There are a bazillion boating/sailing options on Maui - the Scotch Mist is one of the very best, in my opinion.
The crew is small, very nice, and incredibly interesting...and the sailboat itself is a perfect size. If I remember correctly, their maximum passenger capacity is 16/17 people - and we've sailed at times with about 12 without feeling crowded. For their pricing, you get an incredible tour of the waters off Maui, as well as as much beer/wine/champagne as you can drink. Keep in mind that it's not the fanciest labels of beverages out there, but you're not paying any extra for it. One of the best values for your time/money. The crew takes good care of you as well.
My hubby was able to help raise the sail on a couple of our trips - always a cool memory, especially if sailing is new to you!!
Best time to sail with these guys? Whale season. November thru April there is NO better way to get up close and personal with the humpbacks. No engine noise - flying through the water - the humpbacks aren't as threatened by the sailboats compared to larger, noisy boats (and we've taken a few of those as well on different trips). Last year we were told to "hang on tight", as we had a competition pod of male humpbacks headed right for us. Incredible!!!
As far as family friendly goes - they do have seating in the back for younger kiddos. We have 3 kids, who on our last trip were 7, 5, and 3 - we haven't brought them on this sailboat yet because I think they'd freak out (and I love this sailboat so much I didn't want to ruin my enjoyment!). There are no true side walls on the front (just some roping and metal railings to hold) - and when you're truly sailing at times, you're tipped over to the side. When they're older (and not so scaredy-cat-ish), we'll definitely bring them out.
We, along with many family and friends, have now sailed with the Scotch Mist many times and it has become a 'Must-Do' when we're back on Maui.