Join Date: Feb 2010
Location: Narragansett Bay
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If you must have a mooring, the earlier you arrive the better. 2pm is our deadline, which also works in most places in New England too, btw. In the BVI, you shoudn't be more than a few hours from your next stop, it would be silly to travel the length of the channel in one day, although, I admit to having done it. Sail in the morning and plan to spend the afternoon relaxing at your destination.
It might depend on whether any are late sleepers. A 40 ft boat should be adequate for 6, as long as they are all tolerant of differences. Sleeping schedules and preferences for how tidy they are (especially on vacation) can cause stress. Too often, someone feels like they are pulling more weight because they get up earlier to get the boat ready, they are doing all the cooking and cleaning, etc.
We traveled with a schedule one year. Everyone had a different job each day. One was yours to clean below, another to clean the cockpit, cook, etc. It worked okay, however, not everyone can cook. However you decide it should work, I suggest all have an understanding before you leave.
As far as anchorages, I wouldn't be concerned about dropping the hook at all, particularly in <20kt winds that should remain directionally steady, unless there is a storm. Just be sure you have enough rode for the depth. The water is so warm and clear that it is very easy (and advisable) to snorkel down to the anchor to be sure it is set well. I've known some that have set the tip with their hands and reboarded to back down on it again. Then relax.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.