So we're going to delay leaving Naples until Saturday. We'll head south to Little Shark River and anchor at the first turn. (Google Map). It's a known and recommended anchorage. If the weather holds, we'll stay there two nights and explore the Everglades using the tender. Watch out for crocs! Crikey! Hopefully the anchorage will not be too busy even though it's a weekend.
If the front is slower moving than forecast, we'll leave Sunday and only anchor one night or we'll leave Monday and head directly to Key West.
Distances are well within our capabilities:
Naples --> Little Shark River : 70 miles
Little Shark River --> Key West : 68 miles
Naples --> Key West : 110 miles