We'll be setting sail out of Sea Cow Bay on October 30th for 10 Days, returning on Saturday November 9th. Our plan is to stop at Norman the first night. From there I guess we can head either clockwise or counterclockwise, but we'd like to stay 2 nights in Great Harbor, 3 nights on Anegada and 2 nights at Levericks on VG. That leaves us with 2 nights open.

In looking at the Cruise Ship schedule I see they are in port on November 3-5 which suggests we stay away from VG and The Baths then? We plan on taking a day and renting a vehicle and driving the island and would like to avoid the crowds. We'd possibly like to be at Levericks on Friday November 1st for the BBQ and Moko Jumbies if they've started up by then for the season.

Any thoughts on scheduling/direction and where we might want to stay the extra 2 nights? As usual I'm overthinking the entire operation...

You might consider Cane Garden Bay, (I always pick up some rum there) and Cooper Bay if not busy yet.
BTY, Looks like we might meet up in Anegada. I believe you might be leaving Sea Cow Bay a few hours before we get there. We'll flying an O.S.U. flag. Hope to meet you. Naturally weather can change plans on a days notice.

Jag,
We’ll keep an eye out for you, we’re most likely headed to Norman and The Willy T for our first night. Seems to make sense for us to head counterclockwise this trip. I’m curious can we sail from Norman to VG in a day or is there a good spot to stop for the night between islands? (We’ve never sailed this section of the BVI before so I have no plans. Probably be in Anegada Nov 3-5 but who knows!

Norman to VG in a day?
Yes. If crew is slow getting off ball, say after 9:00 and desires to stop somewhere on the way (The Baths, the Dogs, etc) then making it to North Sounds would likely be better with a night stop in between.

Cooper, Marina Cay or Trellis are all good choices to use as an over night before heading to VG. Gives you time to stop at the Baths

Cooper and marina cay can be rolly and uncomfortable if you are on a Monohull.

Does anyone know the conditions of the moorings at Trellis?

There are many good moorings at Trellis.

Today we sailed from Great Harbor, Peter Island to Leverick. Left around 9:30am, arrived around 4pm. Wind was from the NE and we're on a Nautitech Open 40 cat. Wind never got above 12kts, and mostly was 9-10, but several times it dropped below 7. The direction of the wind caused us to have to tack several times and enter the channel at 135 degrees. We heading up at due N or 005 which was as deep into the wind that the boat could hold a decent speed (TW @40-50 degrees). Of course, I'm no expert sailor and none of the rest of my party are sailors at all. So everything was single-handed. Even with a bad sailor and light winds from what I would call a bad direction, you could make it from Norman to Leverick in one day.

If you're in a monohull, you could point closer to the wind and not have to tack as much, which would make it even faster.

There's really only two options for stopping - VG Marina (Spanish Town) or Trellis Bay/Marina Cay/Scrub Island. As mentioned, Marina Cay is rolly, especially because of all the boats/shuttles that run from Beef to Scrub. We spent a night at Cooper last December and it was *very* rolly (that was a monohull).

We were at The Bight night before last. The Willy-T was not open yet, but they were working on it.

Foxy's was not open yet at Great Harbor, JVD, but they said they were opening the next day so you should be good there.

From our experiences it doesn't matter where you go, it's all fun Have a great time!