updated October 2026

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