Tangerine, good to see you’re on a 5-day only! I’m doing a similar trip in June, but I’ll do 2- 5day laps with different crew, returning to Road Town in the middle to switch (my wife and are are taking 10 days with LOTS of friends and family)
It’s an ambitious itinerary, but if you get going early, I doubt it’ll end up a death march. I’ve done that same day starting from Cooper, or Norman, which isn’t THAT different really than going from Tortola…and The fact that you’ll have a capt on board probably allows slightly longer sails -since everyone will be enjoying the sail rather than trying to relax WHILE keeping tabs on the boat.
In almost every case though, try not to cram too much in, or at least be willing to skip something or shorten the sailing day…
I’ve come to the conclusion that when you get away from the traditional 7 or more day itineraries, you’re more likely to have to let some things go in the interest of comfort, and crew sanity.