X2 what Blackbird says...
I will add 2 things..
1. Don't skimp on clearing Cape Romano as you depart Marco/Naples. I run offshore approx 10 miles to the Cape Romano Shoal Lite and then set a course for Daymark Green#13 off Vaca at Marathon. That distance is approx 80 Statute Miles. Blackbird is correct when he says it's unobstructed with mangrove islands & shallow water. Be aware that the tide roars thru Vaca Cut if you attempt to get your 360 under the fixed bridge. I would head on to 7 Mile Bridge and cut thru there; it's not that much further West.
I would also be wary of running autopilot thru Fla. Bay with the aforementioned lobster pots, especially during the winter months.
2.) The prevailing winds,(except for the localized afternoon seabreeze which usually ends South of Marco) are E/SE/NE. Your 360 can take a lot, but if it's too lumpy during your passage, you can cut back in towards shore South of Cape Romano and come out near Indian Key Channel to Everglades City. Parallel the uninhabited coast all the way to Fla. Bay, staying a mile or so offshore in approx 10 ft of water and you'll have a smooth ride. When you clear Cape Sable, you'll be out of the lee of the mainland and have to cross the last 25-30 miles in open water. When I run close in, I set a course from NW Cape lite (near Cape Sable) to Green #13 at Vaca.
Okay, 3 things...
3.) Make sure you have the fuel range to go from Marco to Vaca at Marathon. There are only alligators, snakes & sawgrass between the 2 destinations.
