I'm on this trip as well and can answer some of these:

- 14-22; sleep aboard the night of the 14th
- figured we would overnight somewhere close on the 21st so people can get to their late afternoon flights on the 22nd
- yes, hiring a skipper for both boats
- skip is supposed to be sleeping in one of the V-berths

thanks to all of you for making this site so informative. it has been a huge help in planning for this trip.