I have looked into some places and have found
some very nice places within walking distance
of the port to go out and enjoy our evening.
The El Convento Hotel is a 5-star Luxury hotel, within 5 minutes of the pier, and it looks like a decent area to me. I found a fine-dining restaurant in Old San Juan that serves tapas and has excellent jazz - called Carli Cafe Concierto - I'm really looking forward to checking this place out...it was recommended highly in the Frommer's travel guide.
I think it would be such a waste of time to stay on the boat! I want to enjoy the city - and I'm looking forward to it.