We just did the trip last april in our endeavour
43. From No Name harbor on Key Biscayne we took Hawk channel and motored to Marathon. That was day one. We anchored just to the west of Boot Key. It was a good anchorage. The next day we motored/sailed to Indian Key in the 10,000 islands. Again a good anchorage. So that's day two. Day three we sailed/motored to San Carlos
bay found a place to anchor
and spent the night. Day four we motored up the intercoastal to Sarasota
and anchored downtown. Day 5 we motored up the intercoastal till it comes out just west of the Skyway bridge, then we sailed to where we have a slip in St. Pete, the Harborage Marina. Since the boat was new to us we took our time and didn't push it.