Most everyone uses Skipper Bob's guides. There is one for anchorages and one for marinas. They also do updates online.
Aside from those I have two pubs onboard (we are talking ICW here going off shore is in some ways simpler). The Intracoastal Waterway Chartbook Norfolk, Virginia to Miami, Florida is a flip chart book with margin notes. I highly recommend this book although it is $70 it is worth it. The second is the Waterway Guide. Depending on where you start you may need the Chesapeake Bay Edition, the Atlantic ICW Edition and the Southern Edition. These are very good for seeing what there is to do ashore and marina information.
If you are not retiring immediately start by taking some classes (USCG, USPS, US Sailing, ASA) and see what you like. Charters are a way to try with out buying. Volunteering to crew with some of your local racers is one way to get free sailing experience. Once you have some sea miles under your belt, start with someghing smaller like a Catalina 22 (sail) or some smaller power boat (not a power boater so can't help here).
If you want more info, IM me and I'll hook you up with some good boating resources. I started in Haver de Grace, Maryland (northern most end of the Chesapeake Bay) and have made it to Saint Auguatine so far. I'm just heading south, but there are the snowbirds who run south in the winter and head back north in the summer. Then, of course, there's the Caribbean mate. Arrrr!!!
And since you are on this board, there are a number of interesting historical opportunites along the ICW like the Great Dismal Swamp Canal (surveyed by George Washington), Charleston (got adicted to cannons there), and Saint Augustine (more Cannons) just to mention a few.