I assume I don't need to tell you that this late in the year you run a serious risk of catching a strong cold front that could make the trip rather unpleasant and possibly not safe. I just spoke to a friend in CT yesterday and temps have already hit below freezing and high winds offshore
To get to CT there are no routes or options. You go inside (ie the ICW) or outside (the ocean) or a combination of the two. Starting in S FL, if you don't have a cold front coming you will gain 1-2 kts from the Gulf Stream
going north outside. I would recommend going inside around Hatteras, shorter and safer this time of year. Once you get to Jersey you have to go outside until you reach NY harbor where you can go through the East River and up Long Island Sound
I would think carefully about trying to attempt this trip on a tight schedule this late in the year. The pressure of trying to meet your deadline could result in going in conditions that would put you at risk. You can do the trip safely this time of year but would be really difficult to do it on a tight schedule.
If you insist on going get a good guide. Skipper
Bobs are good for marinas
. I also used Dozier's Waterway Guide for navigation
and supplimental information.