30 days off to cruise! How to start Planning?

[CoolBeans]

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

[shadow]

That sounds great!! I guess it depends on what you are dying to do.. If you want to do a long sail and be out on the water, I say, do a Bermuda run then back, etc.. If you just want to do casual coastal, then the ICW is also great.. Just depends on your mood, etc.. but sound great, regardless.. Have a great time though, regardless!!!