Welcome to Flip Flops Sailing!
off season pricing use promo code: Offseason7
​At Flip Flops Sailing we provide captained private and public sailing excursions on a 30 foot catamaran named “Flip Flops”. A private sail means you get the entire boat for just you and your party and a public sail is open for others to join your party. We sail out of Holmes Beach on Anna Maria Island and out to the waters of the bay and, on certain sails, the gulf. We accommodate from two passengers up to a maximum of six passengers. Whereas a public sail on Flip Flops has a minimum of 2 and we will sail with just 2 passengers, a private sail on Flip Flops requires the purchase of 3 spots. We offer relaxing day sailing out on the bay ranging from 2 to 3 hours where you’ll have the opportunity to spot the local wildlife up close such as dolphins, manatees, or perhaps a sea turtle.  In the evenings you can book a sunset sail of 2 or 3 hours which is a beautiful time to go out for a sail.  Another option is to book one of the Flip Flops Sailing island excursions out to either Passage Key or Egmont Key at the mouth of the bay where you’ll have the opportunity to go for a swim, a snorkel, an island exploration, and a hunt for the perfect sea shell or sand dollar.  The island sails range from 4, 5, or 6 hours depending on which island you’d like to visit and how much time you’d like to spend at either of the islands.  To find descriptions of sails offered and the pricing of each sail you can visit that section in the menu options as well as a page with answers to frequently asked questions. For the menu options on a mobile device you can click on the 3 lines in the upper left corner of the page. Thank you for your interest in Flip Flops Sailing and hopefully we’ll get to take you out sailing with us.