Florida to New Orleans

My boyfriend and I are planning on taking a trip to Florida to visit his grandmother, then driving to New Orleans in a rental car. We expect the entire trip will take about two weeks, with one of those weeks being on the road. Right now we are planning the trip for November 30 to December 15 and I have a rough schedule of what we are going to do, but I'd like some input before I start making reservations for things.

Here's our itinerary so far.

Day 1-3: Boca Raton, Florida (visiting his Grandmother)
Day 4: Drive to Miami and spend the evening there. It’s a short drive, but we want to hang out in Miami for awhile.
Day 5: Drive through the Everglades to some place on the Gulf Coast. My original idea was something near Tampa, but someone suggested Sarasota or Siesta Key.
Day 6: Drive to Crystal River. I love manatees and I heard this is a great spot to see them.
Day 7: Drive to something further up the Gulf Coast. Pensacola? Panama City? Apalachicola? Maybe even Biloxi or Gulf Port, Mississippi.
Day 8: We might add another stop here or we might just drive straight through to Baton Rouge. It'd be a lot of driving in one day from Pensacola, but not that bad from a place like Biloxi.
Day 9 (or 10): Drive along the Mississippi River to New Orleans. In other words, going the “long way”. I heard there are a lot of neat plantation houses along this road.
Day 10 (or 11): From here on out will be spent in New Orleans. I’m not sure how much time we should stay. It’ll be somewhere between 5-6 depending on what we do on Day 8.

So I'm open to suggestions. My boyfriend and I are pretty adventurous and don't mind going off the beaten path (keeping in mind we are in an economy rental car), but we certainly don't mind stopping in big cities either. We have a pretty wide range of interest so we'd consider pretty much any idea. Most of our road tripping experience is from the southwest region of the country. This is the first trip outside of that area.