|I have done this, about a year ago. You need to be real with expectations of all crew members. Everyone will be a crew member, sailing, mooring up, dishes, cooking, etc…. If everyone is the helpful non lazy type, shouldn’t be a problem. Then you have to determine who is responsible for the boat and signing the documents, and show that person some respect when you "use" the boat. Stocking the boat is important. There are no grocery stores in the middle of the sea. When in doubt, bring it along. Finally, what about emergency protocols? Everyone should be prepped in this, you never know who may get incapacitated. Do the folks you are going with keep their cool or do they go off the deep end when anything bad happens? Murphy’s law seems to find a way at times.
I say this because the one real experienced sailor on board is also the one who screamed bloody murder anytime anything happened. We were not going to die today (or anytime soon) yet, by his actions and voice, you’d think so. Really the only sour part of the entire great trip. Not so sure I’ll sail with him again….. Fortunately, we are still good friends.