There really isn't a good answer to your first question. A lot of it depends on the wind, and that can be quite variable. Also, the skill of the crew, and whether you'll be sailing at night, or stopping for the night each day, will have a major impact on how far you can travel each day.
Do you have an autopilot or windvane, or will you be steering manually the whole way? How big is your crew? How experienced is your crew? These are all things that will affect how long it takes to make the voyage.
The best program for the Mac is MacENC. It will allow you to use the ENC files that you can get for FREE from NOAA.