My wife and I have done both family trips as well as trips with guests. Enjoy both of them. We find it a little bit challenging to find the right people to invite on our trips. I'm pretty easy going but at the same time I really want someone that (a) has somewhat close life style, (b) is easy going and definitely not annoying. We own the boat so for us it's not a cost consideration but if I was chartering I would think it a mistake to qualify someone to join based on their ability to pay their share vs. (a) and (b) above.

Space has never been a problem for us. Even when the boat was "full" we were out with family and/or friends we enjoyed. I told my wife the other day that I would sleep standing up in a closet if it meant going out on a sail trip.