St. Pete is worth a look see
The municipal marina is right downtown St. Pete. Not a lot of night life, but some, and the Salvador Dali museum is worth the trip.The Regatta Point Marina in the Manatee River (Palmetto - just at the entrace to Tampa Bay) is a decent marina, if a bit pricy. But there are a couple of good anchorages nearby if you just want to visit. I am told by friends that Sarasota has a nice marina. I think it is too close to the airport, but I haven't been there. It is at least 2 bridges in and down the ICW.ICW is problematic on the west coast of Florida. From Clearwater to John's Pass, it isn't much more than a ditch. There are plenty of places to get into and out of it if you want to. I would stay out, for the most part.