You might state, what things you are interested in doing. Some people just want to tie up at a marina and eat out. Others are looking for an anchorage with no other people.
I live near Venice, and have sailed up and down to the keys 8 times or so.
Personally, if there were places on land I wanted to explore, I would drive.
For sailing, I would sail direct to Marathon, and explore the keys from there.
Actually, just until the wind
was right to cross the Stream and sail the Bahamas
. Cooler than FL in the Summer, and warmer than FL in the Winter!
Great sailing, only 58 miles or so from FL.
Need a licensed Capt. to bring the boat
back to FL, from the Bahamas
? Hint hint!!
Just inside, south of Boca Grande inlet on the west side of Useppa Island.
Just inside Boca Grand, north of the inlet.
between Boca and Ft. Meyers
Inside Gordens Pass
By mouth of Little Shark River (Bad mosquitos when sun goes down. Bad)
And by Thousand Islands.
Look at the charts
and make a plan, then ask about the inlets you want to go in, and try to get local knowledge. This last year, storms have changed some channels.
Hope this helps.