Where to Winter
Nobody else has mentioned it so I will.
My 2 cents worth? Key West. Continental U.S., yet perched at the top of the Caribbean. Way more tropical than the rest of Fla., medical, shopping, food isn't ridiculously priced (a great fish sandwich at B&O's or a pulled-pork at Sloppy's comes to mind), beer is cheap, boat parts and service readily available and about the only thing I found expensive was a gallon of gas and parking sucks.
But in my mind it's more fun than a hanging in the public square. Drop the hook in economy bay, the free anchorage between Wisteria Island (aka Christmas Island) and Fleming Key, where people on a budget or the homeless living free and easy on anything that floats hang out. A fee is charged to pumpout, land your dinghy or use the showers, but it's all available. Just be aware the anchorage is open to the NW so things coming that way in the winter months will rock your world...
Or my fav, hang on a mooring at Garrison Bight, where I had the great pleasure of boat sitting a buddy's 42' Endeavour, who paid less than $300. per month last winter, which included weekly pumpouts and parking a car. Dinghy to shore (free), jump on a bicycle or walk and you're at the nearby shopping/grocery stores. Home Depot too.
Or, my favourite place on earth, Old Town and Duval St. The best bar entertainment you can get. Schooners Wharf, Captain Tony's, Sloppy Joe's, a new one The Smokin' Tuna, Margaritaville (yes I am a pirate...J. Buffett), too many to list here. Go a little further to the Green Parrot, where the locals gather and shun the tourists- (their motto? 'No Snivilling') for some of the best live entertainment you can imagine. And cheap beer.
I have been going to KW for decades, but never longer than a week or two. Then I got to experience it for a winter season and I am hooked even more. Made some friends and played with some of the bands in the bars . Unfortunately my darling wife doesn't care for it for longer than a week at a time so it will never be home to me...much the sorrow. But I sure dig it when I can get back there.
Good luck.
Pirate Norm