I'd just go straight to Leverick Bay from RT the first afternoon. You'll have plenty of time, and can jump off to Anegada from there. If you're lucky enough to get a ball at Cooper with all the BoatyBall crap going on, you'll get there by 1-1:30 pm and really your first afternoon is sort of wasted. You'll be able to get to Anegada in a couple hours from North Sound. If it's blowing 25+ with 6-8 foot swells or a squall then I probably wouldn't go to Anegada, but that's rare, and anything below that you're fine. It's pretty much a close reach-beam reach the whole way. Great sail; you'll love it.