I guess it depends :-) at least in part on the weather. Last time we were there we motor sailed from JVD to North Sound (in a small monohull) which was quite pleasant but long. But conditions were calm.

We like the Clockwise route because of not being with the crowd. But MrEZ points out the downside. Counterclockwise you break down the upwind portion into smaller segments. Plus, with average weather, the sail from North Sound to Anegada is really sweet.

You could get ahead if the crowd by going from Tortola to North Sound on day 1 (perhaps with power assist) then go to Anegada the next day and so on.

Sorry I see George got in ahead of me. Honestly I didn’t plagiarize the first sentence.