The largest sailing group I've ever organized was 4 people, it was our first charter. It was a disaster mostly because the guest couple thought they were going on a luxury cruiseliner. Since then, it's been just my wife and me and we have it mostly down to a science. Now my wife has told her nephew and niece if they both graduate we will take them sailing as our graduation gift. Simple enough, but you know it never is...

So the nephew is a US citizen but the niece is Greek. They attend college in England/Wales so will be coming from London. Oh, and now the nephew wants to bring his girlfriend - ok but we aren't paying for that plane ticket! At least the niece and nephew are certified to charter and she has raced small boats competitively since she was around 10.

So we'll be coordinating 5 people and dealing with transportation, provisioning, boat size and cruising ground restrictions due to visa requirements if we take the boat from the BVI to USVI.

So, for those of you who have been in the position of setting things up for a group how do you go about it? To start I'm thinking either a largish (50'+) mono with 4 cabins or a 40'+ cat just for space and privacy and storage space but our budget is not unlimited and I usually find discounted boats. We usually do almost all our provisioning the first day and except for a few things along the way we are fine for two (and we eat on the boat almost exclusively) but I don't think we'll get away with that with 5 of us.

How do you communicate between two parties? Is it helpful to have cell phones? Should we try to meet up in STT or just have everyone meet at the boat?

How do you do provisioning - account for different tastes and such. I think my wife has a good idea about the niece/nephew but we have no idea about the GF.

What about assigning chores and duties. Is it better to ask, take a vote or what? With just the two of us she picks up balls and works the anchor and cooks. I handle the boat and do dishes.

I think she has sort of promised that we will try to take them to Vieques in the SVI to see the bioluminescent bay, we've sailed there before. Would it make sense to just get one of the big monohulls from Island Yachts (the 485's have 3 cabins and we've chartered with them twice before) and skip any immigration issues and the ferry/taxi issues to the BVI's?

Oh, and we just returned from the BVI's on Dec 9 and three days later my sister-in-law and sister got together and decided they wanted to do a charter with us. So, after this one they seem to think I'll be coordinating three couples! I need help...