A couple of additional thoughts, from a lady who has done plenty of camping, trail riding, backpacking and
boating.
This sounds like a
family vacation more than a couples
vacation.
Do your
kids to like sailing? Have they been on the type of sailboat you are considering chartering? Have you? Knowing that before a week long crewed or
bareboat charter would be high on my priority list, personally. (I remember being the whiney, seasick 8 year old that really *didn't* want to get be cold and wet on a
boat all day or all weekend). Maybe a half day or full day crewed
charter closer to home would be a very wise investment. There are plenty of good sailing destinations in the Midwest - Northern Lake Michigan and The Apostle Islands in
Lake Superior come to mind. And you can easily sail for a day and include a lot of land based activities in a vacation in either location.
Also, you mention your sailing experience, but not your general
boating experience. If you already have solid general
power boating knowledge (navigation,
docking, knots,
radio usage, using preferred gadgets for example), I would expect that
learning to sail will be more of an expanion of an existing skill set, and you would likely be ready to go out solo more quickly than if you are brand new to boating. It's all a lifelong
learning process of course.
If your wife and
kids enjoy roughing it backpacking in the backcountry, even a simple sailboat will likely be luxurious. Enjoy your sailing adventures!