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· "Nevis Nice"
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Scott,

Hudson Creek in the Little Choptank would be a well-protected anchorage that time of year. It's a nice little anchorage, quiet and isolated. I second the other suggestions about stopping in Crisfield. We always ate dinner at Fisherman's Inn there. You can anchor in the Somers Cove Marina basin, off the Coast Guard Station, but the bottom is soupy mud. You might drag if the wind kicks up to 30 kts or more.

From Crisfield, I'd suggest heading south to Onancock, at the head of Onancock Creek, about five miles off the Bay on the eastern shore of Virginia. Some good restaurants there, too. There's room to anchor, or you can tie up to the bulkhead at the little Onancock Wharf marina. It's less than 30 nm from Onancock to Deltaville. If you're not ready to end your trip, try Mill Creek, off the Great Wicomico River, south of Smith Point on the western shore in Virginia. It's very well protected from all wind directions, and fairly unpopulated by houses on the shoreline.
 

· "Nevis Nice"
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...I'd like to come down through Hooper Strait, but I'm questioning the wisdom of this. Dozier's mentions a strong current and the chart shows this route skirting the prohibited area/bombing range on Bloodsworth Island. I'm all for taking the road less traveled, but maybe there's a good reason that people don't take this route?...
Scott,

I've sailed through the Hooper Strait in light air, and the currents weren't a problem at all. I don't know if the military uses the bombing range on Bloodsworth any more. I've never seen any activity there, as opposed to the Targets on the western side of the Bay, which gets used from time to time.

Hooper Strait is a good way to get into the Sound. Just mind the markers--it has some shallow spots!
 
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