About us

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Captain Octavio

Born in the coastal province of Cienfuegos, Cuba, Captain Octavio has always had an affinity for the ocean. As a child, Octavio enjoyed exciting voyages on his grandfather's sailboat, where he became versed in the art of sailing. Captain Octavio's grandfather not only passed him down his deep appreciation for the sea, but he also taught him technical instruction. 

Captain Octavio is a certified dive master, having obtained his designations from the NAUI, CMAS and YMCA, as well as from USCG. 

We bring the Carribbean to Florida


Anna Maria Sailing aims to provide you with stellar service and an outstanding experience. Having said that, we also want to make sure you have fun and create memories that will last a lifetime! 

Our values

  • Show consideration and appreciation for nature and its creatures. 
  • Respect your fellow passengers. 
  • Fun and enjoyment!  

Get in touch!

(941) 580-1502


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The easy way to experience Anna Maria Island's riches



Anna Maria Sailing Cruises are exactly what you need to relax and take in the majestic beauty Florida has to offer. 




Anna Maria Sailing offers both daytime and sunset cruises to cater to your every need and desire. You can experience the thrill and fascination of a close encounter with our local fauna, including bottlenose dolphins, turtles, and manatees. Or, you can prefer the peace and quiet that our sunset tour offers, where you can sit back and enjoy the scenery. 

“Bucket list check off !!!”

Best time ever enjoyed by me and my husband and his 84 yr old mother who doesn’t like boats and water ! Octavio warmed up to her instantly and kept us laughing with his outlook on life and amazed us with his wisdom !! Great night wish it never ended! We now call him our friend!! Thanks!
— Dougsrus, Fowlerville, Michigan
“A Little Bit of Heaven”

Octavio was a wonderful host - we went out into the Gulf for a bit, then came back to the intercoastal for smoother waters. The perfect way to see another side to the island and Longboat Key. I can’t think of a better way to spend an afternoon! Thank you Octavio for a relaxing trip!
— AtlantaSisters2, Atlanta, Georgia
“Fun on the boat”

Had a fun time. Took our daughter and son in law out. The drinks were cold and the sun was warm. Not much wind but still lots of fun. Octavio made us feel very comfortable. We saw lots of dolphins swimming near the boat. Highly recommend.
— Steve E., Charlotte, North Carolina
We went out with Captain Octavio on this 34ft sailboat. We had a blast. He was very accomodating and his prices were amazing. Next time we are visiting this area we will go out on his Sunset Cruise.
— Ikka S. Jackson, Township, New Jersey

Join us now for warm weather and cold drinks!