My wife and I usually take at least six other people with us, relatives and/or friends. We've had as many as 10. Most of the people we take have been with us before, but they know that I am serious about safety and will refer them every time to safety tips I put together from comments made on this forum... https://docs.google.com/document/d/1AfTmhz9wGZyxGm98-FVAOYqVO7OZa-6HEAeFyjVo6vU/edit?usp=sharing

That kind of sets the tone for the voyage.

I ask everyone if there is anything they won't eat and what their beverages preferences are, then order provisions through Riteway... http://www.rtwbvi.com/ on Tortola and have everything delivered. Beverages are usually ordered from Tico... http://ticobvi.com/

An evening start helps deal with late arrivals and allows everyone to easily stow their stuff into their berth, get used to climbing around the boat.

The first meal together that night is at a restaurant, so we can relax, get to know each other and talk about what to expect.

After a boat briefing, I leave the dock with as few people as possible involved, especially newbies. I just tell them to relax and watch for the first day or so. After that, I will allow them to help sail if they are so inclined. I let everyone handle the helm while making sure they don't do something they shouldn't.

I always charter a 50' or larger monohull with a generator and A/C. Just makes things more pleasant for everyone.

Sometimes I have to deal with a recalcitrant crew member, so I just take them aside privately and help them understand that we are all on vacation and to wait until the trip is over to express any negative feelings about anyone or anything.

I have had kids as young as five-years-old and grandparents on the boat. I give everyone several options so they feel like they have some say about what to do (snorkeling, manning the helm, reading quietly, playing games, a ride to shore in the dinghy so they can go exploring, etc.)

I enjoy cooking, so I begin the trip by doing that myself and asking if someone can cuts some vegetables or whatever. If someone else wants to cook, I let them. I make sure everyone has a chance to do the dishes afterwards.

I usually wake up before the sun broaches the horizon, make some coffee, check the weather, and plan the day. Often, as soon as there is daylight, I will start the motor, cast off the mooring and head for a destination. Everyone on the boat usually knows I don't need assistance, that they can take their time getting out of bed, and that the boat will rock a little bit. (If there is much chop, I will ease off the throttle.)

Most of the crew usually feels like this is the best vacation they have ever taken, even though they were uncomfortable at times. For me, it is the only vacation I will ever take.