George...there are NUMEROUS threads here with info on the ICW and BAHAMAS crossing and MUCH more detail than any one post can cover. If you hit the advanced search function and type in ICW and my screen name and Bahamas and my screen name...you will likely find most of those threads. Lots of reading there for you.
Having said that...I would further suggest that you take BillyRuffins advice and work your way down through long island sound and the NYC/NJ coastline as you will be able to find put in spots and safe harbors for each night as you seem to wish. Then it will be up the Delaware and down the Chesapeake to the start of the ICW in Norfolk. This would be a good spot for your wife to join you as you can stick to the ICW from there. There are FEW day hops outside on the ICW...most require overnights to make any sense.
I note your attention to fuel and filters...also attend to engine spares, alternator belts, impellers etc. as this is essentially a motor vessel trip...doing 50-60 miles a day. But lots of fun the first time! Pick up a copy of skipper bob's guide to ICW anchorages...and make sure your anchor system is DAMN good...it is the most important piece of equipment for the trip! Radar is complete unnecessary on this trip once you clear New England.
I hope you are upgrading your battery and charging plans as well since once you start living on the hook and not moving every day...energy use/storage will become big issues for you.
The Bahamas is a very realistic and achievable goal for you. I am pretty confident you won't make it to Domenica in a C30...but you'll figure that out yourself along the way.
Anyway...read the suggested threads and come back with more specific questions IN THOSE THREADS so that the resource is available for all in one place.
No longer posting. Reach me by PM!