Welcome to Bimini Bay Sailing Lessons

Small Sailboat Sailing School

Bimini Bay is a beautiful, sheltered body of water nestled inside Anna Maria Island. It is the perfect, safe place to learn to sail -- and we often see dolphins! Bimini Bay Sailing is just minutes from Holmes Beach, Longboat Key, and Bradenton, snuggled between Tampa Bay and the Gulf of Mexico.

Take Sailing Lessons on our Sunfish Sailboats.
Or on a very stable WindRider 17 Trimaran, with a quiet electric motor for uncertain breezes.
Or on your own small sailboat. I also offer powerboat docking lessons on your own boat.

If you already know how to sail and you want to rent a sailboat, for your safety and pleasure, I will still do a skills and safety review. Then I'll go out with you as your coach/guide, on the same sailboat, on a separate Sunfish sailboat boat, or on a kayak. This is to make your experience as safe and pleasant as possible.

Captain Floyd Jay Winters, an instructor for Bimini Bay Sailing since 2012, has taken over the helm of the Anna Maria Island small sailing school. (He is fully vaccinated.) Jay will focus on giving lessons, either at Bimini Bay Sailing on a Sunfish or a WindRider 17 Trimaran or at your location on your own dinghy sailboat or keelboat. To schedule a sailing lesson, you can reach Coach Jay Winters at 941.730.2719 or click on the [Contact] link.

I encourage one or more follow up sessions to refine your skills and have to opportunity to get more sailing time on your own. Parents or spouses are welcome to watch the sailing class and take photos of their kids or spouse as they learn to sail. Click the [Lessons] link for more information on what is covered.

Click the [Photos] link to see beautiful photos of Sunfish at Bimini Bay Sailing School.

Have a new Keelboat or Powerboat? I also give small keelboat and small motorboat lessons on your boat, covering such topics as docking, backing up, pivot turns, and more as I share local knowledge of our waterways...

A Father and Son Tacking a Sunfish (29 seconds)

For the past 11 years, Bimini Bay Sailing has offered a sailing summer camp through the Anna Maria Island Community Center. And once again this past June 2022, fourteen young sailors had the opportunity to safely experience the excitement of their first exposure to sailing during our mini sailing camps at Bimini Bay.

Receive sailing lessons at our small sailing school or just refresh your sailing skills in beautiful Bimini Bay. The magical waters around Anna Maria Island are warm, clear, and uncrowded.


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Bimini Bay Sailing, Anna Maria Island, Florida