We've just got back from a fantastic 4 hour sailing trip with Captain Octavio with our two children (5 & 8). It was a perfectly relaxing way to spend a beautiful sunny morning in the warm waters around Anna Maria Island. Octavia was a chilled out captain who let everyone, including the kids, steer the boat. The kids loved him... More

We had a lot of fun with Captian Octavio. He was laid back from the beginning, has a great sense of humor and a story for every question. He let us each take a turn at the helm and he even took pictures of us. He made the few hours memorable and we all point to our time with him... More

We visited Anna Maria Island for this first time in April with our teenage daughter and her friend. We were looking for some activities and found Anna Maria Sailing Adventures on Trip Advisor. Based on the excellent reviews we booked a sunset trip and were not disappointed. Captain Octavio is very friendly and knowledgable about the local area. We had... More

We are a family of 6 including grandparents and had a fabulous experience! We saw dolphins our kids jumped off the boat and my daughter got to drive! And we all got to chill out on the boat! A must do! And i honestly thought i had mis heard the price!! Definately worth doing!! Loved every minute! If it was... More

Captain Octavio provides a fun, relaxed sail and has a great sense of humor! The sail was worth every penny and the sunset was the icing on the cake. I would highly recommend sailing with Octavio while in Anna Maria!

Sailing with Captain Octavio for sunset was a blast! He was fun and made sure we all had a good time. I HIGHLY recommend this while in Anna Maria!

Captain Octavio was charming, hospitable and a wonderful sailor. And he is very funny. He made sure we were comfortable, had something to drink, and were enjoying ourselves. One person in our party wanted to learn sailing and take a shot at steering the boat. Octavio accomodated him, with charm. He also made sure we got full vaue for our... More

Most unforgettable vacation experience you will have. Captain Octavio is 100% trustworthy. 3 hour sailing adventure rates are way to cheap for the experience of a lifetime. Captain is very hospitable and generous.

I planned a surprise sunset sail for my girlfriend on New Years Eve and we had a great time. OJ was a great host with an awesome amount of hospitality! He made us feel at home on the sailboat giving us full rain. Being New Years Eve.. he even invited us to his home following the sail to bring in... More