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Anna Maria Sailing Adventures

Certificate of Excellence
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Address: Bridge Street, Bredenton Beach, Bradenton Beach, Anna Maria Island, FL 34217
Phone Number:
+1 941-580-1502

TripAdvisor Reviewer Highlights

Read all 184 reviews
Visitor rating
  • 164
  • 10
    Very good
  • 3
  • 1
  • 5
Captain Octavio is king of the sea

I went out on the water w/ Captain Octavio and 2 of my girlfriends. He was the coolest and nicest guy ever. We had so much fun. Lots of drinks and I got waaaay too much sun. It... read more

Reviewed 2 weeks ago
chicago, il

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184 Reviews from our TripAdvisor Community

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Showing 183: English reviews
chicago, il
Level Contributor
6 reviews
common_n_attraction_reviews_1bd8 5 helpful votes
Reviewed 2 weeks ago

I went out on the water w/ Captain Octavio and 2 of my girlfriends. He was the coolest and nicest guy ever. We had so much fun. Lots of drinks and I got waaaay too much sun. It was the best day w/ me and my friends. Thank you Captain! We will see you again!!!

Thank traciib76
Level Contributor
89 reviews
12 attraction reviews
common_n_attraction_reviews_1bd8 74 helpful votes
Reviewed 27 March 2017 via mobile

This was an experience! Octavio says he stole a gun boat from Cuba and steered it to America 20 years ago. He brought along his girlfriend, his girlfriend's friend, and an airplane pilot who ultimately ended up steering the boat most of the time and docking it. The girlfriends brought along piña colada's and margaritas that were fabulous. My wife... More 

Thank MJH161
Bridgewater, Massachusetts
Level Contributor
7 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 24 March 2017

Octavio is one of the easiest going captains one could possibly meet. The trip was more like traveling with friends than a paid charter. The trip was a no frills trip. and the sailboat wasn't spit and polish but the trip was very well priced, Soft drinks and cocktails were provided. I will be back as long as he'll let... More 

Thank 4000f00ter
Ponte Vedra Beach, Florida
1 review
Reviewed 16 March 2017

Brought our 3 "tweens" on cruise with Octavio- all 3 said it was the highlight of their trip! He is so laid back and had lots of great stories. Overall we highly recommend this activity!

Thank SlingToby
White Bear Lake, Minnesota
Level Contributor
44 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 56 helpful votes
Reviewed 12 March 2017

My husband and I have had some great sailing experiences (as passengers) in the Caribbean and Florida. While staying on Anna Maria, we booked a three-hour daytime sail with Captain Octavio, based on other TripAdvisor reviews. We were able to easily book online and looked forward to our 11 am outing; the day proved to be warm and moderately windy.... More 

Thank Katrina208
Port Washington, New York
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 6 March 2017 via mobile

Had a wonderful relaxing evening for the sunset cruise. Octavio is the best. Lots of lively conversation and great sailing.

Thank ArchDesign
Philadelphia, Pennsylvania
Level Contributor
106 reviews
10 attraction reviews
common_n_attraction_reviews_1bd8 43 helpful votes
Reviewed 22 February 2017

With another couple, experienced sailors, which we aren't, we booked a 3 hour trip into the gulf with Capt. Octavio. The combination of fair weather, light winds, generous refreshments and a story-telling commander made for a most enjoyable cruise. A most memorable trip we'll look forward to doing again.

1 review
Reviewed 21 February 2017 via mobile

My husband and I had a great afternoon with Captain Octavio! He clearly loves sailing and spending time with others. Great story teller and delightful host! The views and dolphin sightings made our trip complete.

Thank Mooski99
1 review
Reviewed 5 February 2017 via mobile

My husband and I went on a sunset sail with Captain Octavio and had the most delightful time!! Octavio was funny, informative and all around charming! Next time we are in the area, we will look him up to take another cruise!

Thank Laura G
Columbia, Maryland
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 5 February 2017

My husband, daughter and I had a fantastic time sailing with Octavio this afternoon. He was engaging, informed, always helpful and cheerful, and made sure that we had a positive experience, including ensuring that we saw the best views of the sunset. Fabulous time!!! We'll do it again! He also recommended a restaurant -- Blue Marlin -- to go to... More 

Thank murphmarsh

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Questions & Answers

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?