Thanks for the replies. Having spent WAY too much time here and just basic web surfing about this trip, no real big surprises. I tend to over research when it comes to things like this, and I totally understand that any plan is just a starting point that will change according to the situation at hand. I am comfortable with our decision to start in Red Hook simply because the sooner we get on the boat, the better, whether we sit in port or short sail to anchor somewhere. As stated, it also gives us a little wiggle room to have a swim, snorkel, or even just sleep late the day of departure. Leverick is certain along with car, dinner, and pool, but only cuz my girls will likely need some social interaction. I would be happy not seeing a sole for the entire time..... Being a busy time of year, that will also dictate some of our plan destination plans. Thanks again for the info and confirmation. This site has been a wealth of information and look forward to putting it to use!