Hello Fair1976.
I'm a fellow stink potter and live just up I-44 from you, outside of Springfield, MO.
Here's what I would do...
After your briefings, head straight to Norman Island. It will take you maybe 1.5 hrs, which should leave you time to dinghy around to snorkel the Caves and get back in time for dinner at The Bight. Don't forget your camera. We have some of our favorite group sunset photos from there. Option: Willie T.
Next morning... after snorkeling the Indians (the earlier you get there, the less time you'll spend waiting on a ball), you can head to Marina Cay. It will take you 2-ish hrs and once there you'll find a really good mooring field. After a cheeseburger for lunch at Pusser's you can dinghy over to Trellis Bay. It's a neat place to check out. We've had dinner at Pusser's, but prefer to use this stop as one of our dinner's aboard.
Next morning... head to Leverick. A night in a slip at Leverick is always on our list and Nick, although I've never met him in person; only corresponded with him via email, is a rock star. A night on the dock there allows everyone to more easily come and go from the boat (sometimes a little space/time away from your boat mates is a good thing). Plus, you can grab additional provisions at the store there. It has always been very well stocked. Nick can hook you up with a taxi or rental car to drive to The Baths, which is way more fun than fighting for a mooring ball. Don't spend too much time there, so you can stop for a drink at Hog Heaven on your way back to Leverick for dinner upstairs. We have had some good meals there and some great meals too. Water is free with the slip, so top off if you think you'll need it.
In my opinion, I would skip Anegada this time. It's a long slog and not worth it for your first charter, especially since it's a little short. By the way, does MarineMax require approval for you to go to Anegada?
From Leverick to Jost Van Dyke will take you 3-4 hours or so, depending on whether you're a hammer down in a straight line captain&crew, or if you want to swing by Necker Island on your way out of North Sound and cruise to JVD.
JVD is a good place to spend two nights. We usually spend on night in Great Harbor where we dinghy around to White Bay and go to Soggy Dollar, then have what has always been a good dinner and good time at Corsiar's before finishing the night at Foxy's. The next day we pop over to Little Harbor, from where we can go to Sandy Spit, Foxy's Taboo and the other bar (forgot the name), and check out the Bubbly Pool before dinner at Sydney's.
Have Fun!
