Rob, consider yourself lucky on many fronts! Congrats on the job and also welcome to the largest estuary in the US. "Welcome to Ballmore, hon." The locals append a "hon" after most sentences and it's not Balt-i-More... it's "Ball-more".
You will LOVE the Chesapeake Bay. It is a lot different than lake boating and because the Bay is an estuary the depths can be challenging and you need to be cognizant of the tides.
I grew up on the Bay and boated there for 20 years and recently moved to Charlotte where I'm a Lake boater now. I recently returned up there and realized even going across the enormous Bay I still only had depths of 15 feet with exceptions as I crossed the channel where it got up to 26 feet briefly. I have depths in my Lake up to 100'+.
So back to the Bay.... cross it. Go to the Eastern Shore. Fairlee Creek is awesome. Kent Narrows. St Michaels. Rock Hall. Wortons Creek. Hart-Miller island is fun, too (as someone previously mentioned) but it gets a little too nutty there for me and I really prefer Fairlee as there is a great bar there called Jellyfish Joels (
http://mearsgreatoaklanding.com/jellyfish-joels/). It's a blast to raft up inside the sheltered creek and relax and listen to the band playing at 'Joels.
Learn the Bay and spend the winter doing some research. There is so much to do up there I just wished the season was longer.

Good luck and congrats again.