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Anna Maria Sailing adventures

4.0 (20 reviews)
Closed 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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7 years ago

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

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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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Dream Lover Boat & Breakfast - The Dream Lover at it's mooring

Dream Lover Boat & Breakfast

(4 reviews)

I'm always looking for unique ways to celebrate my husband's birthday - whether it be a zip-lining…read moreadventure, an afternoon playing with tiger cubs or an all you can eat party in a chocolate store. This year I kept the streak alive with a charming overnight stay onboard the Dream Lover. Our hosts, Kay & Jonathan (yes, that's Captain Cook) and their dog Skipper welcomed us aboard like long lost family. We enjoyed a beautiful breezy afternoon chatting topside over a nice glass of wine and some snacks. Kay and Jonathan gave us lots of suggestions for places to dine and we spent the evening exploring the area. Later that night after dinner we lounged on deck - enjoying the night air. Our accommodations in the captains quarters gave us a first hand taste of what living on a boat is like from the gentle rocking and splashing sounds against the hull to the unusual blender-like action when you flushed the head (that's boating lingo for toilet to you land lubbers!) Just two blocks off the sand, we took a 3 mile walk on the beach the next morning and came back to a wonderful breakfast and generous amounts of coffee! Then Jonathan treated us to a little tour in and around the surrounding marinas on their dinghy Bad Dog. It was the perfect way to cap off the stay. If you are looking for a unique place, if the idea of life on a boat intrigues you, if you are willing to exchange the cookie cutter experience of a chain motel for a one of a kind, authentically nautical overnight experience (with all the quirks that entails) this is the place for you.

I cannot say enough good things about our weekend aboard the Dream Lover! Jonathan and Kay we're…read moredefinitely kindred spirits- so welcoming made us feel right at home. We enjoyed spending time with them and learning all about the boat- something we have never thought much about! Breakfast was to die for, and the wine a fantastic added bonus;-) I have never felt more at home while on vacation- and that is NOT an exaggeration! The boat is well kept, clean, and oh so comfortable. It was such a unique way to spend our anniversary- I cannot wait to bring our daughter back for a weekend adventure and would recommend a stay to anyone looking for something out of the ordinary.

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

Catherine's Florida Charters

(4 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.

Anna Maria Sailing adventures - boating - Updated May 2026

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