I suggest that you and your wife take some weekend trips and take some learn to sail courses. To give you a frame work for what u will see at the boats how you need some on the water
experience. Lots of seaside towns like boston, annapolis newport Miami
or even cities on fresh water
... Cleveland, Chicago, Pittsburgh have sailing schools.
Start training on a 20-24 ft sailboat, move up to a weekend live aboard course maybe on a 38 ft boat with an instructor and another couple. Get a sense of how much boat you want. When you think you are ready, charter
a boat- with or without a captain
- and spend a week sailing , sleeping, cooking
, man over board drills etc. it is great that you and your wife are both interested and positive. You may also find your kids
are going to want to sail with you so plan for space for them !