Not CIO, but while I think I can predict a few spots he'll suggest (sandwich place in Cape Coral, breakfast place in Ft. Myers Beach), I'll give you a few spots too. My sister (and one of my aunts too) lives in Sarasota and I used to live in Ft. Myers/Cape Coral, and one of my best friends from UM undergrad/UM law is still there.
Sarasota - get some pies from Yoder's. My sister and/or aunt usually brings a few up to Orlando.
Bonita - there's a very old, long-standing Mexican joint called Maria's out on Old 41 (not main US 41). Haven't been in about 10 years, so I'll let CIO tell you if it's still solid, but it's one of the places that's been there forever and was a favorite of the locals for a long time.
San Carlos Park - there's a great breakfast place called FK Your Diet on US 41, between San Carlos Boulevard and Estero Parkway. I'd be willing to bet you that CIO will tell us that he knows the owner...
Sanibel - there's a lot of great seafood restaurants out this way, but I always loved going to the original Cheeburger Cheeburger.
Captiva - I love Tween Waters and The Green Flash for ambience, and CIO will tell you about The Mucky Duck, but I liked going to the original Bubble Room, even if just for the desserts. Every year at "Taste of Fort Myers", the Bubble Room cakes were the first thing to sell out, both the Red Velvet and the Orange Crunch cakes.
CIO is the guy to talk to about seafood, I don't eat fish, so I trust him completely on that subject.