Regarding your thoughts...
1) What is the most beautiful place in the winter ?
There's lots of great places to go sailing in the winter...however, my vote goes to the Bahamas
, as they're still close enough to get back home from before cane season threatens to turn them into one of the worst places you can be in the summer !!
Of course, if you can afford this Dockwise Yacht Transport
then you can thumb your nose at mother nature & go to "where it's great"...at it's greatest.
2) What is the most beautiful place in the summer ?
That's a much easier question to answer, as the last place you want to be is on a boat anywhere near threatening weather
...so (on the east coast) that means heading up to the Chessapeake or other points North.
One possability that many folks overlook is to head
into the Great Lakes
& up to the North Channel North Channel and Manitoulin Island
However, since this thread is all about "Boating & RV'ing" I'll suggest that bringing the boat up to the Chez & then hitching up the trailer to go land cruising would be one way to handle it.
Although doing that would mean you'd miss the whole summer sailing season....& so it goes...
In our case, the right answer is to do "one at a time" as we intend to go cruising (with the boat) along the east coast
, the Keys & the Bahamas
(South & then North again) until we're too old (or tired of boating) & then we'll be land cruising with our Airstream trailer from there.
It may not be everyone's answer to the "summer/winter...north/south shuffle" but (for the Admiral & I)...it will allow us to avoid the cold of the north & the storms of the south, while we have a fair bit of fun in the process.
I'm looking very forward to being a very happy retiree someday.
Film at eleven.