Donnie,
Welcome to Florida.
Consider cruising the West coast first. It’s less expensive, less pretensive, prettier, more laid back, nicer beaches that are more accessible, and a calmer Gulf. It’s all nice, but we think the West coast is nicer for a C-Dory with more ‘mom and pop’ marinas that welcome smaller yachts like yours.
You can face 30MPH winds while trailering in FL in Jan, so your dingy could see 100MPH winds @70MPH….and then a tractor-trailer passes you. I don’t think I’ve ever seen it being done and I wouldn’t want to. Having the option while boating will be nice.
We choose not to have a dingy due to the hassles of storage, inflation, deflation, motor storage and mounting, messing with another gas tank and filling it etc.
That doesn’t mean we don’t anchor out...all we need is a 2-burner Coleman propane stove ($20), a SS percolator coffee pot, a Lil’ Buddy propane heater for cockpit use and we can cook, heat water to clean up and bathe basin-bath syle with cheap 1lb propane bottles (properly stored overboard). Big boats need a dingy for ‘provisioning’ but you won’t...just select a marina near the Publix.
We choose against the hassles of a dingy or a generator. Every Brat crew will make their own decisions based on their own desires and boating experiences. There is no right or wrong answers for most issues. (However, I contend that even trying to stow an inflated dingy rooftop at Interstate speeds is a bad idea, if not a wrong answer).
The big bend area has some scenic rivers that only a small boat can explore, but no beaches until Anclote Key. From there to Key West is a nice 30 day journey. If you enjoy 5-star marina resorts as much as we do, the Moorings at Longboat Key is worth a couple of days with on-call courtesy van service to St Armand key. And a Publix 2 blocks away. Again, consider a stop at Calusi Island Marina south of Marco Island. Remember the new boating ed course and certificate needed for the Everglades and get that done now…
https://www.nps.gov/ever/planyourvisit/ ... rogram.htm
We hope your careful planning leads to a wonderful cruise!
John