Try begin staging plans from here
http://www.sanibelisland.com/Check with Nana Bosma or someone at Sarasota Sailing Squadron.
Hook up with a local dealer and sailors for selecting the date and begin filling the basket with sponsorship eggs.
Then ask yourself, "What is the best time of year to sail in the waters?"
Nana once told me that planing an event is like a pregnancy and must be tended to at least nine months out for lasting success. Her legacy lies in the growth of the Buzzelli Memorial Regatta.
Establishing a new event of magnitude these days requires gentle needlworking with local sailors, authorities, patience, and dedicated supporters (the more sailors - the better). Pick a team that will dedicate themselves to a two - three year campaign. Find a host club or public facility to host the festival. and so on...
Other events in the FL Panhandle such as the Juana Good Time Regatta and the Spring Fever Regatta at Nigel's, in GA, have prospered because they were established on a "sailors' fun comes first" philosophy. There might be an international US Sailing race officer running the event, but the "rules or loose" float plan is locked in the closet. A happy fleet is a returning fleet.