Granite,
I'm in a similar status as you - years of small boat experience, but no experience with large powerboats and wanting to transition that direction. I live on the south end of the Chesapeake Bay. I have a trawler charter set up for mid-June on a 43' motoryacht, with a training captain to teach my wife and I how to operate the thing. I chartered through C&C Charters (CCCharters.com) which is in Grasonville, MD, not too far from Annapolis. They've got at least a couple of trawler/motoryachts for charter. The training captain was arranged through US Delivery Captain, Inc. Can't give a review of either outfit yet except to say they've both been accommodating and pleasant in making the arrangements.
Hope this helps,
David B.
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