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Lapworth,
I typically averaged 5 knots when on the bay in my Islander 26 with winds at 8 to 10 knots and I think you should be fairly safe with that assumption. I would not drop anchor in the bay as there is lots of traffic at night. There is a book called the Gunkholers Guide to the Chesapeake they is a great addition for someone wanting to explore the bay. It has all the marinas listed with services and recommended area for shelter and anchorages. There are also some recommended trip routes.
Good luck on your adventures the bay is a fun place to explore.
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