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MLS,
You could make the trip in three days, if all went well, including the weather. Without scaling it off of a chart, I'd guess the trip is about 150-160 nm.
HdG to Annapolis ~45 nm
Annapolis to Soloman's Island ~45 nm
Soloman's to D'ville ~60 nm
If you wanted the last leg to be shorter, put in to Mill Creek, off the Great Wicomico near Reedville, VA. A very pretty, quiet and secluded anchorage.
Sight-seeing stops along the way would be St. Michaels and Oxford, MD, but each would add a day to your trip.
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Hud
s/y The Belle of Virginia
Island Packet 380
Nevis, West Indies
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