This is the 3d time I've tried to send this, but I'm new in the forum and don't know what I'm doing. The school I went to is below and I will gladly give you name/email of instructor if you want. Alan
http://www.flsailandcruiseschool.com/
I just checked Gangplank's website. Liveaboard rate quoted at $150 a month in 2011 (prices were couple of years old). Looked pretty good. I know that neighborhood is good. Wish I'd known about that when I was stationed at the Pentagon!
I was like you and was bashful about getting into a larger boat. I googled boating schools and found a 'school' in Fort Myers, Fla. So I spent a week on a 39' Mainsail and had a dedicated instructor who is a retired Navy Captain, Annapolis grad who teaches folks like me for coins and grins...