There are a few 'waterway guides' that outline just what you are planning.
Skipper Bob's "Anchorages Along the ICW" Guide and Skipper Bob's "Marinas Along the Intracoastal Waterway (listing of prices, etc.) are probably the two most used guides for the ICW - but are 'text' reports of bridges, known shoaling, favorite places to anchor etc. mile by mile.
Doziers "Waterway Guide" is another valuable source for area descriptions and local highlights.
For the Chesapeake - Shellenbergers "Gunkholers Guide to the Chesapeake" and Chesapeake Bay Magazine's "Chesapeake Bay Guide"
The ICW (and the Chesapeake) is a great place for going into small towns and gaining the local flavor. MD, VA, NC, SC and GA, especially in the small town, you will find genuinely friendly people and plenty of places to anchor. The 'northern neck of VA', especially Deltaville VA, and then entire state of NC have to be the 'friendliest'. The 'wilderness' of the tidewater' & 'low country' is stunningly beautiful with lots of wildlife and quiet creeks, etc. either on or just off the ICW .... would take one many years to cover this area adequately by boat.
The tides (9+ft.) and currents in some place to 3+kts (and shallow spots) in SC and GA can be a problem ... if you are in a hurry and cant wait to 'ride the wave of the tide'.
Many 'first class' all weather inlets can be found if you want to 'go outside'; but, if this is your first trip on the ICW and enjoy nature and friendly people then you can always go outside in Florida (Fernandina) and come back in at the Hawk Channel and continue down to the keys (missing all the 'ugliness' and pretension). Ocean Inlets can be dangerous in the 'wrong' weather .... recommend "Inlet Guide - Southeastern US", Jeff Dodge, White Sound Press as most 'gummint' charts exclude details of almost all inlets.
Florida will have little anchorages, and is mostly 'urban' from Vero Beach (great place for boaters) down to below Miami ... the ICW there just a concrete lined box with wall to wall houses with few places that permit anchoring due to the 'bulkheaded' ICW in an 'over-developed' area. That area of the ICW, especially on weekends, is simply over-crowded with many rude and discourteous boaters - Viva Yo !!!! Outside of Florida boats will slow down when passing out of good manners and courtesy, in Florida they use slow boats as slalom poles.
Between Palm Beach and Ft. Lahdeedahderdale there are over twenty bascule bridges and if you cant keep your speed up to 7 to 7.5 knots, you will simply not be able to pass on their strictly scheduled openings (you need a guide to find exactly when these bridges open).
Volusia County FL, seems to use out of state boaters passing on the ICW as a prime target prey species for revenue income .... be sure your overboard sanitary thruhulls are 'wired shut' and expect their excuse for a Buford T. Justice, Deputy Sheriff, to come along-side at any time for a boarding/inspection and general wholesale intimidation by a genuine legal thug.
A chartplotter with the LATEST charting is almost a necessity on the ICW but will only be reliable 98% of the time .... then you have to 'believe those temporary marks'.