So...3 months leave of absence was a hard sell, but 30 days off with a years notice isn't something I'm going to turn my nose up at

And since it is
vacation time, I get paid to take it
Ok, so where do I even start!
When to leave? I was thinking April or May or June? It's not overly hot, or cold, and the
weather is pretty fair. That would be a 2019 trip...so I have plenty of time to plan something
Where to go? Initial thought was just an endurance run south just to see how far I could go before I had to
head back home. Next thought was to circumnavigate the
Chesapeake Bay. It's only 200 miles to Elkton from Norfolk roughly, 2-4 days by
boat depending on how fast and how long I run. I figure in a month I could poke my nose into a bunch of cool
anchorages and towns. On the other hand, I just joined a
cruising club and one of the members was telling me about cruising the sounds of
North Carolina...
What to do? Ideas? Places to visit? Quiet backwaters to drop the hook?
Any
advice, wisdom, experiences, etc. to share are welcome! This is exciting to actually have a short term life goal