Done that same trip a few times.
Get out to the Gulf by Pass A Grille channel. What we do is we'll leave on day one in the afternoon and get to Egmont Key by nightfall. We'll anchor out and have a nice dinner and get to bed early. On the 2nd day will leave Egmont through the South West Channel at sunup and sail to Venice, FL. We will head west for a while out to deeper water to avoid traffic and lobster pot fields. Venice inlet is easy to navigate at day or night, right at the entrance on the inside is the Crow's Nest Marina & Restaurant. Very nice friendly marina. If you go there check the tides against your intended departure time as there is quite a fluctuation and strong currents. If you leave Egmont around 7:30 AM you should be there by 5:30PM it is approx 52 NM.day three takes us from Venice to Naples, FL. You are looking at approximately 75NM or a 15 hour sail. So you may want to time your Venice departure to leave in the afternoon and sail overnight or leave at early light to get there in the evening. The pass into Naples (Gordon's pass)is easy to navigate at night the town is about 5 nm inland navigating through a snaking Gordon River. At night a torch light and an alert crew is a must to stay within the markers. The aid of a chart plotter will help you find the markers. The City Docks is an excellent place to tie up. Here we usually sleep late and stay the day in town. Day 5 (we spent day 4 in Naples) we head out and go Cape Sable where we'll anchor out at any cove near East Cape. We'll leave Naples around 4:00 AM and get to East Cape by 6:00 PM. It is about 70 NM. Day six, at this point you are about 110 NM from Miami and we do it straight through with an overnight crossing. We leave around 6:00 AM straight to the pass at the 7 mile bridge near Marathon Key and take the Hawcks channel all the way to Isla Morada where we will spend the night at a Marina in Florida Bay. Watch the tides for going in or getting back out. Here we have a choice of continuing through Florida Bay or going back out to Hawcks Channel. I guess it depends on the tide and whether you want to sail or motor. From Seaside you can enter Biscayne Bay through Angle Fish Creek or Cape Florida. It makes for a good daysail, leave early and youl be at Crandon by early afternoon. Now this is a leisure pace we have done the reverse route with adequate crew in three days. I like Biscayne upper Bay as is deeper than the lower. Day sails to No Name Harbor and Elliot Key or Boca Chita are very enjoyable. Get a a chart and a cruising guide as my distances may be a little off and the boat speed may be dependent on the wind which may throw the estimated times off. Good Luck