I drove to Northern Florida once. It's easily 15-16 hours of driving. Southern Florida... oof! Not my idea of vacation. (I mean, sure, if we had a huge excess of time and it wasn't costing me income - i.e. later in life - we could mosey on down at a leisurely place, stopping early and often.)
I think the Seahorse Cottages look cute - I'm not sure I'd fly 1000 miles to stay there. But Sanibel has come up several times now, so we are considering the area! I actually really like the train idea; not sure if I could get my spouse on board. But time is precious - a day of travel costs me enough in lost income that I can probably do better on a flight.
I've never been beyond St. Augustine, so I know very little about Florida. I don't want to feel too much like a tourist, or like I'm surrounded by tourist. I know that's a tricky balance to find any time you travel, and especially if you want to feel a bit pampered.
Yes - we'll probably want to travel just before/after Thanksgiving, if it works with whatever affordable plan we come up with. I'll have to check out CheapCarribean as well. Thank you!