The AAA for cruisers is really forum sites like this and others dedicated to cruisers like SSCA.org Otherwise download the NOAA Pilot Charts for the Atlantic (which includes the Caribbean) for long range planning. There are numerous "planning/routing" software
programs but they are really not any more useful than a paper chart and a set of dividers.
- - Specific waypoints and routes are dependent upon you boat
speed, and other factors that determine you average daily mileage made good and how often you need to get to port to replenish supplies and fuel
- - Posting
a desire for information on say Charleston to Miami
on cruising websites will get you plenty of suggestions and places to visit/stop and "local knowledge" about obvious hazards and unpublished tricks of the trades. You then combine these into your chart work
to see how you can optimize what you want to do.