My second post here. Great forum y'all have. First some background - I'm 32, been sailing literally all my life (Born in Jan, parent's had me out that summer

) everything from dinghy's to currently a Freedom 38. My wife sailed sporatically as a kid - her family would ocassionally charter & she attended sailing camp once or twice. After college she put some time in at Community Boating in Boston on the mercs. We have a 2 year old daughter who loves sailing (and cruising) on the grandparent's boat in Buzzard's bay & surrounding areas.
I've got the itch to get our own boat as we live 100 miles away from Padanaram, where my parent's keep thier boat. I would really like to be able to go for a sail after work or just out for a daysail on the weekend w/o the drive. I guess at 32, mooching off the parent's is getting a little old.

The closest harbor is Newburyport, MA (15 minutes) at the mouth of the Merrimack River.
My wife is generally more cautious than I, and does not seem to share my enthusiasum for becomming a boat owner. I've considered shopping on the sly & surprising her, but I think she would resent that & it would be "his" boat, not "our" boat. Attempts at getting her interested in the process have failed so far. My 2 year old daughter lasted longer at the Newport boat show than my wife did.

.
We've talked about getting a boat, but it was always "someday". I figure, better to get one now, before children are involved in sports/afterschool activites etc which will put additional squeeze on time.
I'm interested in a 30-35 footer that we can coastal cruise on. My wife has expressed interest in a "daysailor" that she & my daughter can take out on thier own. Newburyport isn't that friendly a harbor for a daysailor - 2 knot current + kind of "open" (rougher) water once you get out of the river. I now realize how spoiled I was growing up on Buzzard's bay.
I think her biggest hesitation to the larger boat is that she isn't confident in handling it. She is a competent small boat sailor, but can't seem to make the jump to running the bigger boat. I've tried to get her to do more while on my parent's boat, but I think the audience of experienced sailors intimidates her. I'll admit, I'm not the most patient instructor

nor is my mother (ahh the dreading Mother in Law

). It is very frustrating when I know, she knows what to do, but she doesn't trust her self to do the right thing.
I looked into a women only sailing lessons (womanship) she was somewhat interested, but didn't make time this summer to take a class (in fairness, not much available in New England).
So I'm looking for creative ways to get her more interested.
Surprise her with a vacation including women only sailing instruction someplace warm this winter?
Frostbite series? (kinda kidding, but hey if you can sail a small boat in the winter, then a big boat in the summer shouldn't be so intimidating).
Watch junior while she crews on a weeknight race series?
Daysailor in different harbor (Marblehead?) I've always admired the Herreshoff 12 1/2s.
Keelboat daysailor w/ outboard - J/24 or similar?
Pocket cruiser Catalina 250 or similar?
30 footer with a sailing dinghy? (still worried that she'll be great on the dinghy, but not the larger boat)
Sorry for the long post, looking forward to the replies.