Chris,
You don't say what your boating experience is, or how big the family is.
If you want to do day trips, and watch the weather as you start, the C Dory 22 is a great boat. But I would not set out non stop for Bar Harbor with 3 kids and a wife on a C D 22, with out some extensive experience.
I personally consider the CD 22 a 3 or perhaps 4 person boat (with modifications to the table and making and upper bunk). One has to realize that this type of hull form will pound in heavy chop and seas, and the boat has to go slowly in these conditions. There are deeper V's which have better handling characteristics offshore in rough weather--but they may not really be more "seaworthy".
Always look at the weather; not only where you start, but even more importantly at your destination and along the way. This coast can have fog, and heavy weather. You don't want your first experiences to be in these conditions. You may consider radar and you most likely will have a chart plotter as well as a dept sounder. AIS will become more comon on small boats and show where the larger commercial boats are in limited visability.
Be sure and take a sea trial--or get a C Dory owner near you to take you for a run. Be sure that you understand the boat. The 25 which I purchased had been abused by its first owner and I am sure that the owner frightened his wife, and that is the reason that he sold the boat. Take it easy, care for the boat, and it will take care of you!
