Anguilla is nice. But it is mostly about hanging out on quiet beaches and burgers and beers in beach bars.
Depending on what you are looking for, you may be disappointed with anguilla. When I was there, I had just finished bashing overnight upwind from the VIs, so a quiet spot was just what I wanted for a day or two. But if you're looking for a whirlwind leewards tour, I would suggest you skip it.
Also, some of those stretches might be too much. Unless your
charter allows night sailing, it seems unlikely you'll make some of those passages in daylight only, unless you have perfect winds.
For example, Gustavia to Charleston is 55nm straight line, you'll end up with 70nm likely in actual distance. Depending on the
boat,
wind, and seas, you may or may not make that during daylight.
I stopped at
St kitts when I did that last month. My philosophy is I would rather island hop than sail overnight if possible. As a full time cruisers I have the luxury of time though.
If you do make long stretches like that, I suggest leaving in the dark, to avoid arriving in the dark. It is always better to leave a harbour in the dark, since you have already seen it in the light than to enter a new harbour in the dark.
Enjoy your charter! And please be smart in your
anchoring. Maybe you already know all this, but from the number of charters I see here who can't anchor, it bears repeating: minimum 5:1
scope (more if possible), back down at 2000+ rpms, snorkel over it to make sure it isn't just caught on a rock or
coral, and be sure you aren't on top of another boat.