Suncoast Offshore: Grand Prix Festival
Personally, I really don't like this event, so for people like-minded to me, this is more of a warning than a tip. Every year, thousands of power boat profiteers and their fans come to Sarasota Bay for a combination golf tournament / boat race. The traffic in town becomes ultra-congested (which is terrible, because it's pretty bad normally), the stores are crowded, and the beach is always, always full - - bascially, there's no breathing room anywhere. Also, there's the noise. If you are on the keys you can here the roar of the engines from anywhere - including your $300 / night hotel room.
This event takes place the last week of June usually, so if no elbow room, noise, and a huge waste of fossil fuels is not your cup of tea, I'd avoid Sarasota all together then. However, if you have a desire to see shiny boats go really, really fast - charge on down!
Sarasota is an excellent place to go sailing. Besides having usually cooperative winds, Sarasota Bay is absolutely beautiful. Just don't drift off, or you just might find yourself waking up in Cuba.
Equipment: There are plenty of places to rent from, or you can check with New College of Florida to get in on one of their Saturday Sailing Clinics that are open to the public. Also, once a year, New College Sailing Club holds a cardboard regatta (boats made of cardboard with drunken students inside). It's a sight.