Queens landing is a great place to launch. Deep water. Alot of people anchor out and sleep, or pass out at the bars dock.
Vinnies is a little tough. There arent any public docks there. There is a little beach. Some people beach it, I think that is absolutely crazy.
Your best bet for bars are going to be Rusty Rudder, and Midtown Sundries. For a nice dinner with the lady I would consider North Harbor Club.
Most places wont let you take your dog up on the deck. Health code issue.
Youll have a great time. Im sure that it will be crowded on the water.