When running crewed charters I would never let guests setup an itinerary, I would plan stops according to what you liked, beaches, bars, diving etc. The reason is that it can set you up for disappointment if you don't go all the places you want to. I would have guests spend 45 minutes at Baths and be ready to move, others would spend 6 hours. So you have to have time flexibility.

I used to think I could sail you around BVI for 3 weeks and not repeat a day. Perhaps there are certain events you might want to hit, but realize things have to give before or after.

Other factors are out of your control, weather, cruiseship crowds, boat issues.

The only itinerary to do is plan your next trip.