1) Hire a captain to assist and to lead/instruct; demonstrate only when necessary
2) Do some overnight trips to different locations
3) Research those locations including with Google Earth before you go
4) Make your chart your primary navigation source and use it and then refer to the chartplotter
5) Discuss what the plan is in detail before you leave the dock; after experience kicks in you will have your own self-contained discussion every time
6) If something makes you uncomfortable get a better understanding and realize if the angst is appropriate
7) Have fun
I was truck driver for over 20 years. If I had to drive a truck that I never drove before, I check first steering and brakes. Take her out and see how she respond to helm and how fast you can stop at different speed. I think that I am going to put a rear view mirrors on both side to help me with backing.