Weather-permitting, you have a pretty good plan. Lots of beautiful cruising grounds, protected anchorages
, gorgeous beaches, resort-style marinas, and options to duck inside if the weather
acts up when you are outside.
The Resort at Longboat Key Club is beautiful with great amenities.
Crow's Nest Restaurant at Venice has great food
Burnt Store Marina and Resort is very nice when you come in through Boca Grand Pass.
Cayo Costa State Park is lovely, with almost-deserted white sand beaches.
Cabbage Key just north of Sanibel is a fun place to visit with some really cool history
Naples, about 1/2 way between Sanibel and Marco Island is very nice as well.
You have chosen some great cruising grounds. Of course, your itinerary will be entirely dictated by the weather
. Don't even think about keeping to a strict schedule.
If it were me (just my personal cruising preference) I would relax and stay longer at places that I find enjoyable, rather than rushing just to be able to say I saw "x" number of destinations. The whole "8-ports-in-7-days" travel mentality doesn't appeal to me.