Here is a another fellow boater looking for local knowledge and suggestions. His journey will encompass navigating the waters of Southwestern Florida past Naples, then Marco Island, then past the Ten Thousand Island region, and finally past Cape Sable, eventually ending up in the Florida Keys. At this point, a northward turn via the FLK Inside Route, will take him to his goal on the Eastern Florida shoreline in Biscayne Bay.
As of 2/25/13, Captain Kris has received some excellent advice from Captains Donovan and Bell below

Hello,
I’m planning or rather need to go from Fort Myers to Black Point marina in Homestead [south of Miami on the mainland shores of Biscayne Bay – editor]. Was reading the postings and looking at the chart and have a few questions regarding the posts.
The comment `winter waves’ ‘“ should I expect high seas in February? I generally like deep water so was planning to stay somewhat deep but I saw some posts that said charts are wrong.
Cape Sable shoals ‘“ is this difficult to navigate?
Boat. 34ft sail, 4.0 draft, 52’8 must height. 27 horse diesel.
Experience moderate. Looks like I enter the channel just south of east cape. couple questions:
1. What stops do you recommend?
2. Does the inter-coastal run cleanly all the way up from the inside or do I need to go outside?
3. Heading towards Marathon looks interesting because the water is deeper.
I appreciate any advice.
Kris

You will need to go outside at least until Gordon Pass at Naples where you can anchor in Port Royal or go downtown for a mooring or dockage. From there, inside to Marco is doable with the right tide as is inside to coon Key, but it is tricky in spots, so outside is easier. You can anchor in Factory Bay or Smokehouse Bay or dock in Marco. Cape Sable Shoals are not to be taken lightly so, if you go outside, you need to go pretty far south before turning Eastward (you can `jump the light ‘˜). There are other anchorages before Little Shark, but I haven’t used them and they would depend on the strength and direction of the winds. Anything at or above 20 from any other direction than North will be uncomfortable and we get lots of fronts this time of year.. From Little Shark it’s a straight run down to Marathon. Of course, you could do an `allnighter’ directly from Ft. Myers.
Donovan

You can anchor a mile inside Gordens Pass, then at Factory Bay in Marco. You can safely cut cape Ramano at the lime stone channels and anchor in calm water up the left hand fork heading towards Everglades City then a easy run to Boot Key Harbor. Email me if you want route, anchorage way point and draft information. We have a five foot draft 41 Hunter that has been on this route at least eight times. Email info is patriotus@comcast.net for info from 41 Hunter.
Dave Bell