I have driven from Phila to both Annapolis and Rock Hall. The ride to Rock Hall is far less congested and urban - to get to Annapolis you either have to go around Baltimore or down the east side of the Bay and cross over.
I also took ASA 101 103 and 104 at various different sailing school (because of scheduling) and they are NOT all the same. Sure, the ASA standards are the same but there is a huge difference between a four day course and a two day course because sailing is a learning-by-doing kind of thing and the more you do it the more comfortable you will be.
Also, whoever said to do the coastal navigation (105) was right - It has no prerequisites but being able to read a chart and to figure out tides and currents from the published tables is a very good thing. Especially because when you first start out sailing ALL of the places you go are unfamiliar and being able to read the charts to know where you want to go is very good for your ability to relax and have a good time. You can do 105 online now - I did it with the Maryland School of Sailing and they sent a DVD and workbooks and I only had to go down there for the exam - Very much worth it and not very time consuming since they will give you the exam whenever you want.