I'm 66 and sail my H16 off the same Dunedin Causeway as you mentioned and feel comfortable sailing solo in the Gulf, but prefer a westerly on-shore breeze (just in case of a problem).
From Hurricane Pass you can easily sail south along Caladesi Island and Clearwater Beach and then back along the shoreline or then go through the Clearwater Pass and back up through the ICW. You can also sail north out of Hurricane Pass along Honeymoon Island, Three Rooker Island and Anclote Key.
Ideally, on-shore winds are safer and more fun since you can make fast beam reaches both ways and you can easily watch the scenery along the shoreline. If the wind is more from the east (on-shore), I prefer sailing in the ICW.
Besides the wind direction and speed, you may also want to take into account the tides since it can make it very interesting when you are sailing through one of the Passes while there is a strong tidal current. I use the following NOAA website's plots:https://tidesonline.nos.noaa.gov/plotcomp.shtml?station_info=8726724+Clearwater+Beach,,+FL+&flag=0