Maybe start with what you want to see and then go from there...I develop a trip "plan" based upon what the crew wants to see and build around that. Out of habit I typically take a clockwise route which probably puts me in the minority. "Plan" is in quotes because you need account for weather etc. and I have never had an actual "plan" follow the intended "plan"

As an example I am going in 2 weeks and will avoid Trellis Bay on the night of the full moon party. We will be in Anegada instead

Are you going to try and get to Anegada?