Thanks all for the replies. I do like the sail from North Sound to Anegada a lot. I have also thought about the 3rd option of just cutting back to Cooper from JVD instead and heading to North Sound from there the next day.
The cut is redlined by most charter companies so I have always avoided it. I'm pretty sure the draft is 4.5 but maybe 5.5. We tend to make anywhere from 7-10 kts with this boat. It's not that big of a deal but it is irritating to watch other boats go through while you take the long way. lol
I also thought about heading across the North Side of Tortola and hitting Monkey Point and the Dogs to break it up and ending in North Sound before heading to Anegada but that sounds like a long day as well. May have to play it by ear depending on sea conditions that day.
I really don't want to spend two nights in Trellis but sounds like we would have to get up early to insure a mooring ball and that is probably not a definite. I believe there is a ferry from Marina Cay we could use as a back-up too but seems like it would be nice to have the boat in Trellis for the night.