I would agree with nolatom. You want a boat that is very affordable and that can get you out there and sail as much as possible.
In new England mooring
or slip space is going to be a big cost consideration. Close to home and the fees
associated with keeping a boat in New England
are not insignificant. A Cape Dory might just be it but others might also. That 27 to 30 ft range would seem most affordable and yet still provide a boat you can learn on and carry the family
in some comfort. You really want a boat that fits the budget
but works. You will change your whole opinion on what boats look good after sailing even a full season.
to sail is mostly about showing up. You take many day sails
and try various conditions to build experience and confidence. As you learn you establish better habits bit also start learning
what it takes for you and your crew to do the basics, get alonmg, and be happy. One person in a family
can not solo a boat over an extended period. You need them all doing something productive for yourself and for them. One unhappy crew member
and it wears on them all and on you. Not everyone learns or takes to thing at the same rate. In short doses it's not so hard to make them all have fun.
One thing my wife and I did when we started was to take classes
but eventually we took a week long live aboard class. We lived in San Diego
harbor for a week on a boat and each day the instructor came in the am and we went out sailing for most of the day. We had outr own boat for the week and personal instruction so it was a good valuable lesson as well as living on a boat for the first time.
I think formal instruction is a good thing when you add to it the daily practice of day sailing
. It's not easy getting the whole family all excited and able to sail and have them still like it. The short day sails
pay huge dividends. Find jobs for the whole crew and practice nautical skills in a fun way as much as you can even on shore.
One alternative you might investigate is any local "Sail Clubs". We joined a sail club the first year we learned. We paid a flat fee for one season and sailed all the club boats we wanted. At the time it seemed not cheap
but now that I own a boat it was a really cheap
story is my first sailing instructor was born in France
and her parents made her go sailing every weekend almost her whole childhood. She threw up on every trip for many years and hated it as a child. She teaches and races quite a bit today. She is a great sailor today.