The Not So Big Sailboat For Anna Maria

Anna Maria Island has the great advantage of sitting on Tampa Bay. This means it’s one of the very best spots on the Florida Gulf Coast for sailing big boats. But it’s amazing how few large boats are seen sailing in Tampa Bay. Why are there not frequent regattas? In most parts of Florida sailing means having to motor in channels for a long time to get to open, deep water. Anna Maria Island sailboat owners have it made. From the shelter of their canal homes or homes on Bimini Bay, it’s a very short trip distance into the Gulf. There are no draw bridges to wait for. Once the motor is turned off and the sails are raised that’s what sailing is all about.

sunfish sailboat

Just because it’s a great place for large boats, that doesn’t mean Anna Maria Island is not also a good place for small sailboats. In fact, the sheltered, shallow waters of Bimini Bay make this the perfect place for small shallow-draft boats such as Sunfish. Even then, it’s important to be ready to pull up the dagger board to avoid hitting the shallow bottom. In fact, it’s a good idea to pay attention to the 2’ tide, and for the sake of the fragile marine ecosystem, sail only when there is clearly enough depth to be sure the seagrass bottom won’t be scraped. Just outside Bimini Bay, the waters are often benign in Tampa Bay, and it’s fun to explore the coast of the island in a small boat.


I grew up pushing my Sunfish several blocks to a sandy beach and sailing it in a shallow bay. But Sunfish are also fun to sail in the Gulf. How easy it would be to push a Sunfish or other small boat on a trailer, then pull it across the sand to launch and sail beyond the small surf we usually have here.

Sailing a small boat is no less sailing than sailing a big one. In fact, I’ve always thought that the bigger the boat, the more you are occupied with mechanical things, and this removes you from the pure essence of the sailing experience. The more minimal the equipment, the more in touch you are with the waves and wind. Windsurfing is the ultimate in terms of having the feeling of being “one” with the wind. It’s corny, but true. The sailor’s body is part of the mechanism that makes the windsurfing vessel move forward, and that’s as integrated as one can get in terms of sailing on water.

Most of the time the wind is not strong enough for good windsurfing around Anna Maria Island, unless you use a large board and large sails. But even a large sailboard is a small sailing craft. It’s interesting that the very first national windsurfing champion (1972), Bruce Matlack, now lives on Anna Maria Island. He enjoys sailing off of Bean Point, which is not exactly beginner territory. There are strong currents and the good sailing is far off shore, so it’s not a place to go unless you know what you’re doing. Because he uses a long board, Bruce is happy with the conditions here.

Whether on a long board or a short boat, sailing small craft in and around this small island is just one more wonderful way to experience Anna Maria Island.

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