[mccary]

If you are seeking a place to start sailing that will be "easy" I might suggest The Chesapeake Bay, it is the largest estuary in the US and has over 4000 miles of shoreline for cruising. It sports 30+ rivers and countless creeks for anchorages. It has many nice family destinations. In the summer the temps can be a bit hot and late summer you will find more than enough jellyfish to discourage swimming.

As for a boat, that is a personal question. It will depend on how friendly your family is and the ages. On my first boat I did a 2 week cruise on a 22' boat (no standing headroom) with my wife and my young daughter and my in-laws! It was more than crowded and it it wasn't for the fact we didn't know how crowded we were we would have not enjoyed ourselves as much as we did. I now sail a 27' boat and subscribe to the theory: 6 for drinks, 4 for dinner and 2 for sailing is about right. Of course I have had 5 people out for an afternoon but that is different.