If you want it to be a pleasant experience, your wife must be comfortable aboard. There's a big difference in cruising with the
Navy and cruising on your own. We owned a 37 ft sailboat for years and my wife always felt that she was living in a hole. The solution for us was a
trawler. Now she has most of the comforts of home. My wife is also knowledgeable enough to handle the
boat. It has to be a team effort to
work.
Not sure how this fits with your question about
Hampton Roads. I am from the area though.