I have done the Anegada Passage numerous times in that time frame [local school break], and had every kind of passage, short of a disaster, but I have always left from VG, either Round Rock or Pajaro Point, I favor the latter. The passage has been 16 -36 hours depending on the boat more than any other factor, bigger was better and motorsailing was sometimes needed for comfort or timing.
I am usually headed to St Barths but often stop in Simpson Bay SXM , an easy anchorage in the dark.
It is usually a beat to weather, but if you can wait for a better window it can be not bad. Big waves have been more of a problem for me. Easy to follow the overhead airplane lights heading into SXM all night too
Leaving from Anegada, avoiding the reef is a bit of a navigation event. And clearing out may be easier in VG.
Isles Les saintes is great as mentioned, Marie Galante is well worth a stop, St Barths, Nevis and Dominica are some of my favorite places to visit. Antigua as an ending will be fine.
You might consider treating an experienced friend along for the Passage and a few days in the Caribbean, it will be a relief for the Admiral for sure.
Have Fun!!