This is a "must do" if you are anywhere near Anna Maria Island. Captain Octavio is a natural charmer and obviously not only knows his way around a sailboat, but can tell a story. We sailed on Thursday evening of last week and saw a beautiful sunset. The trip out included spotting a large sea turtle and lots of information... More

This was our first trip to Anna Maria. My girlfriend and I decided to take the Sunset Sailing package. I couldn't be more happy with the decision. Octavio was amazingly friendly and funny. The drinks never stop, so I hope you like Rum n Coke! The whole experience lasted a bit more than 3 hours, but it was worth every... More

My wife and I have lived on Anna Maria Island for 13 years, but had never taken a sailing excursion. We had a friend visiting who insisted that we give "it a try" along with him. We are really happy we did!!! What a wonderful experience. Captain Octavio made the excursion fun, informative and personally rewarding. One could tell immediately... More

On our third trip in as many years to Anna Maria Island, we decided to take a three-hour sunset sail with Captain Octavio of Anna Maria Sailing Adventures. I only wish we'd met Captain Octavio on our first visit to the island. He was thoroughly entertaining and we enjoyed every minute. Our trip started across from Coquina Beach on the... More

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!