Rob wrote:

Matt,

Get the boat. Make sure you have a reliable engine for it, read as
many sailing books/websites you can get your hands on and talk to as
many experienced sailors as you can find. I never met a sailor more
experienced than myself that was not willing to teach me a thing or 2.
I bet you can even get an experienced sailor to sail with you the
first few times you take it out. That size boat 28-30 ft. is not that
difficult- take it out on days with light winds to learn and use the
engine when you need it.

PS. Make it easy and comfortable for your wife and she will love it
too.

Good luck and feel free to email me with any questions.

Rob

Good advice.

Might I also suggest that the first few times you take her out you very
carefully and deliberately choose not only the best weather but the
nicest places. My wife (now of 26 years) still remembers the good times
of our bay-cruising days before we were married & kids &c and is now the
prime mover in our plans to retire into a large ketch somewhere in the
Pacific.

Worked for me.

Regards
John M.