dsprague,good for you, sailing will get in your blood. My first boat a International 23 I went to the Bahamas in. Went from Jupiter inlet to West End. Took 9hours. About your question, I usually leave Tampa Bay then
anchor at Ringling Bride for a early startout to the gulf. Then I pullin at Venice inlet turn right and
anchor inbetween the green markers that are large balls behind the houses on the right. Then I stay at Charlotte Harbor. As you go south on the right after the first island you''ll see a bunch of stakes, one group looks as the remains to a stilt house the other a dock. Go between the ones on shore and the others about 100 feet off shore. Follow it around to the back. super anchorage.Then on to naples,I
anchor inside the first bend. Also nice. From here its either the Dry Tortugas or Marathon. Once your past 10,000 islands just follow the park markers keeping them on your port as you head south. I''ve made this trip many times and its always cool.Remember the only place to pull into in case of heavy weather is Little shark River between Marco Island and Marathon. good sailing .Don