If you can wait until spring, why not take your own boat south? You are not too far from the western entrance to the NY canal system. It's a beautiful trip east to the Hudson and would be an excellent shakedown cruise. I did the Catskill, NY- Key Largo-Bahamas trip back in 1999 and I'd do it again in a heartbeat. This was our first real live aboard experience.
If you want to begin this fall, you can still utilize your own boat. However, you may need to have it transported to Chesapeake Bay, or points further south, if you want to stay ahead of the cold weather. The ICW is a leisurely and sheltered way to get to FL.
If you wish to charter and you don't want to go way down into the Caribbean, FL and the Bahamas are good cruising grounds to consider.
Personally, I'd love the northern Bahamas and have kept my boat in Abaco for the past 5 years. It is a wonderful, safe, and picturesque cruising area. It's especially affordable during the Fall/Winter months, as this is considered their off-season. The only drawback is that it can get a bit cool during the winter months, with temps about the same as central FL. There are several charter companies located in Marsh Harbour and many marinas on many cays to choose from.
Many cruisers head further south to the Exumas for the winter months. Although I haven't had an opportunity to cruise there, I've read that Georgetown is one of the most popular cruising destinations for U.S. and Canadian sailors. If you like lots of folks around you, this would be a great place for you to visit.
I am not sure if there are any chartering companies in the Exumas that will meet your needs, but I just noticed that there in now a chartering outfit operating out of Nassau. This would be a great central location to begin exploring the Bahamas from.
As far as FL goes, the Keys are my favorite. However, expect to pay premium prices for dockage as this is their busy season. Also, there are not a lot of good, sheltered anchorages in the Keys and those that are (Marathon & Key West) tend to fill up fast.
Although I love visiting the Ft. Myers-Naples area, it's not really considered a cruising destination. Expect to pay top dollar for marina space.
Anyway, I hope I have contributed something useful to your deliberations. Enjoy your retirement!